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2 substances in Reaxys
2018-02-09 04h:27m:17s (EST)
O
1. Query O
Search as: As drawn
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Reaxys ID 135375 View in Reaxys
Cl
1/2 CAS Registry Number: 20850-43-5 Chemical Name: 5-(chloromethyl)-1,3-benzodioxole; 3,4-methylenedioxybenzyl chloride; 3,4-Methylenedioxybenzyl chloride Linear Structure Formula: C8H7ClO2 Molecular Formula: C8H7ClO2 Molecular Weight: 170.595 Type of Substance: heterocyclic InChI Key: DWSUJONSJJTODA-UHFFFAOYSA-N Note:
O O
Substance Label (22) Label References 1i
Yuan, Gengyang; Wang, Feng; Stephenson, Nickeisha A.; Wang, Lu; Rotstein, Benjamin H.; Vasdev, Neil; Tang, Pingping; Liang, Steven H.; Chemical Communications; vol. 53; nb. 1; (2017); p. 126 - 129, View in Reaxys
10a
Park, Hye-Kyung; Jeong, Hanbin; Ko, Eunhwa; Lee, Geumwoo; Lee, Ji-Eun; Lee, Sang Kwang; Lee, An-Jung; Im, Jin Young; Hu, Sung; Kim, Seong Heon; Lee, Ji Hoon; Lee, Changwook; Kang, Soosung; Kang, Byoung Heon; Journal of Medicinal Chemistry; vol. 60; nb. 17; (2017); p. 7569 - 7578, View in Reaxys
6a
Ellwart, Mario; Höfner, Georg; Gerwien, Aaron; Wanner, Klaus T.; Knochel, Paul; Synthesis (Germany); vol. 49; nb. 23; (2017); p. 5159 - 5166, View in Reaxys
X
Patent; ANTHEA AROMATICS PRIVATE LIMITED; MOHAPATRA, Manoj Kumar; BENDAPUDI, Ramamohanrao; MENACHERRY, Paul Vincent; PAUL, Vincent; (31 pag.); WO2016/103058; (2016); (A1) English, View in Reaxys
2e
Cai, Jin; Liu, Ligang; Hong, Kwon Ho; Wang, Peng; Li, Lushen; Cao, Meng; Sun, Chunlong; Wu, Xiaoqing; Zong, Xi; Chen, Junqing; Ji, Min; Bioorganic and Medicinal Chemistry; vol. 23; nb. 4; (2015); p. 657 - 667, View in Reaxys
2
Zhang, Bingyu; Lv, Chao; Li, Weibo; Cui, Zhiming; Chen, Dongdong; Cao, Fangjun; Miao, Fang; Zhou, Le; Chemical and Pharmaceutical Bulletin; vol. 63; nb. 4; (2015); p. 255 - 262, View in Reaxys
7
Marguerit, Melanie; Little, Gill; Wang, Yi; He, Linli; Allwein, Shawn; Reif, James; Rossi, Jason; Roemmele, Renee; Bakale, Roger; European Journal of Organic Chemistry; vol. 2015; nb. 36; (2015); p. 8003 8010, View in Reaxys
9i
Liao, Yung-Feng; Tang, Yu-Cheng; Chang, Ming-Yun; Wang, Bo-Jeng; Hu, Ming-Kuan; European Journal of Medicinal Chemistry; vol. 79; (2014); p. 143 - 151, View in Reaxys
1c
Miyake, Yoshihiro; Ota, Shin-Ichi; Shibata, Masashi; Nakajima, Kazunari; Nishibayashi, Yoshiaki; Organic and Biomolecular Chemistry; vol. 12; nb. 30; (2014); p. 5594 - 5596, View in Reaxys
173.2
Patent; Nimbus Apollo, Inc.; Harriman, Geraldine C.; Masse, Craig E.; Harwood, James; Bhat, Sathesh; Greenwood, Jeremy Robert; US2013/123231; (2013); (A1) English, View in Reaxys
1-1
Wei, Meng-Xue; Wang, Cheng-Tao; Du, Ji-Yuan; Qu, Hu; Yin, Pei-Rong; Bao, Xu; Ma, Xiao-Yan; Zhao, Xian-He; Zhang, Guo-Biao; Fan, Chun-An; Chemistry - An Asian Journal; vol. 8; nb. 9; (2013); p. 1966 1971, View in Reaxys
compound 18
