Query Query
Results
Date
3 substances in Reaxys
2016-09-16 17h:16m:37s (EST)
N OH
1. Query
Search as: As drawn, No salts, No mixtures, No isotopes, No charges, No radicals
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Reaxys ID 508872 View in Reaxys
1/3
N
CAS Registry Number: 13213-36-0 Chemical Name: 1-phenylpropan-2-one oxime; phenylacetone oxime Linear Structure Formula: C9H11ON Molecular Formula: C9H11NO Molecular Weight: 149.192 Type of Substance: isocyclic InChI Key: AUYFJUMCPAMOKN-UHFFFAOYSA-N Note:
OH
Substance Label (34) Label References 5
Wessling, Michael; Schäfer, Hans J.; Beilstein Journal of Organic Chemistry; vol. 11; (2015); p. 1163 1174, View in Reaxys
1i
Xuan, Jun; Xia, Xu-Dong; Zeng, Ting-Ting; Feng, Zhu-Jia; Chen, Jia-Rong; Lu, Liang-Qiu; Xiao, WenJing; Angewandte Chemie - International Edition; vol. 53; nb. 22; (2014); p. 5653 - 5656; Angew. Chem.; vol. 126; nb. 22; (2014); p. 5759 - 5762,4, View in Reaxys
T1, E5, Ketoxime
Sardarian; Shahsavari-Fard; Shahsavari; Ebrahimi; Tetrahedron Letters; vol. 48; nb. 14; (2007); p. 2639 2643, View in Reaxys
5b
Bures, Jordi; Isart, Carles; Vilarrasa, Jaume; Organic Letters; vol. 9; nb. 22; (2007); p. 4635 - 4638, View in Reaxys
T.4, Entry 16,Sub- Shirini; Esm-Hosseini; Hejazi; Mohammadpoor-Baltork; Journal of Chemical Research; nb. 1; (2006); p. strate 29 - 31, View in Reaxys 13
Wipf, Peter; Fletcher, Joan M.; Scarone, Laura; Tetrahedron Letters; vol. 46; nb. 33; (2005); p. 5463 5466, View in Reaxys
Table I, entry 7
Kiasat, Ali Reza; Kazemi, Foad; Nourbakhsh, Kazem; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 179; nb. 6; (2004); p. 1193 - 1196, View in Reaxys
Tab. 1., Ent. 3., educt
Dongare, Mohan K.; Bhagwat, Vivekanand V.; Ramana; Gurjar, Mukund K.; Tetrahedron Letters; vol. 45; nb. 24; (2004); p. 4759 - 4762, View in Reaxys
3b
Torii, Sigeru; Tanaka, Hideo; Katoh, Tetsuo; Chemistry Letters; (1983); p. 607 - 610, View in Reaxys; Hwu, Jih Ru; Tseng, Wen Nan; Patel, Himatkumar V.; Wong, Fong Fuh; Horng, Den-Nan; Liaw, Ben Ruey; Lung Ching, Lin; Journal of Organic Chemistry; vol. 64; nb. 7; (1999); p. 2211 - 2218, View in Reaxys
4, R=C6H5
Kim, Kil Joong; Kim, Kyongtae; Heterocycles; vol. 50; nb. 1; (1999); p. 147 - 157, View in Reaxys
2; AMPH oxime
Cashman, John R.; Xiong, Yeng N.; Lifen, Xu; Janowsky, Aaron; Journal of Pharmacology and Experimental Therapeutics; vol. 288; nb. 3; (1999); p. 1251 - 1260, View in Reaxys
2e
Tomioka, Hideo; Ueda, Koichi; Ohi, Hirofumi; Izawa, Yasuji; Chemistry Letters; (1986); p. 1359 - 1362, View in Reaxys; Iesce, M. Rosaria; Cermola, Flavio; Guitto, Antonio; Synthesis; nb. 6; (1997); p. 657 660, View in Reaxys
PhCH2(CH3)C=N Marques, C. A.; Selva, M.; Tundo, P.; Montanari, F.; Journal of Organic Chemistry; vol. 58; nb. 21; (1993); OH p. 5765 - 5770, View in Reaxys 53a
Hall, J. Herbert; Chien, Joseph Yuming; Kauffman, Joel M.; Litak, Peter T.; Adams, Jeffrey K.; et al.; Journal of Heterocyclic Chemistry; vol. 29; nb. 5; (1992); p. 1245 - 1273, View in Reaxys
entry 2
Ranu; Chakraborty; Tetrahedron; vol. 48; nb. 25; (1992); p. 5317 - 5322, View in Reaxys
12
Felix, C.; Laurent, A.; Lesniak, S.; Mison, P.; Journal of Chemical Research, Miniprint; nb. 2; (1991); p. 301 - 323, View in Reaxys
