alpha-Methylcinnamic acid (2-Methyl-3-phenylacrylic acid) [C10H10O2] by Asch

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5 substances in Reaxys

2018-07-26 21h:42m:50s (UTC)

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Search as: As drawn ) AND (IDE.XRN=2042544) OR (IDE.XRN=2042546) OR (IDE.XRN=2042545) OR (IDE.XRN=5172722) OR (IDE.XRN=6098658))

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Reaxys ID 2042544 View in Reaxys

1/5 CAS Registry Number: 1199-77-5 Chemical Name: α-methylcinnamic acid; 2-methyl-3-phenyl-2-propenoic acid; 12-methyl-3-phenylacrylic acid; α-methyl cinnamic acid; αmethyl-cinnamic acid; 2-methyl-3-phenylacrylic acid; 2-methyl-cinnamic acid Linear Structure Formula: C10H10O2 Molecular Formula: C10H10O2 Molecular Weight: 162.188 Type of Substance: isocyclic InChI Key: XNCRUNXWPDJHGV-UHFFFAOYSA-N Note:

Substance Label (23) Label References 1

Chen, Xiang-Yu; Gao, Zhong-Hua; Song, Chun-Yu; Zhang, Chun-Lin; Wang, Zhi-Xiang; Ye, Song; Angewandte Chemie - International Edition; vol. 53; nb. 43; (2014); p. 11611 - 11615; Angew. Chem.; vol. 53; nb. 126; (2014); p. 11795 - 11799,5, View in Reaxys; Pan, Shen; Huang, Yangen; Qing, Feng-Ling; Chemistry - An Asian Journal; vol. 11; nb. 20; (2016); p. 2854 - 2858, View in Reaxys; Yu, Chunbing; Zhang, Jian; Zhong, Guofu; Chemical Communications; vol. 53; nb. 71; (2017); p. 9902 - 9905, View in Reaxys

Yang, Shuang; Che, Wen; Wu, Hui-Ling; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Science; vol. 8; nb. 3; (2017); p. 1977 - 1980, View in Reaxys

Patent; Nankai University; ZHOU, QILIN; ZHU, SHOUFEI; YANG, SHUANG; CHE, WEN; WANG, LIXIN; (15 pag.); CN106518931; (2017); (A) Chinese, View in Reaxys

13a

Rzymkowski, Jan; Piątek, Anna; Helvetica Chimica Acta; vol. 99; nb. 9; (2016); p. 665 - 673, View in Reaxys

10o

Głodek, Marta; Makal, Anna; Kłys, Arkadiusz; Zakrzewski, Janusz; Plażuk, Damian; European Journal of Organic Chemistry; vol. 2016; nb. 24; (2016); p. 4215 - 4223, View in Reaxys

Guan, Zaihong; Lu, Shengmei; Li, Can; Journal of Catalysis; vol. 311; (2014); p. 1 - 5, View in Reaxys; Agasti, Soumitra; Sharma, Upendra; Naveen, Togati; Maiti, Debabrata; Chemical Communications; vol. 51; nb. 25; (2015); p. 5375 - 5378, View in Reaxys

Knaus, Tanja; Mutti, Francesco G.; Humphreys, Luke D.; Turner, Nicholas J.; Scrutton, Nigel S.; Organic and Biomolecular Chemistry; vol. 13; nb. 1; (2015); p. 223 - 233, View in Reaxys

Gandeepan, Parthasarathy; Rajamalli, Pachaiyappan; Cheng, Chien-Hong; Chemistry - A European Journal; vol. 21; nb. 25; (2015); p. 9198 - 9203, View in Reaxys

Hou, Jing; Xie, Jian-Hua; Zhou, Qi-Lin; Angewandte Chemie - International Edition; vol. 54; nb. 21; (2015); p. 6302 - 6305; Angew. Chem.; vol. 127; nb. 21; (2015); p. 6400 - 6403,4, View in Reaxys

Liu, Le; Zhang-Negrerie, Daisy; Du, Yunfei; Zhao, Kang; Synthesis (Germany); vol. 47; nb. 19; (2015); p. 2924 2930; Art.No: SS-2015-C0218-ST, View in Reaxys

Prakash, Rashmi; Shekarrao, Kommuri; Gogoi, Sanjib; Organic Letters; vol. 17; nb. 21; (2015); p. 5264 - 5267, View in Reaxys

MCA

Sun, Xiaojing; Monnier, John R.; Williams, Christopher T.; Catalysis Letters; vol. 143; nb. 9; (2013); p. 881 - 886, View in Reaxys; Zirakzadeh, Afrooz; Gross, Manuela A.; Wang, Yaping; Mereiter, Kurt; Weissensteiner, Walter; Organometallics; vol. 33; nb. 8; (2014); p. 1945 - 1952, View in Reaxys

Khumsubdee, Sakunchai; Burgess, Kevin; Tetrahedron; vol. 70; nb. 6; (2014); p. 1326 - 1335, View in Reaxys

3t'

Zhang, Shuting; Zhang, Xiaohui; Ling, Xuege; He, Chao; Huang, Ruofeng; Pan, Jing; Li, Jiaqiang; Xiong, Yan; RSC Advances; vol. 4; nb. 58; (2014); p. 30768 - 30774, View in Reaxys

Zhang, Lingjuan; Qiu, Ruiying; Xue, Xiao; Pan, Yixiao; Xu, Conghui; Wang, Doudou; Wang, Xinyu; Xu, Lijin; Li, Huanrong; Chemical Communications; vol. 50; nb. 82; (2014); p. 12385 - 12388, View in Reaxys

Sasmal, Aniruddha; Taniguchi, Tsuyoshi; Wipf, Peter; Curran, Dennis P.; Canadian Journal of Chemistry; vol. 91; nb. 1; (2013); p. 1 - 5, View in Reaxys

47a

Wang, Zhi-Gang; Chen, Liqun; Chen, Jiebo; Zheng, Jian-Feng; Gao, Weiwei; Zeng, Zhiping; Zhou, Hu; Zhang, Xiao-Kun; Huang, Pei-Qiang; Su, Ying; European Journal of Medicinal Chemistry; vol. 62; (2013); p. 632 - 648, View in Reaxys

Moiseev, Dmitry V.; James, Brian R.; Gushchin, Aleksey V.; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 188; nb. 6; (2013); p. 678 - 690, View in Reaxys

Patent; Zhejiang Jiuzhou Pharmaceutical Co., Ltd.; EP2275398; (2011); (A1) English, View in Reaxys

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Patent; Lotz, Matthias; Spindler, Felix; US2008/287698; (2008); (A1) English, View in Reaxys

Zhao, Xiaodan; Alper, Howard; Yu, Zhengkun; Journal of Organic Chemistry; vol. 71; nb. 10; (2006); p. 3988 - 3990, View in Reaxys

RPR1

Verma, Raman K.; Singla, Rubina; Punniyakoti; Medicinal Chemistry Research; vol. 13; nb. 8-9; (2004); p. 660 676, View in Reaxys

2a (CA)

Basel, Yochai; Hassner, Alfred; Tetrahedron Letters; vol. 43; nb. 14; (2002); p. 2529 - 2533, View in Reaxys

Patent-Specific Data (5) Prophetic ComReferences pound Patent; Nankai University; ZHOU, QILIN; ZHU, SHOUFEI; YANG, SHUANG; CHE, WEN; WANG, LIXIN; (15 pag.); CN106518931; (2017); (A) Chinese, View in Reaxys Patent; Central South University; TANG, ZHEN YU; LI, CHENG TAN; YUAN, XI; (18 pag.); CN105646119; (2016); (A) Chinese, View in Reaxys Patent; CHINA MEDICAL UNIVERSITY; MENG, FANHAO; HE, XIN; CAO, CHONG; LIANG, JINGWEI; ZHANG, TINGJIAN; (10 pag.); CN106045827; (2016); (A) Chinese, View in Reaxys prophetic product

Patent; VERENIUM CORPORATION; US2011/27346; (2011); (A1) English, View in Reaxys; Patent; Weiner, David P.; Varvak, Alexander; Richardson, Toby; Podar, Mircea; Burke, Ellen; Healey, Shaun; US2012/177722; (2012); (A1) English, View in Reaxys Patent; The Scripps Research Institute; US6350905; (2002); (B1) English, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.09

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

37.3

Lipinski Number

Veber Number

Related Structure (3) Related Structure References Wie von.

Stoermer; Voht; Justus Liebigs Annalen der Chemie; vol. 409; (1915); p. 42, View in Reaxys

Zur Struktur.