Patent; H. Lundbeck A/S; US2009/62324; (2009); (A1) English, View in Reaxys; Patent; H. LUNDBECK A/S; WO2009/26934; (2009); (A1) English, View in Reaxys
15
Porcal, Williams; Merlino, Alicia; Boiani, Mariana; Gerpe, Alejandra; Gonzalez, Mercedes; Cerecetto, Hugo; Organic Process Research and Development; vol. 12; nb. 2; (2008); p. 156 - 162, View in Reaxys
10
Westermaier, Martin; Mayr, Herbert; Organic Letters; vol. 8; nb. 21; (2006); p. 4791 - 4794, View in Reaxys
18
Peng, Yu; Li, Wei-Dong Z.; Synlett; nb. 8; (2006); p. 1165 - 1168, View in Reaxys
17
Fujioka, Hiromichi; Murai, Kenichi; Ohba, Yusuke; Hirose, Hideki; Kita, Yasuyuki; Chemical Communications; nb. 8; (2006); p. 832 - 834, View in Reaxys
20
Klein, Thomas A.; Schkeryantz, Jeffrey M.; Tetrahedron Letters; vol. 46; nb. 27; (2005); p. 4535 - 4538, View in Reaxys
Chemical Formula 3
Patent; HAN, Sang Min; LEE, Myung Hee; CHOI, Won Chul; WO2005/70915; (2005); (A1) English, View in Reaxys
1b
Bie, Pingyan; Zhang, Chenglu; Peng, Xuanjia; Chen, Bo; Wu, Tongxing; Pan, Xinfu; Journal of Chemical Research - Part S; nb. 4; (2003); p. 211 - 213, View in Reaxys
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int. to Me-ester of 2b
Bourry, Anne; Akue-Gedu, Rufine; Rigo, Benoit; Henichart, Jean-Pierre; Sanz, Gerard; Couturier, Daniel; Journal of Heterocyclic Chemistry; vol. 40; nb. 6; (2003); p. 989 - 993, View in Reaxys
34a
Zhang, Jidong; Didierlaurent, Stanislas; Fortin, Michel; Lefrancois, Dominique; Uridat, Eric; Vevert, Jean Paul; Bioorganic and Medicinal Chemistry Letters; vol. 10; nb. 12; (2000); p. 1351 - 1355, View in Reaxys
8a
Berger, Dan; Citarella, Ron; Dutia, Minu; Greenberger, Lee; Hallett, William; Paul, Rolf; Powell, Dennis; Journal of Medicinal Chemistry; vol. 42; nb. 12; (1999); p. 2145 - 2161, View in Reaxys
Patent-Specific Data (7) Location in Patent References Claim
Patent; Farmaceutici Geymonat Sud S.P.A.; US4264770; (1981); (A1) English, View in Reaxys; Patent; Doi, Takashi; Yoshida, Yoshihiro; Douyama, Daisuke; Katsura, Ryousuke; Fujitsu, Satoru; Yasuda, Shinji; Kimura, Keisuke; Oomori, Kiyoshi; US2012/323021; (2012); (A1) English, View in Reaxys Patent; GHARDA, Keki Hormusji; US2012/296119; (2012); (A1) English, View in Reaxys Patent; Doi, Takashi; Yoshida, Yoshihiro; Douyama, Daisuke; Katsura, Ryousuke; Fujitsu, Satoru; Yasuda, Shinji; Kimura, Keisuke; Oomori, Kiyoshi; US2012/323021; (2012); (A1) English, View in Reaxys Patent; GHARDA, Keki Hormusji; WO2011/80752; (2011); (A1) English, View in Reaxys Patent; JANSSEN PHARMACEUTICA NV; WO2008/90200; (2008); (A2) English, View in Reaxys Patent; ENDURA S.P.A.; WO2005/42512; (2005); (A1) English, View in Reaxys Patent; PHARMACIA and UPJOHN COMPANY; EP1247804; (2002); (A1) English, View in Reaxys
Druglikeness (1) 1 of 1
LogP
1.974
H Bond Donors
0
H Bond Acceptors
0
Rotatable Bonds
1
TPSA
18.46
Lipinski Number
4
Veber Number
2
Melting Point (6) 1 of 6
Melting Point [°C]
23 - 24