entry 4
Ranu, Brindaban C.; Chakraborty, Rupak; Tetrahedron Letters; vol. 32; nb. 29; (1991); p. 3579 - 3582, View in Reaxys
4c
Wessling, Michael; Schaefer, Hans J.; Chemische Berichte; vol. 124; nb. 10; (1991); p. 2303 - 2306, View in Reaxys
Table entry 6 column 1
Barton, H. R. Derek; Bowles, Timothy; Husinec, Suren; Forbes, Judith E.; Llobera, Antonia; et al.; Tetrahedron Letters; vol. 29; nb. 27; (1988); p. 3343 - 3346, View in Reaxys
educt for 6e
Jennings, W. Brian; Watson, Stephen P.; Boyd, Derek R.; Journal of the Chemical Society, Chemical Communications; (1988); p. 931 - 932, View in Reaxys
Table 1, entry 26,col.1
Firouzabadi, H.; Iranpoor, N.; Kiaeezadeh, F.; Toofan, J.; Tetrahedron; vol. 42; nb. 2; (1986); p. 719 - 726, View in Reaxys
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1, table, entry 9
Monti, D.; Gramatica, P.; Speranza, G.; Tagliapietra, S.; Manitto, P.; Synthetic Communications; vol. 16; nb. 7; (1986); p. 803 - 808, View in Reaxys
19
Lozynski, Marek; Rusinska-Roszak, Danuta; Polish Journal of Chemistry; vol. 60; nb. 4-6; (1986); p. 625 630, View in Reaxys
2a
Beckett,A.H. et al.; Tetrahedron; vol. 32; (1976); p. 1267 - 1276, View in Reaxys; Varma, Rajender S.; Varma, Manju; Kabalka, George W.; Tetrahedron Letters; vol. 26; nb. 49; (1985); p. 6013 - 6014, View in Reaxys
5a
Shono, Tatsuya; Hamaguchi, Hiroshi; Mikami, Hiroshi; Nogusa, Hideo; Kashimura, Shigenori; Journal of Organic Chemistry; vol. 48; nb. 12; (1983); p. 2103 - 2105, View in Reaxys
2a (syn/anti)
Beckett,A.H. et al.; Tetrahedron; vol. 32; (1976); p. 1267 - 1276, View in Reaxys
VIa
Beckett; Coutts; Ogunbona; Journal of Pharmacy and Pharmacology; vol. 26; nb. 5; (1974); p. 312 - 316, View in Reaxys
10
Beckett; Coutts; Ogunbona; Tetrahedron; vol. 29; nb. 24; (1973); p. 4189 - 4193, View in Reaxys; Humbert; Laurent; Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques; vol. 272; (1971); p. 1165, View in Reaxys
IIa
Coutts; Malicky; Organic Mass Spectrometry; vol. 7; (1973); p. 985,986, View in Reaxys
(E)-Oxim 1a
Busser,U.; Haller,R.; Tetrahedron Letters; (1973); p. 231 - 232, View in Reaxys
14
Warren,R.G. et al.; Journal of the Chemical Society [Section] D: Chemical Communications; (1971); p. 1521 - 1522, View in Reaxys
VII
Fox et al.; Journal of Organic Chemistry; vol. 35; (1970); p. 4234, View in Reaxys
1
Benington,F. et al.; Journal of Medicinal Chemistry; vol. 8; (1965); p. 100 - 104, View in Reaxys
Va
Dornow,A.; Mueller,A.; Chemische Berichte; vol. 93; (1960); p. 32 - 40, View in Reaxys
Related Structure (1) References Alvernhe; Laurent; Bulletin de la Societe Chimique de France; (1970); p. 3003,3004,3007, View in Reaxys Derivative (1) Derivative 1-phenyl-acetone
References Varma, Rajender S.; Varma, Manju; Kabalka, George W.; Synthetic Communications; vol. 16; nb. 1; (1986); p. 91 - 96, View in Reaxys
Melting Point (8) 1 of 8
Melting Point [°C]
69 - 71
Kiasat, Ali Reza; Javaherian, Mohammad; Daei, Mina; Farbod, Mansoor; Revue Roumaine de Chimie; vol. 60; nb. 9; (2015); p. 875 - 880, View in Reaxys 2 of 8
Melting Point [°C]
87 - 88
Solvent (Melting Point)
hexane
Yamamoto, Yutaro; Hasegawa, Hiroto; Yamataka, Hiroshi; Journal of Organic Chemistry; vol. 76; nb. 11; (2011); p. 4652 - 4660, View in Reaxys 3 of 8