Fittig; Jayne; Justus Liebigs Annalen der Chemie; vol. 216; (1883); p. 103, View in Reaxys; Conrad; Bischoff; Justus Liebigs Annalen der Chemie; vol. 204; (1880); p. 180, View in Reaxys; Fittig; Chemische Berichte; vol. 16; (1883); p. 1437, View in Reaxys; Fittig; Justus Liebigs Annalen der Chemie; vol. 195; (1879); p. 171, View in Reaxys

gezeigt worden ist, Beilstein Handbook, View in Reaxys sind die bei 74grad und 81grad schmelzenden Formen konfigurativ identisch und entsprechen sterisch der gewoehnlichen (trans-)Zimtsaeure. Derivative (2) Comment (Derivative)

References

S-Benzyl-isothiuro- Jart; Acta Polytechnica Scandinavica, Chemistry Including Metallurgy Series; vol. 24; (1963); p. 1,19,97, nium-salz v. FrieView in Reaxys diger , Pedersen , Acta chem. scand. 9 (1955) 1425 ist 3Phenyl-crotonsaeure-S-Benzylisothiuronium-Salz S-Benzyl-isothiuro- Jart; Acta Polytechnica Scandinavica, Chemistry Including Metallurgy Series; vol. 24; (1963); p. 1,19,97, nium-salz o. FrieView in Reaxys

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diger , Pedersen , Acta chem. scand. 9 (1955) 1425 ist 3Phenyl-crotonsaeure-S-Benzylisothiuronium-Salz Melting Point (18) 1 of 18

Melting Point [°C]

80 - 82

Solvent (Melting Point)

hexane; ethyl acetate

Wang, Zhi-Gang; Chen, Liqun; Chen, Jiebo; Zheng, Jian-Feng; Gao, Weiwei; Zeng, Zhiping; Zhou, Hu; Zhang, XiaoKun; Huang, Pei-Qiang; Su, Ying; European Journal of Medicinal Chemistry; vol. 62; (2013); p. 632 - 648, View in Reaxys 2 of 18

Melting Point [°C]

79 - 81

Verma, Raman K.; Singla, Rubina; Punniyakoti; Medicinal Chemistry Research; vol. 13; nb. 8-9; (2004); p. 660 - 676, View in Reaxys 3 of 18

Melting Point [°C]

Solvent (Melting Point)

methanol

Ganushchak, N. I.; Obushak, N. D.; Polishchuk, O. P.; Journal of Organic Chemistry USSR (English Translation); vol. 22; nb. 12; (1986); p. 2291 - 2295; Zhurnal Organicheskoi Khimii; vol. 22; nb. 12; (1986); p. 2554 - 2558, View in Reaxys 4 of 18

Melting Point [°C]

79 - 80.5

Kuchar et al.; Collection of Czechoslovak Chemical Communications; vol. 44; (1979); p. 183,186, View in Reaxys 5 of 18

Melting Point [°C]

79 - 80

Kingsbury,C.A.; Max,G.; Journal of Organic Chemistry; vol. 43; (1978); p. 3131 - 3139, View in Reaxys 6 of 18

Melting Point [°C]

78.5 - 79

Eagen,M.C.; Cromwell,N.H.; Journal of Organic Chemistry; vol. 39; (1974); p. 3863 - 3866, View in Reaxys 7 of 18

Melting Point [°C]

77 - 78

Bayssat et al.; Chimica Therapeutica; vol. 8; (1973); p. 202, View in Reaxys 8 of 18

Melting Point [°C]

79 - 80

Solvent (Melting Point)

ethanol; H2O

Kuchar; Grimova; Roubal; et al.; Cesko-Slovenska Farmacie; vol. 22; nb. 9; (1973); p. 388 - 394, View in Reaxys 9 of 18

Melting Point [°C]

Muller,J.-C.; Fleury,J.-P.; Bulletin de la Societe Chimique de France; (1970); p. 738 - 742, View in Reaxys 10 of 18

Melting Point [°C]

79.5 - 80.5

Bos; Arens; Recueil des Travaux Chimiques des Pays-Bas; vol. 82; (1963); p. 339,345, View in Reaxys 11 of 18

Melting Point [°C]

Solvent (Melting Point)

benzene

Raikow; Chemische Berichte; vol. 20; (1887); p. 3397, View in Reaxys; Dain; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 29; (1897); p. 607,609; Chem. Zentralbl.; vol. 69; nb. I; (1898); p. 674, View in Reaxys 12 of 18

Melting Point [°C]

Solvent (Melting Point)

CS2

Melting Point [°C]

Solvent (Melting Point)

ethanol

Melting Point [°C]

Solvent (Melting Point)

H2O

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Melting Point [°C]

81 - 82

Solvent (Melting Point)

H2O

Melting Point [°C]

81 - 82

Solvent (Melting Point)

acetic acid

Melting Point [°C]

81 - 82

Solvent (Melting Point)

diethyl ether

Melting Point [°C]

81 - 82

Solvent (Melting Point)

petroleum ether

References Conrad; Bischoff; Justus Liebigs Annalen der Chemie; vol. 204; (1880); p. 180, View in Reaxys; Dain; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 29; (1897); p. 607,609; Chem. Zentralbl.; vol. 69; nb. I; (1898); p. 674, View in Reaxys

Association (MCS) (1) 1 of 1

Description (Association (MCS))

Association with compound

Obtemperanskaya; Aziz; J. Anal. Chem. USSR (Engl. Transl.); vol. 31; (1976); p. 295, View in Reaxys Chromatographic Data (1) Chromatographic References data HPLC (High performance liquid chromatography)

Zirakzadeh, Afrooz; Gross, Manuela A.; Wang, Yaping; Mereiter, Kurt; Weissensteiner, Walter; Organometallics; vol. 33; nb. 8; (2014); p. 1945 - 1952, View in Reaxys; Volovych; Kasaka; Schwarze; Nairoukh; Blum; Fanun; Avnir; Schomaecker; Journal of Molecular Catalysis A: Chemical; vol. 393; (2014); p. 210 - 221, View in Reaxys

Circular Dichroism (1) References Paiaro; Pandolfo; Gazzetta Chimica Italiana; vol. 107; (1977); p. 467,469, View in Reaxys Crystal Property Description (1) Colour & Other References Properties yellow

Dissociation Exponent (3) 1 of 3

Comment (Dissociation Exponent)

(pk')6.70 (45grad; 80percent Methylcellosolve; potentiometrisch)

Kuchar et al.; Cesko-Slovenska Farmacie; vol. 29; (1980); p. 281, View in Reaxys 2 of 3

Comment (Dissociation Exponent)

(pk')pKa-Werte

Kuchar et al.; Collection of Czechoslovak Chemical Communications; vol. 40; (1975); p. 3545,3550, View in Reaxys 3 of 3

Comment (Dissociation Exponent)

(pk')pK(a): 6.35

Kuchar; Grimova; Roubal; et al.; Cesko-Slovenska Farmacie; vol. 22; nb. 9; (1973); p. 388 - 394, View in Reaxys

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Further Information (1) Description (FurReferences ther Information) Further information Jart; Acta Polytechnica Scandinavica, Chemistry Including Metallurgy Series; vol. 24; (1963); p. 1,19,97, View in Reaxys Solubility (MCS) (1) 1 of 1

Solubility [g·l-1]

1.191

Saturation

in solution

Solvent (Solubility (MCS))

H2O

Comment (Solubility (MCS))

in boiling solvent.

Conrad; Bischoff; Justus Liebigs Annalen der Chemie; vol. 204; (1880); p. 180, View in Reaxys NMR Spectroscopy (9) 1 of 9

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 400 scopy) [MHz] Location

supporting information

Hou, Jing; Xie, Jian-Hua; Zhou, Qi-Lin; Angewandte Chemie - International Edition; vol. 54; nb. 21; (2015); p. 6302 - 6305; Angew. Chem.; vol. 127; nb. 21; (2015); p. 6400 - 6403,4, View in Reaxys 2 of 9

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 100 scopy) [MHz] Location

supporting information

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 400 scopy) [MHz] Wang, Zhi-Gang; Chen, Liqun; Chen, Jiebo; Zheng, Jian-Feng; Gao, Weiwei; Zeng, Zhiping; Zhou, Hu; Zhang, XiaoKun; Huang, Pei-Qiang; Su, Ying; European Journal of Medicinal Chemistry; vol. 62; (2013); p. 632 - 648, View in Reaxys 4 of 9

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

13C

Coupling Nuclei

19F

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Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 100 scopy) [MHz] Wang, Zhi-Gang; Chen, Liqun; Chen, Jiebo; Zheng, Jian-Feng; Gao, Weiwei; Zeng, Zhiping; Zhou, Hu; Zhang, XiaoKun; Huang, Pei-Qiang; Su, Ying; European Journal of Medicinal Chemistry; vol. 62; (2013); p. 632 - 648, View in Reaxys 5 of 9

Description (NMR Spectroscopy)

Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

CDCl3

Frequency (NMR Spectro- 75 scopy) [MHz] Zhao, Xiaodan; Alper, Howard; Yu, Zhengkun; Journal of Organic Chemistry; vol. 71; nb. 10; (2006); p. 3988 - 3990, View in Reaxys 6 of 9

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

CDCl3

Frequency (NMR Spectro- 75 scopy) [MHz] Zhao, Xiaodan; Alper, Howard; Yu, Zhengkun; Journal of Organic Chemistry; vol. 71; nb. 10; (2006); p. 3988 - 3990, View in Reaxys 7 of 9

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectroscopy)

CDCl3

Frequency (NMR Spectro- 300 scopy) [MHz] Zhao, Xiaodan; Alper, Howard; Yu, Zhengkun; Journal of Organic Chemistry; vol. 71; nb. 10; (2006); p. 3988 - 3990, View in Reaxys 8 of 9

Description (NMR Spectroscopy)

Spectrum

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectroscopy)

CDCl3

Frequency (NMR Spectro- 300 scopy) [MHz] Zhao, Xiaodan; Alper, Howard; Yu, Zhengkun; Journal of Organic Chemistry; vol. 71; nb. 10; (2006); p. 3988 - 3990, View in Reaxys 9 of 9

Description (NMR Spectroscopy)