Cai, Jin; Liu, Ligang; Hong, Kwon Ho; Wang, Peng; Li, Lushen; Cao, Meng; Sun, Chunlong; Wu, Xiaoqing; Zong, Xi; Chen, Junqing; Ji, Min; Bioorganic and Medicinal Chemistry; vol. 23; nb. 4; (2015); p. 657 - 667, View in Reaxys 2 of 6
Melting Point [°C]
20
Solvent (Melting Point)
benzene
Yamada et al.; Chemical and Pharmaceutical Bulletin; vol. 10; (1962); p. 680,684, View in Reaxys 3 of 6
Melting Point [°C]
23 - 23.5
Baddeley et al.; Journal of the Chemical Society; (1961); p. 2516,2517, View in Reaxys 4 of 6
Melting Point [°C]
20 - 21
Schorygin et al.; Zhurnal Obshchei Khimii; vol. 8; (1938); p. 975,978; Chem. Zentralbl.; vol. 110; nb. I; (1939); p. 2178, View in Reaxys 5 of 6
Melting Point [°C]
23
Solvent (Melting Point)
ethanol
Tiffeneau; Bulletin de la Societe Chimique de France; vol. <4> 9; (1911); p. 932, View in Reaxys 6 of 6
Melting Point [°C]
23
Decker; Koch; Chemische Berichte; vol. 38; (1905); p. 1741, View in Reaxys Boiling Point (9) Boiling Point [°C]
Pressure (Boiling Point) [Torr]
References
Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
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130 - 135
13
Vinogradova, V. I.; Yunusov, M. S.; Kuchin, A. V.; Tolstikov, G. A.; Sagandykov, R. T.; et al.; Chemistry of Natural Compounds; vol. 26; nb. 1; (1990); p. 54 - 59; Khimiya Prirodnykh Soedinenii; nb. 1; (1990); p. 67 - 74, View in Reaxys
78 - 80
0.05
Gensler,W.J. et al.; Journal of Organic Chemistry; vol. 40; (1975); p. 733 - 739, View in Reaxys
91 - 94
2
Birch,A.J. et al.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1974); p. 2190 - 2194, View in Reaxys
88 - 91
3.5
Dallacker,F. et al.; Chemische Berichte; vol. 104; (1971); p. 2526 - 2533, View in Reaxys
129
13
Matsumoto; Chemical and pharmaceutical bulletin; vol. 15; nb. 12; (1967); p. 1990 1995, View in Reaxys
89 - 91
1
Spaeth; Schmidt; Monatshefte fuer Chemie; vol. 53/54; (1929); p. 469, View in Reaxys
126
15
Mannich; Walther; Archiv der Pharmazie (Weinheim, Germany); (1927); p. 7, View in Reaxys
130 - 131
13
Tiffeneau; Bulletin de la Societe Chimique de France; vol. <4> 9; (1911); p. 932, View in Reaxys
134 - 135
14
Ewins; Journal of the Chemical Society; vol. 95; (1909); p. 1485, View in Reaxys
Chromatographic Data (1) Chromatographic References data TLC (Thin layer chromatography)
Porcal, Williams; Merlino, Alicia; Boiani, Mariana; Gerpe, Alejandra; Gonzalez, Mercedes; Cerecetto, Hugo; Organic Process Research and Development; vol. 12; nb. 2; (2008); p. 156 - 162, View in Reaxys
Crystal Property Description (6) Colour & Other Location Properties colourless
References Cai, Jin; Liu, Ligang; Hong, Kwon Ho; Wang, Peng; Li, Lushen; Cao, Meng; Sun, Chunlong; Wu, Xiaoqing; Zong, Xi; Chen, Junqing; Ji, Min; Bioorganic and Medicinal Chemistry; vol. 23; nb. 4; (2015); p. 657 - 667, View in Reaxys
green
supporting information
Marguerit, Melanie; Little, Gill; Wang, Yi; He, Linli; Allwein, Shawn; Reif, James; Rossi, Jason; Roemmele, Renee; Bakale, Roger; European Journal of Organic Chemistry; vol. 2015; nb. 36; (2015); p. 8003 - 8010, View in Reaxys
colourless
supporting information
Sun, Yan-Yan; Yi, Jun; Lu, Xi; Zhang, Zhen-Qi; Xiao, Bin; Fu, Yao; Chemical Communications; vol. 50; nb. 75; (2014); p. 11060 - 11062, View in Reaxys
yellow
Paragraph 1301
Patent; Nimbus Apollo, Inc.; Harriman, Geraldine C.; Masse, Craig E.; Harwood, James; Bhat, Sathesh; Greenwood, Jeremy Robert; US2013/123231; (2013); (A1) English, View in Reaxys
yellow
Porcal, Williams; Merlino, Alicia; Boiani, Mariana; Gerpe, Alejandra; Gonzalez, Mercedes; Cerecetto, Hugo; Organic Process Research and Development; vol. 12; nb. 2; (2008); p. 156 - 162, View in Reaxys
Nadeln
Decker; Koch; Chemische Berichte; vol. 38; (1905); p. 1741, View in Reaxys
Other Thermochemical Data (1) Description (Oth- References er Thermochemical Data) Thermodynamic properties
Baddeley et al.; Journal of the Chemical Society; (1961); p. 2516,2517, View in Reaxys
NMR Spectroscopy (11) 1 of 11
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
300
Location
Paragraph 0291
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Patent; Korea Institute of Science and Technology; Kum, Kyo Chang; Kim, Eun Kyung; Sau, Sun Hee; Lee, Jae Wook; Lee, Joo Hyun; Sin, Sang Chul; (39 pag.); KR2016/59366; (2016); (A) Korean, View in Reaxys 2 of 11
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
75
Location
Paragraph 0292
Patent; Korea Institute of Science and Technology; Kum, Kyo Chang; Kim, Eun Kyung; Sau, Sun Hee; Lee, Jae Wook; Lee, Joo Hyun; Sin, Sang Chul; (39 pag.); KR2016/59366; (2016); (A) Korean, View in Reaxys 3 of 11
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
300
Location
supporting information
Marguerit, Melanie; Little, Gill; Wang, Yi; He, Linli; Allwein, Shawn; Reif, James; Rossi, Jason; Roemmele, Renee; Bakale, Roger; European Journal of Organic Chemistry; vol. 2015; nb. 36; (2015); p. 8003 - 8010, View in Reaxys 4 of 11
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
400
Location
supporting information
Sun, Yan-Yan; Yi, Jun; Lu, Xi; Zhang, Zhen-Qi; Xiao, Bin; Fu, Yao; Chemical Communications; vol. 50; nb. 75; (2014); p. 11060 - 11062, View in Reaxys 5 of 11
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
101
Location
supporting information
Sun, Yan-Yan; Yi, Jun; Lu, Xi; Zhang, Zhen-Qi; Xiao, Bin; Fu, Yao; Chemical Communications; vol. 50; nb. 75; (2014); p. 11060 - 11062, View in Reaxys 6 of 11
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
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Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
400.1
Porcal, Williams; Merlino, Alicia; Boiani, Mariana; Gerpe, Alejandra; Gonzalez, Mercedes; Cerecetto, Hugo; Organic Process Research and Development; vol. 12; nb. 2; (2008); p. 156 - 162, View in Reaxys 7 of 11
Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- chloroform-d1 scopy) Original Text (NMR Spectroscopy)
IHNMR S : 4.53 (s, 2H), 5.98 (s, 2H), 6.75-6. 88 (m, 3H).