NMR

Muller; Fleury; Bulletin de la Societe Chimique de France; (1970); p. 738, View in Reaxys; Sakakibara et al.; Journal of Organic Chemistry; vol. 35; (1970); p. 3884,3886, View in Reaxys IR Spectroscopy (3) 1 of 3

Description (IR Spectroscopy)

Bands

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Solvent (IR Spectroscopy)

potassium bromide

Comment (IR Spectroscopy)

film

Description (IR Spectroscopy)

ATR-FTIR (attenuated total reflectance Fourier transform infrared spectroscopy); Bands; Spectrum

Solvent (IR Spectroscopy)

dichloromethane

Sun, Xiaojing; Williams, Christopher T.; Catalysis Communications; vol. 17; (2012); p. 13 - 17, View in Reaxys 3 of 3

Description (IR Spectroscopy)

Muller; Fleury; Bulletin de la Societe Chimique de France; (1970); p. 738, View in Reaxys; Kuchar; Grimova; Roubal; et al.; Cesko-Slovenska Farmacie; vol. 22; nb. 9; (1973); p. 388 - 394, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) electrospray ionisa- Wang, Zhi-Gang; Chen, Liqun; Chen, Jiebo; Zheng, Jian-Feng; Gao, Weiwei; Zeng, Zhiping; Zhou, Hu; Zhang, tion (ESI); liquid Xiao-Kun; Huang, Pei-Qiang; Su, Ying; European Journal of Medicinal Chemistry; vol. 62; (2013); p. 632 - 648, chromatography View in Reaxys mass spectrometry (LCMS); spectrum UV/VIS Spectroscopy (3) 1 of 3

Description (UV/VIS Spectroscopy)

Absorption maxima

Absorption Maxima (UV/ VIS) [nm]

256

Bergstrom, Donald E.; Inoue, Hideo; Reddy, P. Anantha; Journal of Organic Chemistry; vol. 47; nb. 11; (1982); p. 2174 2178, View in Reaxys 2 of 3

Description (UV/VIS Spectroscopy)

UV/VIS

Kuchar; Grimova; Roubal; et al.; Cesko-Slovenska Farmacie; vol. 22; nb. 9; (1973); p. 388 - 394, View in Reaxys 3 of 3

Description (UV/VIS Spectroscopy)

Absorption maxima

Charney; Bernhard; Journal of the American Chemical Society; vol. 89; nb. 11; (1967); p. 2726 - 2733, View in Reaxys Use (1) Laboratory Use and References Handling Stabilisierung von Erythrocyten

Kuchar et al.; Collection of Czechoslovak Chemical Communications; vol. 40; (1975); p. 3545,3550, View in Reaxys

Reaxys ID 2042545 View in Reaxys

2/5 CAS Registry Number: 15250-29-0 Chemical Name: (Z)-2-methyl-3-phenylprop-2-enoic acid; (Z)-2methyl-3-phenyl-2-propenoic acid; (Z)-2-methyl-3-phenylacrylic acid; (Z)-2-methyl-3-phenyl-acrylic acid; 2-methyl-3c-phenyl-acrylic acid; 2-Methyl-3c-phenyl-acrylsaeure; α-Methyl-cis-zimtsaeure Linear Structure Formula: C10H10O2 Molecular Formula: C10H10O2 Molecular Weight: 162.188 Type of Substance: isocyclic InChI Key: XNCRUNXWPDJHGV-FPLPWBNLSA-N Note:

Substance Label (8)

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Label

References

2a''

Hou, Jing; Ee, Aloysius; Feng, Wei; Xu, Jin-Hui; Zhao, Yu; Wu, Jie; Journal of the American Chemical Society; vol. 140; nb. 15; (2018); p. 5257 - 5263, View in Reaxys

cis-17

Abe, Masato; Nishikawa, Keisuke; Okuda, Katsuhiro; Shindo, Mitsuru; Fukuda, Hiroshi; Nakanishi, Kazunari; Tazawa, Yuta; Taniguchi, Tomoya; Park, So-Young; Hiradate, Syuntaro; Fujii, Yoshiharu; Phytochemistry (Elsevier); vol. 84; (2012); p. 56 - 67,12, View in Reaxys

Katritzky, Alan R.; Majumder, Suman; Jain, Ritu; Journal of the Indian Chemical Society; vol. 80; nb. 11; (2003); p. 1073 - 1075, View in Reaxys

(Z)-83

Rudler, Henri; Durand-Reville, Thomas; Journal of Organometallic Chemistry; vol. 617; nb. 1; (2001); p. 571 - 587, View in Reaxys

13 Z (R=C6H5)

Aumann, Rudolf; Weidenhaupt, Hermann-Josef; Chemische Berichte; vol. 120; (1987); p. 23 - 28, View in Reaxys

Z-(16)

Vineyard,B.D. et al.; Journal of the American Chemical Society; vol. 99; (1977); p. 5946 - 5952, View in Reaxys

Z=cis

Klein; Levene; Journal of the American Chemical Society; vol. 94; (1972); p. 2520, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.09

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

37.3

Lipinski Number

Veber Number

Related Structure (1) References Culp et al.; Journal of Organic Chemistry; vol. 38; (1973); p. 2945,2948, View in Reaxys; Klein; Levene; Journal of the American Chemical Society; vol. 94; (1972); p. 2520, View in Reaxys Melting Point (13) 1 of 13

Melting Point [°C]

82 - 83

Solvent (Melting Point)

dichloromethane; hexane

Melting Point [°C]

92 - 93

Vineyard,B.D. et al.; Journal of the American Chemical Society; vol. 99; (1977); p. 5946 - 5952, View in Reaxys 3 of 13

Melting Point [°C]

90 - 91

Culp et al.; Journal of Organic Chemistry; vol. 38; (1973); p. 2945,2948, View in Reaxys 4 of 13

Melting Point [°C]

91 - 92

Figuera et al.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1972); p. 1434,1439, View in Reaxys 5 of 13

Melting Point [°C]

91 - 92

Solvent (Melting Point)

petroleum ether

Sandris; Tetrahedron; vol. 24; (1968); p. 3583, View in Reaxys 6 of 13

Melting Point [°C]

93 - 95

Singer; Kong; Journal of the American Chemical Society; vol. 88; (1966); p. 5213,5214, View in Reaxys 7 of 13

Melting Point [°C]

78 - 79

Rand,L.; Dolinski,R.J.; Journal of Organic Chemistry; vol. 31; (1966); p. 4061 - 4066, View in Reaxys 8 of 13

Melting Point [°C]

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Urushibara; Hirota; Nippon Kagaku Zasshi; vol. 82; (1961); p. 351,360; Chem.Abstr.; vol. 56; nb. 10025; (1962), View in Reaxys 9 of 13

Melting Point [°C]

Urushibara; Hirota; Nippon Kagaku Zasshi; vol. 82; (1961); p. 351,360; Chem.Abstr.; vol. 56; nb. 10025; (1962), View in Reaxys 10 of 13

Melting Point [°C]

92 - 93

Solvent (Melting Point)

petroleum ether

Mangini; Montanari; Gazzetta Chimica Italiana; vol. 88; (1958); p. 1081,1088 Tab., View in Reaxys 11 of 13

Melting Point [°C]

90 - 92

Solvent (Melting Point)

petroleum ether

Carpino; Journal of the American Chemical Society; vol. 80; (1958); p. 599, View in Reaxys 12 of 13

Melting Point [°C]

Solvent (Melting Point)

H2O

Fusco; Rossi; Gazzetta Chimica Italiana; vol. 78; (1948); p. 524,533, View in Reaxys 13 of 13

Melting Point [°C]

91 - 92

Solvent (Melting Point)

light petroleum

Stoermer; Voht; Justus Liebigs Annalen der Chemie; vol. 409; (1915); p. 42, View in Reaxys Crystal Property Description (2) Colour & Other References Properties colourless

Blaettchen

Fusco; Rossi; Gazzetta Chimica Italiana; vol. 78; (1948); p. 524,533, View in Reaxys

Dissociation Exponent (2) 1 of 2

Comment (Dissociation Exponent)

(k')

Sandris; Tetrahedron; vol. 24; (1968); p. 3583, View in Reaxys 2 of 2

Comment (Dissociation Exponent)

(pk')pK: 5.10 in 50percentig. wss. A. bei 25+-1grad

Hogeveen; Recueil des Travaux Chimiques des Pays-Bas; vol. 83; (1964); p. 813,814, View in Reaxys Electrochemical Behaviour (1) Description (Elec- Comment (Electrotrochemical Behav- chemical Behaviour) iour) Electrolytic dissoci- in wss. Aceton. ation / protonation equilibrium

References

Kleene; Westheimer; Wheland; Journal of the American Chemical Society; vol. 63; (1941); p. 791, View in Reaxys

Further Information (1) Description (FurReferences ther Information) Further information Valente; Wolfhagen; Journal of Organic Chemistry; vol. 31; (1966); p. 2509,2510,2511, View in Reaxys Solubility (MCS) (1) 1 of 1

Temperature (Solubility (MCS)) [°C]

Solvent (Solubility (MCS))

light petroleum

Comment (Solubility (MCS))

Solubility :0.76 percent.

Stoermer; Voht; Justus Liebigs Annalen der Chemie; vol. 409; (1915); p. 42, View in Reaxys NMR Spectroscopy (7)

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1 of 7

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 400 scopy) [MHz] Location

supporting information

Hou, Jing; Ee, Aloysius; Feng, Wei; Xu, Jin-Hui; Zhao, Yu; Wu, Jie; Journal of the American Chemical Society; vol. 140; nb. 15; (2018); p. 5257 - 5263, View in Reaxys 2 of 7

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 400 scopy) [MHz] Original Text (NMR Spec- 1H NMR (CDCl3, 400 MHz) α: 2.12 (d, J = 1.4 Hz, 3H, -CH3), 6.86 (q, J = 1.4 Hz, 1H, Ar-CH=), troscopy) 7.20-7.36 (m, 5H, Ar-H) Signals [ppm]

2.12; 6.86; 7.2 - 7.36

Kind of signal

d, J = 1.4 Hz, 3H, -CH&3%; q, J = 1.4 Hz, 1H, Ar-CH=; m, 5H, Ar-H

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 100 scopy) [MHz] Original Text (NMR Spec- 13C NMR (CDCl3, 100 MHz) α: 21.5 (q, -CH3), 128.0 (d, Ar), 128.1 (s, =C(CH3)-CO2-), 128.3 (d, troscopy) Ar), 128.4 (d, Ar), 135.9 (s, Ar), 137.7 (d, Ar-CH=), 172.5 (s, C=O) Signals [ppm]

21.5; 128; 128.1; 128.3; 128.4; 135.9; 137.7; 172.5

Kind of signal

q, -CH&3%; d, Ar; s, =C(CH&3%)-CO&2%-; d, Ar; d, Ar; s, Ar; d, Ar-CH=; s, C=O

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectroscopy)

CDCl3

Frequency (NMR Spectro- 400 scopy) [MHz] Rudler, Henri; Durand-Reville, Thomas; Journal of Organometallic Chemistry; vol. 617; nb. 1; (2001); p. 571 - 587, View in Reaxys

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5 of 7

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectroscopy)

CDCl3

Frequency (NMR Spectro- 400 scopy) [MHz] Rudler, Henri; Durand-Reville, Thomas; Journal of Organometallic Chemistry; vol. 617; nb. 1; (2001); p. 571 - 587, View in Reaxys 6 of 7

Description (NMR Spectroscopy)

NMR

Culp et al.; Journal of Organic Chemistry; vol. 38; (1973); p. 2945,2948, View in Reaxys; Klein; Levene; Journal of the American Chemical Society; vol. 94; (1972); p. 2520, View in Reaxys; Figuera et al.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1972); p. 1434,1439, View in Reaxys; Singer; Kong; Journal of the American Chemical Society; vol. 88; (1966); p. 5213,5214, View in Reaxys 7 of 7

Description (NMR Spectroscopy)

NMR

Comment (NMR Spectroscopy)

Culp et al.; Journal of Organic Chemistry; vol. 38; (1973); p. 2945,2948, View in Reaxys IR Spectroscopy (2) 1 of 2

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Original Text (IR Spectroscopy)

IR (KBr) 1684 cm-1

Description (IR Spectroscopy)

Figuera et al.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1972); p. 1434,1439, View in Reaxys Mass Spectrometry (2) Description (Mass Peak Spectrometry)

References

electron impact (EI); spectrum

162 m/z

high resolution mass spectrometry (HRMS); electron impact (EI); spectrum

162.0679 m/z

UV/VIS Spectroscopy (3) 1 of 3

Description (UV/VIS Spectroscopy)

Absorption maxima

Urushibara; Hirota; Nippon Kagaku Zasshi; vol. 82; (1961); p. 351,360; Chem.Abstr.; vol. 56; nb. 10025; (1962), View in Reaxys 2 of 3

Description (UV/VIS Spectroscopy)

Absorption maxima

Solvent (UV/VIS Spectroscopy)

ethanol

Mangini; Montanari; Gazzetta Chimica Italiana; vol. 88; (1958); p. 1081,1088 Tab., View in Reaxys

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3 of 3

Description (UV/VIS Spectroscopy)

Absorption maxima

Solvent (UV/VIS Spectroscopy)

aq. NaOH

Mangini; Montanari; Gazzetta Chimica Italiana; vol. 88; (1958); p. 1081,1088 Tab., View in Reaxys Medchem (1) 1 of 1

Substance Effect

Proliferative

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

root growth; inhibition ofseedlings of Lactuca sativacv. Grear Laks 366, lettuce

Substance RN

2042545View in Reaxys

Measurement Parameter

EC50

Unit

µM

Quantitative value

5.9

Measurement pX

5.23

Reaxys ID 2042546 View in Reaxys

3/5 CAS Registry Number: 1895-97-2 Chemical Name: 2-methyl-3-phenylacrylic acid Linear Structure Formula: HO2CC(CH3)CH(C6H5) Molecular Formula: C10H10O2 Molecular Weight: 162.188 Type of Substance: isocyclic InChI Key: XNCRUNXWPDJHGV-BQYQJAHWSA-N Note:

Substance Label (58) Label References 2a

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2l'

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CAD

Pavić, Kristina; Perković, Ivana; Gilja, Petra; Kozlina, Filip; Ester, Katja; Kralj, Marijeta; Schols, Dominique; Hadjipavlou-Litina, Dimitra; Pontiki, Eleni; Zorc, Branka; Molecules; vol. 21; nb. 12; (2016); Art.No: 21121629, View in Reaxys

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trans-17

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Moberg, Viktor; Duquesne, Robin; Roehrs, Oliver; Nachtigall, Jonny; Nordlander, Ebbe; Contaldi, Simone; Monari, Magda; Damoense, Llewellyn; Green, Michael; Hutton, Alan T.; Santelia, Daniela; Haukka, Matti; Chemistry--A European Journal; vol. 18; nb. 39; (2012); p. 12458 - 12478,21, View in Reaxys

acid, tab 1/3

Akritopoulou-Zanze, Irini; Whitehead, Alan; Waters, Jan E.; Henry, Rodger F.; Djuric, Stevan W.; Tetrahedron Letters; vol. 48; nb. 20; (2007); p. 3549 - 3552, View in Reaxys

Product, Tab.1, run 25

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starting to 2h

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26b

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Patent; UMICORE AG and CO. KG; WO2005/108409; (2005); (A2) English, View in Reaxys

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MCA

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7 (R = Ph, R' = Me) Soloshonok, Vadim A.; Ueki, Hisanori; Tiwari, Rohit; Cai, Chaozhong; Hruby, Victor J.; Journal of Organic Chemistry; vol. 69; nb. 15; (2004); p. 4984 - 4990, View in Reaxys educt to 1b

Lopez, Miguel A.; Rodriguez, Zalua; Gonzalez, Maritza; Tolon, Blanca; Avila, Rizette; Gonzalez, Ileana; Garmendia, Leonor; Mamposo, Taimirys; Carrasco, Ramon; Pellon, Rolando; Velez, Herman; Fini, Adamo; European Journal of Medicinal Chemistry; vol. 39; nb. 8; (2004); p. 657 - 664, View in Reaxys

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(E)-12a

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1, R=Ph, R2=Me

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Acid, Table, entry 8 You; Lee; Synlett; nb. 1; (2001); p. 105 - 107, View in Reaxys (E)-83

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carb. acid, Scheme 5

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1, Tab. 2, entry 15

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ac.for acyl azide,eq.3

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19e

Brunner, Henri; Schmidt, Peter; European Journal of Organic Chemistry; nb. 11; (2000); p. 2119 - 2133, View in Reaxys

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Patent-Specific Data (1) Location in Patent References Claim

Patent; Oridigm Corporation; US6172261; (2001); (B2) English, View in Reaxys; Patent; Ono Pharmaceutical Co., Ltd.; US6262114; (2001); (B1) English, View in Reaxys; Patent; Avon Products, Inc.; US5951990; (1999); (A) English, View in Reaxys; Patent; Lai, Yu-Chin; Quinn, Edmond T.; US2003/134977; (2003); (A1) English, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.09

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

37.3

Lipinski Number

Veber Number

Related Structure (3) Related Structure References Klein; Levene; Journal of the American Chemical Society; vol. 94; (1972); p. 2520, View in Reaxys Diese beiden Saeuren stehen nach.

Stoermer; Voht; Justus Liebigs Annalen der Chemie; vol. 409; (1915); p. 42, View in Reaxys

im Verhaeltnis der Dimorphie..

Beilstein Handbook, View in Reaxys

Derivative (1) Comment (Derivative)

References

Salz mit Piperazin Psarrea et al.; Bulletin de la Societe Chimique de France; (1961); p. 2152, View in Reaxys 2 C10H10O2*C4H10 N2: F: 130grad (aus Isopropanol, korr., Maquenne-Block); loesl. in Me., A., wl. in Acn., Chlf., unl. in Ae. und W. Melting Point (27) 1 of 27

Melting Point [°C]

59 - 61

Song, Cai-Xia; Chen, Ping; Tang, Yu; RSC Advances; vol. 7; nb. 19; (2017); p. 11233 - 11243, View in Reaxys 2 of 27

Melting Point [°C]

78 - 80

Location

supporting information

Wang, Xueqiang; Nakajima, Masaki; Martin, Ruben; Journal of the American Chemical Society; vol. 137; nb. 28; (2015); p. 8924 - 8927, View in Reaxys 3 of 27

Melting Point [°C]

70 - 72

Beesu, Mallesh; Periasamy, Mariappan; Journal of Organometallic Chemistry; vol. 705; (2012); p. 30 - 33, View in Reaxys 4 of 27

Melting Point [°C]

82 - 83

Solvent (Melting Point)

dichloromethane; hexane

Melting Point [°C]

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Solvent (Melting Point)

ethanol; H2O

Cristau; Taillefer; Tetrahedron; vol. 54; nb. 8; (1998); p. 1507 - 1522, View in Reaxys 6 of 27

Melting Point [°C]

79 - 80

Teulade, Marie-Paule; Savignac, Philippe; About-Jaudet, Elie; Collignon, Nooel; Synthetic Communications; vol. 19; nb. 1, 2; (1989); p. 71 - 82, View in Reaxys 7 of 27

Melting Point [°C]

Urushibara; Hirota; Nippon Kagaku Zasshi; vol. 82; (1961); p. 351,360; Chem.Abstr.; vol. 56; nb. 10025; (1962), View in Reaxys; Somasekharan, K. N.; Kiefer, Edgar F.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 27; nb. 1-12; (1988); p. 29 - 37, View in Reaxys 8 of 27

Melting Point [°C]

Solvent (Melting Point)

aq. ethanol

Comment (Melting Point)

Modifikation F: 74grad (s. H 615; E I 255; E II 409; E III 2764) konnte nicht wieder erhalten werden.