Comment (NMR Spectroscopy)
Signals given
Patent; HAN, Sang Min; LEE, Myung Hee; CHOI, Won Chul; WO2005/70915; (2005); (A1) English, View in Reaxys 8 of 11
Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
200
Original Text (NMR Spectroscopy)
1H
Comment (NMR Spectroscopy)
Signals given
NMR (200MHz, CDCl3) : No. 6.88-6.75 (m, 3H), 5.97 (s, 2H), 4.53 (s, 2H)
Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; JEIL PHARM. CO., LTD.; KOREA RESEARCH INSTITUTE OF BIOSCIENCE AND BIOTECHNOLOGY; CJ CORP.; WO2005/100303; (2005); (A1) English, View in Reaxys 9 of 11
Nucleus (NMR Spectroscopy)
1H
Coupling Nuclei
1H
Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]
200
Bourry, Anne; Akue-Gedu, Rufine; Rigo, Benoit; Henichart, Jean-Pierre; Sanz, Gerard; Couturier, Daniel; Journal of Heterocyclic Chemistry; vol. 40; nb. 6; (2003); p. 989 - 993, View in Reaxys 10 of 11
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]
200
Bourry, Anne; Akue-Gedu, Rufine; Rigo, Benoit; Henichart, Jean-Pierre; Sanz, Gerard; Couturier, Daniel; Journal of Heterocyclic Chemistry; vol. 40; nb. 6; (2003); p. 989 - 993, View in Reaxys 11 of 11
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
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Solvents (NMR Spectro- CDCl3 scopy) Pelter, Andrew; Ward, Robert S.; Pritchard, Martyn C.; Kay, I. Trevor; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1988); p. 1615 - 1624, View in Reaxys Mass Spectrometry (2) Description (Mass References Spectrometry) liquid chromatog- Porcal, Williams; Merlino, Alicia; Boiani, Mariana; Gerpe, Alejandra; Gonzalez, Mercedes; Cerecetto, raphy mass spec- Hugo; Organic Process Research and Development; vol. 12; nb. 2; (2008); p. 156 - 162, View in Reaxys trometry (LCMS); electrospray ionisation (ESI); spectrum spectrum; electron impact (EI); chemical ionization (CI)
Staack, Roland F.; Maurer, Hans H.; Journal of Mass Spectrometry; vol. 39; nb. 3; (2004); p. 255 - 261, View in Reaxys
Reaxys ID 4927407 View in Reaxys
2/2 CAS Registry Number: 73956-81-7 Chemical Name: hexamethylenetetramine; compound with 5chloromethyl-benzo[1,3]dioxole; Hexamethylentetramin; Verbindung mit 5-Chlormethyl-benzo[1,3]dioxol Linear Structure Formula: C8H7ClO2*C6H12N4 Molecular Formula: C6H12N4*C8H7ClO2 Molecular Weight: 310.783 Type of Substance: heterocyclic InChI Key: FCBPBQFDYTVZAR-UHFFFAOYSA-N Note:
N N
N N
Cl
O O
Druglikeness (1) 1 of 1
LogP
1.788
H Bond Donors
0
H Bond Acceptors
4
Rotatable Bonds
1
TPSA
31.42
Lipinski Number
4
Veber Number
2
Melting Point (1) 1 of 1
Melting Point [°C]
203 - 204
Comment (Melting Point)
Decomposition.
Jacobs; Heidelberger; Journal of Biological Chemistry; vol. 20; (1915); p. 674, View in Reaxys
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