Bryan; White; Acta Crystallographica; vol. <B> 38; (1982); p. 1332, View in Reaxys 9 of 27

Melting Point [°C]

81.85

Solvent (Melting Point)

aq. ethanol

Bryan, Robert F.; White, Deborah H.; Acta Crystallographica, Section B: Structural Crystallography and Crystal Chemistry; vol. 38; (1982); p. 1332 - 1334, View in Reaxys 10 of 27

Melting Point [°C]

80 - 81

Julia,M.; Binet du Jassonneix,C.; Bulletin de la Societe Chimique de France; (1975); p. 743 - 750, View in Reaxys; Vaidyanathaswamy et al.; Journal of Agricultural and Food Chemistry; vol. 25; (1977); p. 1401,1402, View in Reaxys; Aguiar et al.; Journal of Organic Chemistry; vol. 41; nb. 9; (1976); p. 1545,1547, View in Reaxys; Onuma, Ken-ichi; Ito, Tomiyasu; Nakamura, Asao; Bulletin of the Chemical Society of Japan; vol. 53; nb. 7; (1980); p. 2012 - 2015, View in Reaxys 11 of 27

Melting Point [°C]

81 - 82

Solvent (Melting Point)

aq. ethanol

Brand, Richard A.; Mulvaney, J. E.; Journal of Organic Chemistry; vol. 45; nb. 4; (1980); p. 633 - 636, View in Reaxys 12 of 27

Melting Point [°C]

97 - 98

Dzurilla,M. et al.; Collection of Czechoslovak Chemical Communications; vol. 42; (1977); p. 2938 - 2944, View in Reaxys 13 of 27

Melting Point [°C]

79 - 81

Vineyard,B.D. et al.; Journal of the American Chemical Society; vol. 99; (1977); p. 5946 - 5952, View in Reaxys 14 of 27

Melting Point [°C]

81 - 83

Bright et al.; Journal of Organic Chemistry; vol. 38; (1973); p. 2554, View in Reaxys 15 of 27

Melting Point [°C]

79.5 - 80.5

Bisson,R. et al.; Canadian Journal of Chemistry; vol. 50; (1972); p. 2851 - 2858, View in Reaxys 16 of 27

Melting Point [°C]

Solvent (Melting Point)

petroleum ether

Sandris; Tetrahedron; vol. 24; (1968); p. 3583, View in Reaxys 17 of 27

Melting Point [°C]

81 - 82

Canceill,J. et al.; Bulletin de la Societe Chimique de France; (1966); p. 2653 - 2658, View in Reaxys 18 of 27

Melting Point [°C]

79 - 80

Solvent (Melting Point)

aq. ethanol

Goszczynski; Zeszyty Naukowe Politechniki Slaskiej, Chemia; vol. 25; (1964); p. 1,21,93; Chem.Abstr.; vol. 63; nb. 4253, View in Reaxys 19 of 27

Melting Point [°C]

80.5 - 81

Solvent (Melting Point)

ethanol

Wehrmeister; Journal of Organic Chemistry; vol. 27; (1962); p. 4418, View in Reaxys

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20 of 27

Melting Point [°C]

73.5

Solvent (Melting Point)

petroleum ether

Urushibara; Hirota; Nippon Kagaku Zasshi; vol. 82; (1961); p. 351,360; Chem.Abstr.; vol. 56; nb. 10025; (1962), View in Reaxys 21 of 27

Melting Point [°C]

Solvent (Melting Point)

petroleum ether; benzene

Urushibara; Hirota; Nippon Kagaku Zasshi; vol. 82; (1961); p. 351,360; Chem.Abstr.; vol. 56; nb. 10025; (1962), View in Reaxys 22 of 27

Melting Point [°C]

Solvent (Melting Point)

petroleum ether

Psarrea et al.; Bulletin de la Societe Chimique de France; (1961); p. 2152, View in Reaxys 23 of 27

Melting Point [°C]

Urushibara; Hirota; Nippon Kagaku Zasshi; vol. 82; (1961); p. 351,360; Chem.Abstr.; vol. 56; nb. 10025; (1962), View in Reaxys 24 of 27

Melting Point [°C]

81 - 81.2

Solvent (Melting Point)

ethanol

Jur'ew et al.; Zhurnal Obshchei Khimii; vol. 28; (1958); p. 1302,1305; engl. Ausg. S. 1361, 1363, View in Reaxys 25 of 27

Melting Point [°C]

82 - 83

Solvent (Melting Point)

H2O

Holden; Lapworth; Journal of the Chemical Society; (1931); p. 2368,2375, View in Reaxys; Johnson; Heinz; Journal of the American Chemical Society; vol. 71; (1949); p. 2913,2914, 2915, 4167, View in Reaxys 26 of 27

Melting Point [°C]

82 - 83

Solvent (Melting Point)

diethyl ether; petroleum ether

Melting Point [°C]

74 - 75

Solvent (Melting Point)

petroleum ether

Farmer; Hose; Journal of the Chemical Society; (1933); p. 962,965, View in Reaxys Boiling Point (1) Boiling Point [°C] 190

Pressure (Boiling Point) [Torr]

References

Auwers; Eisenlohr; Journal fuer Praktische Chemie (Leipzig); vol. <2> 84; (1911); p. 70, View in Reaxys

Density (1) 1 of 1

Density [g·cm-3]

1.24

Type (Density)

crystallographic

Bryan; White; Acta Crystallographica; vol. <B> 38; (1982); p. 1332, View in Reaxys; Bryan, Robert F.; White, Deborah H.; Acta Crystallographica, Section B: Structural Crystallography and Crystal Chemistry; vol. 38; (1982); p. 1332 - 1334, View in Reaxys Chromatographic Data (2) Chromatographic Location data

References

TLC (Thin layer chromatography)

Song, Cai-Xia; Chen, Ping; Tang, Yu; RSC Advances; vol. 7; nb. 19; (2017); p. 11233 - 11243, View in Reaxys

HPLC (High performance liquid chromatography)

supporting informa- Zirakzadeh, Afrooz; Gross, Manuela A.; Wang, Yaping; Mereiter, Kurt; Spindler, Felix; tion Weissensteiner, Walter; Organometallics; vol. 32; nb. 4; (2013); p. 1075 - 1084, View in Reaxys

Crystal Phase (2) Description (Crystal Phase)

Comment (Crystal Phase)

References

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Crystal structure determination

Roentgen-Diagramm.

Crystal structure determination

α=120.9 grad, Bryan, Robert F.; White, Deborah H.; Acta Crystallographica, Section B: Structural Crystalloga=7.63 Angstroem, raphy and Crystal Chemistry; vol. 38; (1982); p. 1332 - 1334, View in Reaxys b=11.45 Angstroem, c=11.51 Angstroem, n=4.; Method of determination: Single Crystal X-ray Diffraction

Crystal Property Description (5) Colour & Other Location Properties white

Bryan; White; Acta Crystallographica; vol. <B> 38; (1982); p. 1332, View in Reaxys

References Song, Cai-Xia; Chen, Ping; Tang, Yu; RSC Advances; vol. 7; nb. 19; (2017); p. 11233 - 11243, View in Reaxys

brown

supporting informa- Kerwat, Dennis; Grätz, Stefan; Kretz, Julian; Seidel, Maria; Kunert, Maria; Weston, John tion B.; Süssmuth, Roderich D.; ChemMedChem; (2016); p. 1899 - 1903, View in Reaxys

white

supporting informa- Wang, Xueqiang; Nakajima, Masaki; Martin, Ruben; Journal of the American Chemical Socition ety; vol. 137; nb. 28; (2015); p. 8924 - 8927, View in Reaxys

colourless

Prismen

Farmer; Hose; Journal of the Chemical Society; (1933); p. 962,965, View in Reaxys

Crystal System (1) Crystal System References monoclinic

Dissociation Exponent (2) 1 of 2

Comment (Dissociation Exponent)

(k')

Sandris; Tetrahedron; vol. 24; (1968); p. 3583, View in Reaxys 2 of 2

Comment (Dissociation Exponent)

(pk')pK: 6.10 in 50percentig. wss. A. bei 25+-1grad

References

Kleene; Westheimer; Wheland; Journal of the American Chemical Society; vol. 63; (1941); p. 791, View in Reaxys

Further Information (2) Description (FurReferences ther Information) Further information Beamer; Lawson; Journal of Pharmaceutical Sciences; vol. 55; (1966); p. 53,55, View in Reaxys Further information Psarrea et al.; Bulletin de la Societe Chimique de France; (1961); p. 2152, View in Reaxys Interatomic Distances and Angles (2) Description Comment (Interatomic Distances and Angles) Interatomic distances and angles

Roentgen-Diagramm.

Interatomic distances and angles

References

Bryan; White; Acta Crystallographica; vol. <B> 38; (1982); p. 1332, View in Reaxys Bryan, Robert F.; White, Deborah H.; Acta Crystallographica, Section B: Structural Crystallography and Crystal Chemistry; vol. 38; (1982); p. 1332 - 1334, View in Reaxys

Other Thermochemical Data (1)

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Description (Other Thermochemical Data)

Comment (Other Thermochemical Data)

Heat of combustion 1198.6 kcal/Mol. at constant volume Space Group (1) Space Group 14

References

Roth; v. Auwers; in Landolt-Boernst. H, 1605, View in Reaxys

References Bryan, Robert F.; White, Deborah H.; Acta Crystallographica, Section B: Structural Crystallography and Crystal Chemistry; vol. 38; (1982); p. 1332 - 1334, View in Reaxys

NMR Spectroscopy (27) 1 of 27

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 400 scopy) [MHz] Location

supporting information

Hou, Jing; Ee, Aloysius; Feng, Wei; Xu, Jin-Hui; Zhao, Yu; Wu, Jie; Journal of the American Chemical Society; vol. 140; nb. 15; (2018); p. 5257 - 5263, View in Reaxys 2 of 27

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectroscopy)

dimethylsulfoxide-d6

Frequency (NMR Spectro- 600 scopy) [MHz] Song, Cai-Xia; Chen, Ping; Tang, Yu; RSC Advances; vol. 7; nb. 19; (2017); p. 11233 - 11243, View in Reaxys 3 of 27

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

dimethylsulfoxide-d6

Frequency (NMR Spectro- 150 scopy) [MHz] Song, Cai-Xia; Chen, Ping; Tang, Yu; RSC Advances; vol. 7; nb. 19; (2017); p. 11233 - 11243, View in Reaxys 4 of 27

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectroscopy)

dimethylsulfoxide-d6

Frequency (NMR Spectro- 400 scopy) [MHz] Location

supporting information

Kerwat, Dennis; Grätz, Stefan; Kretz, Julian; Seidel, Maria; Kunert, Maria; Weston, John B.; Süssmuth, Roderich D.; ChemMedChem; (2016); p. 1899 - 1903, View in Reaxys 5 of 27

Description (NMR Spectroscopy)

Chemical shifts

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Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

dimethylsulfoxide-d6

Frequency (NMR Spectro- 100 scopy) [MHz] Location

supporting information

Kerwat, Dennis; Grätz, Stefan; Kretz, Julian; Seidel, Maria; Kunert, Maria; Weston, John B.; Süssmuth, Roderich D.; ChemMedChem; (2016); p. 1899 - 1903, View in Reaxys 6 of 27

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 500 scopy) [MHz] Location

supporting information

Wang, Xueqiang; Nakajima, Masaki; Martin, Ruben; Journal of the American Chemical Society; vol. 137; nb. 28; (2015); p. 8924 - 8927, View in Reaxys 7 of 27

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 126 scopy) [MHz] Location

supporting information

Wang, Xueqiang; Nakajima, Masaki; Martin, Ruben; Journal of the American Chemical Society; vol. 137; nb. 28; (2015); p. 8924 - 8927, View in Reaxys 8 of 27

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 400 scopy) [MHz] Location

supporting information

Beesu, Mallesh; Periasamy, Mariappan; Journal of Organometallic Chemistry; vol. 705; (2012); p. 30 - 33, View in Reaxys 9 of 27

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 100 scopy) [MHz] Location

supporting information

Beesu, Mallesh; Periasamy, Mariappan; Journal of Organometallic Chemistry; vol. 705; (2012); p. 30 - 33, View in Reaxys

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10 of 27

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 400 scopy) [MHz] Abe, Masato; Nishikawa, Keisuke; Okuda, Katsuhiro; Shindo, Mitsuru; Fukuda, Hiroshi; Nakanishi, Kazunari; Tazawa, Yuta; Taniguchi, Tomoya; Park, So-Young; Hiradate, Syuntaro; Fujii, Yoshiharu; Phytochemistry (Elsevier); vol. 84; (2012); p. 56 - 67,12, View in Reaxys 11 of 27

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 100 scopy) [MHz] Abe, Masato; Nishikawa, Keisuke; Okuda, Katsuhiro; Shindo, Mitsuru; Fukuda, Hiroshi; Nakanishi, Kazunari; Tazawa, Yuta; Taniguchi, Tomoya; Park, So-Young; Hiradate, Syuntaro; Fujii, Yoshiharu; Phytochemistry (Elsevier); vol. 84; (2012); p. 56 - 67,12, View in Reaxys 12 of 27

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 400 scopy) [MHz] Location

supporting information

Fujihara, Tetsuaki; Xu, Tinghua; Semba, Kazuhiko; Terao, Jun; Tsuji, Yasushi; Angewandte Chemie - International Edition; vol. 50; nb. 2; (2011); p. 523 - 527, View in Reaxys 13 of 27

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 100 scopy) [MHz] Location

supporting information

Fujihara, Tetsuaki; Xu, Tinghua; Semba, Kazuhiko; Terao, Jun; Tsuji, Yasushi; Angewandte Chemie - International Edition; vol. 50; nb. 2; (2011); p. 523 - 527, View in Reaxys 14 of 27

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectroscopy)

chloroform-d1; dimethylsulfoxide-d6

Frequency (NMR Spectro- 300 scopy) [MHz]

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An, Gwangil; Ahn, Hyunseok; De Castro, Kathlia A.; Rhee, Hakjune; Synthesis; nb. 3; (2010); p. 477 - 485; Art.No: F19009SS, View in Reaxys 15 of 27

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

CDCl3

Cristau; Taillefer; Tetrahedron; vol. 54; nb. 8; (1998); p. 1507 - 1522, View in Reaxys; Feuillet, Fred J. P.; Cheeseman, Matt; Mahon, Mary F.; Bull, Steven D.; Organic and Biomolecular Chemistry; vol. 3; nb. 16; (2005); p. 2976 - 2989, View in Reaxys 16 of 27

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectroscopy)

CDCl3

Frequency (NMR Spectro- 300 scopy) [MHz] Feuillet, Fred J. P.; Robinson, Diane E. J. E.; Bull, Steven D.; Chemical Communications; nb. 17; (2003); p. 2184 - 2185, View in Reaxys; Feuillet, Fred J. P.; Cheeseman, Matt; Mahon, Mary F.; Bull, Steven D.; Organic and Biomolecular Chemistry; vol. 3; nb. 16; (2005); p. 2976 - 2989, View in Reaxys 17 of 27

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

CDCl3

Frequency (NMR Spectro- 75 scopy) [MHz] Feuillet, Fred J. P.; Robinson, Diane E. J. E.; Bull, Steven D.; Chemical Communications; nb. 17; (2003); p. 2184 - 2185, View in Reaxys 18 of 27

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectroscopy)

CDCl3

Frequency (NMR Spectro- 400 scopy) [MHz] Rudler, Henri; Durand-Reville, Thomas; Journal of Organometallic Chemistry; vol. 617; nb. 1; (2001); p. 571 - 587, View in Reaxys 19 of 27

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectroscopy)

CDCl3

Frequency (NMR Spectro- 400 scopy) [MHz] Rudler, Henri; Durand-Reville, Thomas; Journal of Organometallic Chemistry; vol. 617; nb. 1; (2001); p. 571 - 587, View in Reaxys 20 of 27

Description (NMR Spectroscopy)

Chemical shifts

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Nucleus (NMR Spectroscopy)

Basavaiah; Krishnamacharyulu; Hyma; Sarma; Kumaragurubaran; Journal of Organic Chemistry; vol. 64; nb. 4; (1999); p. 1197 - 1200, View in Reaxys 21 of 27

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

13C

Basavaiah; Krishnamacharyulu; Hyma; Sarma; Kumaragurubaran; Journal of Organic Chemistry; vol. 64; nb. 4; (1999); p. 1197 - 1200, View in Reaxys 22 of 27

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectroscopy)

CDCl3

Brittelli, David R.; Journal of Organic Chemistry; vol. 46; nb. 12; (1981); p. 2514 - 2520, View in Reaxys; Dalcanale, Enrico; Montanari, Fernando; Journal of Organic Chemistry; vol. 51; nb. 4; (1986); p. 567 - 569, View in Reaxys; Robert; RobertPiessard; Duflos; Le Baut; Khettab; Grimaud; Petit; Welin; European Journal of Medicinal Chemistry; vol. 29; nb. 11; (1994); p. 841 - 854, View in Reaxys; Cristau; Taillefer; Tetrahedron; vol. 54; nb. 8; (1998); p. 1507 - 1522, View in Reaxys; Stratakis, Manolis; Orfanopoulos, Michael; Foote, Christopher S.; Journal of Organic Chemistry; vol. 63; nb. 4; (1998); p. 1315 - 1318, View in Reaxys 23 of 27

Description (NMR Spectroscopy)

Spin-spin coupling constants

Solvents (NMR Spectroscopy)

CDCl3

Comment (NMR Spectroscopy)

1H-1H

Brittelli, David R.; Journal of Organic Chemistry; vol. 46; nb. 12; (1981); p. 2514 - 2520, View in Reaxys; Robert; RobertPiessard; Duflos; Le Baut; Khettab; Grimaud; Petit; Welin; European Journal of Medicinal Chemistry; vol. 29; nb. 11; (1994); p. 841 - 854, View in Reaxys; Cristau; Taillefer; Tetrahedron; vol. 54; nb. 8; (1998); p. 1507 - 1522, View in Reaxys; Stratakis, Manolis; Orfanopoulos, Michael; Foote, Christopher S.; Journal of Organic Chemistry; vol. 63; nb. 4; (1998); p. 1315 - 1318, View in Reaxys 24 of 27

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

dimethylsulfoxide-d6

Teulade, Marie-Paule; Savignac, Philippe; About-Jaudet, Elie; Collignon, Nooel; Synthetic Communications; vol. 19; nb. 1, 2; (1989); p. 71 - 82, View in Reaxys 25 of 27

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectroscopy)

CHCl3

Somasekharan, K. N.; Kiefer, Edgar F.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 27; nb. 1-12; (1988); p. 29 - 37, View in Reaxys 26 of 27

Description (NMR Spectroscopy)

Spin-spin coupling constants

Solvents (NMR Spectroscopy)

CHCl3

Comment (NMR Spectroscopy)

1H-1H.

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Somasekharan, K. N.; Kiefer, Edgar F.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 27; nb. 1-12; (1988); p. 29 - 37, View in Reaxys 27 of 27

Description (NMR Spectroscopy)

NMR

Dzurilla,M. et al.; Collection of Czechoslovak Chemical Communications; vol. 42; (1977); p. 2938 - 2944, View in Reaxys; Bisson,R. et al.; Canadian Journal of Chemistry; vol. 50; (1972); p. 2851 - 2858, View in Reaxys; Julia,M.; Binet du Jassonneix,C.; Bulletin de la Societe Chimique de France; (1975); p. 743 - 750, View in Reaxys; Klein; Levene; Journal of the American Chemical Society; vol. 94; (1972); p. 2520, View in Reaxys; Bright et al.; Journal of Organic Chemistry; vol. 38; (1973); p. 2554, View in Reaxys; Singer; Kong; Journal of the American Chemical Society; vol. 88; (1966); p. 5213,5214, View in Reaxys IR Spectroscopy (6) 1 of 6

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat liquid

Feuillet, Fred J. P.; Cheeseman, Matt; Mahon, Mary F.; Bull, Steven D.; Organic and Biomolecular Chemistry; vol. 3; nb. 16; (2005); p. 2976 - 2989, View in Reaxys 3 of 6

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

3350 - 1620 1/cm

Basavaiah; Krishnamacharyulu; Hyma; Sarma; Kumaragurubaran; Journal of Organic Chemistry; vol. 64; nb. 4; (1999); p. 1197 - 1200, View in Reaxys 4 of 6

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

3425 - 680 cm**(-1)

Cristau; Taillefer; Tetrahedron; vol. 54; nb. 8; (1998); p. 1507 - 1522, View in Reaxys 5 of 6

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

CHCl3

Comment (IR Spectroscopy)

3600 - 1650 cm**(-1)

Brittelli, David R.; Journal of Organic Chemistry; vol. 46; nb. 12; (1981); p. 2514 - 2520, View in Reaxys 6 of 6

Description (IR Spectroscopy)

Bisson,R. et al.; Canadian Journal of Chemistry; vol. 50; (1972); p. 2851 - 2858, View in Reaxys; Julia,M.; Binet du Jassonneix,C.; Bulletin de la Societe Chimique de France; (1975); p. 743 - 750, View in Reaxys Mass Spectrometry (6) Description (Mass Location Spectrometry)

References

electrospray ionisation (ESI); spectrum

Song, Cai-Xia; Chen, Ping; Tang, Yu; RSC Advances; vol. 7; nb. 19; (2017); p. 11233 - 11243, View in Reaxys

high resolution mass spectrometry (HRMS); electro-

Song, Cai-Xia; Chen, Ping; Tang, Yu; RSC Advances; vol. 7; nb. 19; (2017); p. 11233 - 11243, View in Reaxys

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spray ionisation (ESI); spectrum electrospray ionisa- supporting informa- Kerwat, Dennis; Grätz, Stefan; Kretz, Julian; Seidel, Maria; Kunert, Maria; Weston, John tion (ESI); high res- tion B.; Süssmuth, Roderich D.; ChemMedChem; (2016); p. 1899 - 1903, View in Reaxys olution mass spectrometry (HRMS); spectrum electron impact (EI); spectrum

high resolution mass spectrometry (HRMS); electron impact (EI); spectrum

spectrum; electron impact (EI)

UV/VIS Spectroscopy (6) 1 of 6

Description (UV/VIS Spectroscopy)

UV/VIS

Description (UV/VIS Spectroscopy)

Absorption maxima

Psarrea et al.; Bulletin de la Societe Chimique de France; (1961); p. 2152, View in Reaxys; Urushibara; Hirota; Nippon Kagaku Zasshi; vol. 82; (1961); p. 351,360; Chem.Abstr.; vol. 56; nb. 10025; (1962), View in Reaxys 3 of 6

Description (UV/VIS Spectroscopy)

Absorption maxima

Solvent (UV/VIS Spectroscopy)

ethanol

Mangini; Montanari; Gazzetta Chimica Italiana; vol. 88; (1958); p. 1081,1088 Tab., View in Reaxys 4 of 6

Description (UV/VIS Spectroscopy)

Absorption maxima

Solvent (UV/VIS Spectroscopy)

aq. NaOH

Mangini; Montanari; Gazzetta Chimica Italiana; vol. 88; (1958); p. 1081,1088 Tab., View in Reaxys 5 of 6

Description (UV/VIS Spectroscopy)

Spectrum

Ramart-Lucas; Trivedi; Bulletin de la Societe Chimique de France; vol. <4> 53; (1933); p. 178,183, View in Reaxys 6 of 6

Description (UV/VIS Spectroscopy)

Spectrum

Solvent (UV/VIS Spectroscopy)

ethanol

Ley; Chemische Berichte; vol. 50; (1917); p. 244; Chem. Zentralbl.; vol. 90; nb. I; (1919); p. 947, View in Reaxys Medchem (12) 1 of 12

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Effect : |metabolic Bioassay : inhibition of anthocyanin production in illuminated buckwheat hypocotils determined

Biological Species/NCBI ID

wild buckwheat

Substance RN

2042546View in Reaxys

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Substance Name

1456032

Qualitative Results

inhibition of anthocyanin production ca. 70 percent

Measurement Parameter

qualitative

Kluczyk; Szefczyk; Amrhein; Zon; Polish Journal of Chemistry; vol. 79; nb. 3; (2005); p. 583 - 592, View in Reaxys 2 of 12

Target Name

Phenylalanine ammonia-lyase [wild buckwheat]

Target Synonyms

phenylalanine ammonia-lyase

Target, Subunit, Species

Phenylalanine ammonia-lyase [wild buckwheat]

Target Mutant/Chimera Details

Phenylalanine ammonia-lyase [wild buckwheat]:Wild

Target Species (Bioactivity)

wild buckwheat

Target Transfection

Non Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Effect : |enzyme; inhibition of

Substance RN

2042546View in Reaxys

Substance Name

1456032

Qualitative Results

phenylalanine ammonia-lyase inhibition ca. 52 percent

Measurement Parameter

qualitative

Kluczyk; Szefczyk; Amrhein; Zon; Polish Journal of Chemistry; vol. 79; nb. 3; (2005); p. 583 - 592, View in Reaxys 3 of 12

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Substance RN

2042546View in Reaxys

Substance Name

1456032

Qualitative Results

inhibitory activity (percent) against phenylalanine ammonia-lyase derived from: sweet potato 34, yeast 27

Measurement Parameter

qualitative

Sato, Toshitsugu; Kiuchi, Fumiyuki; Sankawa, Ushio; Phytochemistry (Elsevier); vol. 21; nb. 4; (1982); p. 845 - 850, View in Reaxys 4 of 12

Target Name

Aldo-keto reductase family 1 member C3 [human]

Target Synonyms

17-beta-hsd 5; 17-beta-hydroxysteroid dehydrogenase type 5; 3-alpha-hsd type 2; 3-alpha-hsd type ii, brain; 3-alpha-hydroxysteroid dehydrogenase type 2; akr1c3; aldo-keto reductase family 1 member c3; chlordecone reductase homolog hakrb; dd-3; dd3; ddh1; dihydrodiol dehydrogenase 3; dihydrodiol dehydrogenase type i; ha1753; hsd17b5; indanol dehydrogenase; kiaa0119; pgfs; prostaglandin f synthase; testosterone 17-beta-dehydrogenase 5; trans-1,2-dihydrobenzene-1,2-diol dehydrogenase

Target Uniprot ID

p42330

Target PDB ID

1ry0; 1ry8; 1s1p; 1s1r; 1s2a; 1s2c; 1xf0; 1zq5; 2f38; 2fgb; 3r43; 3r58; 3r6i; 3r7m; 3r8g; 3r8h; 3r94; 3ufy; 3ug8; 3ugr; 3uwe; 4dbs; 4dbu; 4dbw; 4dz5; 4fa3; 4fal; 4fam; 4h7c; 4hmn; 4wdt; 4wdu; 4wdw; 4wdx; 4wrh; 4xvd; 4xve; 4yvv; 4yvx; 4zfc; 5hnt; 5hnu; 5jm5

Target, Subunit, Species

Aldo-keto reductase family 1 member C3 [human]

Target Mutant/Chimera Details

Aldo-keto reductase family 1 member C3 [human]:Wild

Target Species (Bioactivity)

human

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory concentration of compound against human recombinant AKR1C3 was determined

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Biological Species/NCBI ID

5 of 12

6 of 12

human

Substance RN

2042546View in Reaxys

Measurement Parameter

IC50

Unit

µM

Qualitative value

Quantitative value

6.4

Measurement pX

5.19

Target Name

Aldo-keto reductase family 1 member C3 [human]

Target Synonyms

Target Uniprot ID

p42330

Target PDB ID

Target, Subunit, Species

Aldo-keto reductase family 1 member C3 [human]

Target Mutant/Chimera Details

Aldo-keto reductase family 1 member C3 [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory concentration of the compound against human recombinant 17beta-Hydroxysteroid dehydrogenase type 5 (AKR1C3) using 5 uM 9,10-phenanthrenequinone as substrate and 200 uM NADPH

Biological Species/NCBI ID

human

Substance RN

2042546View in Reaxys

Measurement Parameter

IC50

Unit

µM

Qualitative value

Quantitative value

6.4

Measurement pX

5.19

Concomitants: Compound name

10-phenanthrenequinone; 9; NADPH

Concomitants: Compound role

SUB; SUB; COM

Target Name

Aldo-keto reductase family 1 member C3

Target Synonyms

Target, Subunit, Species

Aldo-keto reductase family 1 member C3

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7 of 12

8 of 12

Target Mutant/Chimera Details

Aldo-keto reductase family 1 member C3:Wild

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory concentration of the compound against AKR1C3 was determined

Substance RN

2042546View in Reaxys

Measurement Parameter

IC50

Unit

µM

Qualitative value

Quantitative value

6.4

Measurement pX

5.19

Target Name

Aldo-keto reductase family 1 member C3

Target Synonyms

Target, Subunit, Species

Aldo-keto reductase family 1 member C3

Target Mutant/Chimera Details

Aldo-keto reductase family 1 member C3:Wild

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory concentration of compound against 9,10-phenanthrenequinone reduction catalyzed by AKR1C3

Substance RN

2042546View in Reaxys

Measurement Parameter

IC50

Unit

µM

Qualitative value

Quantitative value

6.4

Measurement pX

5.19

Concomitants: Compound name

10-PHENANTHRENEQUINONE; 9

Concomitants: Compound role

SUB; SUB

Target Name

Aldo-keto reductase family 1 member C3 [human]

Target Synonyms

Target Uniprot ID

p42330

Target PDB ID

Target, Subunit, Species

Aldo-keto reductase family 1 member C3 [human]

Target Mutant/Chimera Details

Aldo-keto reductase family 1 member C3 [human]:Wild

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10 of 12

Target Species (Bioactivity)

human

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro inhibitory concentration of the compound (dissolved in DMSO) against homogenous recombinant human AKR1C3 receptor using 165 uM S-tetralol as substrate upon incubation at 37 degree C in 100 mM phosphate buffer, pH 7.0 in presence of 200 uM NADP+

Biological Species/NCBI ID

human

Substance RN

2042546View in Reaxys

Measurement Parameter

IC50

Unit

ÂľM

Qualitative value

Quantitative value

6.4

Measurement pX

5.19

Concomitants: Compound name

NADP+; S-TETRALOL

Concomitants: Compound role

COM; SUB

Target Name

Aldo-keto reductase family 1 member C1 [human]

Target Synonyms

20-alpha-hsd; 20-alpha-hydroxysteroid dehydrogenase; akr1c1; aldo-keto reductase family 1 member c1; chlordecone reductase homolog hakrc; dd1/dd2; ddh; ddh1; dihydrodiol dehydrogenase 1/2; hbab; high-affinity hepatic bile acid-binding protein; indanol dehydrogenase; trans-1,2-dihydrobenzene-1,2-diol dehydrogenase

Target Uniprot ID

q04828

Target PDB ID

1mrq; 3c3u; 3gug; 3nty; 4yvp

Target, Subunit, Species

Aldo-keto reductase family 1 member C1 [human]

Target Mutant/Chimera Details

Aldo-keto reductase family 1 member C1 [human]:Wild

Target Species (Bioactivity)

human

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro inhibitory concentration of the compound (dissolved in DMSO) against homogenous recombinant human AKR1C1 receptor using S-tetralol as substrate upon incubation at 37 degree C in 100 mM phosphate buffer, pH 7.0 in presence of 200 uM NADP+

Biological Species/NCBI ID

human

Substance RN

2042546View in Reaxys

Qualitative Results

ND = Not determined

Measurement Parameter

qualitative

Measurement Object

IC50

Concomitants: Compound name

NADP+; S-TETRALOL

Concomitants: Compound role

COM; SUB

Target Name

Aldo-keto reductase family 1 member C2 [human]

Target Synonyms

3-alpha-hsd3; akr1c2; aldo-keto reductase family 1 member c2; chlordecone reductase homolog hakrd; dd-2; dd/babp; dd2; ddh2; dihydrodiol dehydrogenase 2; dihydrodiol dehydrogenase/bile acid-binding protein; trans-1,2-dihydrobenzene-1,2-diol dehydrogenase; type iii 3-alpha-hydroxysteroid dehydrogenase

Target Uniprot ID

p52895

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11 of 12

Target PDB ID

1ihi; 1j96; 1xjb; 2hdj; 2ipj; 4jq1; 4jq2; 4jq3; 4jq4; 4jqa; 4jtq; 4jtr; 4l1w; 4l1x; 4xo6; 4xo7

Target, Subunit, Species

Aldo-keto reductase family 1 member C2 [human]

Target Mutant/Chimera Details

Aldo-keto reductase family 1 member C2 [human]:Wild

Target Species (Bioactivity)

human

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro inhibitory concentration of the compound (dissolved in DMSO) against homogenous recombinant human AKR1C2 receptor using 22.5 uM S-tetralol as substrate upon incubation at 37 degree C in 100 mM phosphate buffer, pH 7.0 in presence of 200 uM NADP+

Biological Species/NCBI ID

human

Substance RN

2042546View in Reaxys

Qualitative Results

ND = Not determined

Measurement Parameter

qualitative

Measurement Object

IC50

Concomitants: Compound name

NADP+; S-TETRALOL

Concomitants: Compound role

COM; SUB

Substance Effect

Antifungal

Bioassay Category

In Vitro (Efficacy)

Biological Species/NCBI ID

Aspergillus fumigatus

Substance RN

2042546View in Reaxys

Substance Name

methylcinnamic acid

Measurement Parameter

inhibition rate

Qualitative value

Active

Patent; University College Cork-National University of Ireland, Cork; ARENDT, Elke K; DAL BELLO, Fabio; RYAN, Liam; EP2282639; (2014); (B1) English, View in Reaxys 12 of 12

Target Name

Aldo-keto reductase family 1 member C3 [human]

Target Synonyms

Target Uniprot ID

p42330

Target PDB ID

Target, Subunit, Species

Aldo-keto reductase family 1 member C3 [human]

Target Mutant/Chimera Details

Aldo-keto reductase family 1 member C3 [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

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Substance RN

2042546View in Reaxys

Substance Name

α-methylcinnamic acid

Measurement Parameter

IC50

Unit

μM

Quantitative value

6.4

Measurement pX

5.19

Concomitants: Compound RN

2208779

Concomitants: Compound name

S-tetralol

Concomitants: Compound role

SUB

Reaxys ID 5172722 View in Reaxys

4/5 CAS Registry Number: 79044-44-3 Chemical Name: sodium (E)-2-methyl-3-phenylacrylate; Natrium(E)-2-methylcinnamat; 2-methyl-3t-phenyl-acrylic acid ; sodium salt; 2-Methyl-3t-phenyl-acrylsaeure; Natriumsalz Linear Structure Formula: C10H9O2 (1-)*Na(1+) Molecular Formula: C10H9O2*Na Molecular Weight: 184.17 Type of Substance: isocyclic InChI Key: FRCPDSPQDRUUAA-USRGLUTNSA-M Note:

O–

Na +

Druglikeness (1) 1 of 1

LogP

1.609

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

40.13

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

280

Vorlaender; Chemische Berichte; vol. 43; (1910); p. 3122,3132, View in Reaxys

Reaxys ID 6098658 View in Reaxys

5/5 CAS Registry Number: 136819-51-7 Chemical Name: 2-methyl-3t-phenyl-acrylic acid ; potassium salt; 2Methyl-3t-phenyl-acrylsaeure; Kaliumsalz Linear Structure Formula: C10H9O2 (1-)*K(1+) Molecular Formula: C10H9O2*K Molecular Weight: 200.279 Type of Substance: isocyclic InChI Key: YKVFMSYVFRAYFL-USRGLUTNSA-M

O–

K+

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Note: Druglikeness (1) 1 of 1

LogP

1.609

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

40.13

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [Â°C]

310

Vorlaender; Chemische Berichte; vol. 43; (1910); p. 3122,3132, View in Reaxys

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