Melting Point [°C]
56 - 57
Solvent (Melting Point)
hexane
Langhals, Heinz; Range, Guenter; Wistuba, Eckehardt; Ruechardt, Christoph; Chemische Berichte; vol. 114; nb. 12; (1981); p. 3813 - 3830, View in Reaxys 4 of 8
Melting Point [°C]
69
Mezheritskaya, L. V.; Matsovskaya, E. S.; Dorofeenko, G. N.; Journal of Organic Chemistry USSR (English Translation); vol. 16; (1980); p. 174 - 178; Zhurnal Organicheskoi Khimii; vol. 16; nb. 1; (1980); p. 183 - 188, View in Reaxys 5 of 8
Melting Point [°C]
68 - 69
Solvent (Melting Point)
diethyl ether
Dornow,A.; Mueller,A.; Chemische Berichte; vol. 93; (1960); p. 32 - 40, View in Reaxys 6 of 8
Melting Point [°C]
68 - 68.5
Jaeger; van Dijk; Pr. Acad. Amsterdam; vol. 44; (1941); p. 26,27, View in Reaxys
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7 of 8
Melting Point [°C]
70
Hey; Journal of the Chemical Society; (1930); p. 18,20, View in Reaxys 8 of 8
Melting Point [°C]
68 - 70
Neber; v. Friedolsheim; Justus Liebigs Annalen der Chemie; vol. 449; (1926); p. 129, View in Reaxys Boiling Point (4) Boiling Point [°C]
Pressure (Boiling Point) [Torr]
References
109
0.4
Langhals, Heinz; Range, Guenter; Wistuba, Eckehardt; Ruechardt, Christoph; Chemische Berichte; vol. 114; nb. 12; (1981); p. 3813 - 3830, View in Reaxys
107
0.7
Alvernhe; Laurent; Bulletin de la Societe Chimique de France; (1970); p. 3003,3004,3007, View in Reaxys
101 - 103
3
Biela,R. et al.; Journal fuer Praktische Chemie (Leipzig); vol. 33; (1966); p. 282 - 292, View in Reaxys
142 - 143
15
Prajsnar; Zeszyty Naukowe Politechniki Slaskiej, Chemia; vol. 20; (1963); p. 1,72, View in Reaxys
Refractive Index (1) Refractive Index Wavelength (Refractive Index) [nm]
Temperature (Refractive Index) [°C]
References
1.5454
20
Prajsnar; Zeszyty Naukowe Politechniki Slaskiej, Chemia; vol. 20; (1963); p. 1,72, View in Reaxys
589
Density (1) 1 of 1
Density [g·cm-3]
1.23
Type (Density)
crystallographic
Jaeger; van Dijk; Pr. Acad. Amsterdam; vol. 44; (1941); p. 26,27, View in Reaxys Conformation (1) Object of Investi- References gation Conformation
Alvernhe; Laurent; Bulletin de la Societe Chimique de France; (1970); p. 3003,3004,3007, View in Reaxys
Crystal Phase (2) Description (Crys- Comment (Crystal References tal Phase) Phase) Crystal structure determination
β=89.5 grad, a=8.65 Angstroem, b=16.58 Angstroem, c=5.46 Angstroem, n=4.; aus dem RoentgenDiagramm ermittelt.
Crystal structure determination
Jaeger; van Dijk; Pr. Acad. Amsterdam; vol. 44; (1941); p. 26,27, View in Reaxys
Crystal Property Description (1) Colour & Other Location Properties colourless
Jaeger; van Dijk; Pr. Acad. Amsterdam; vol. 44; (1941); p. 26,27, View in Reaxys
supporting information
References Moran, Joseph; Pfeiffer, Jennifer Y.; Gorelsky, Serge I.; Beauchemin, Andre M.; Organic Letters; vol. 11; nb. 9; (2009); p. 1895 - 1898, View in Reaxys
Crystal System (1) Crystal System References monoclinic
Jaeger; van Dijk; Pr. Acad. Amsterdam; vol. 44; (1941); p. 26,27, View in Reaxys
Further Information (1) Description (Fur- References ther Information) Further information
Coutts; Malicky; Organic Mass Spectrometry; vol. 7; (1973); p. 985,986, View in Reaxys
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NMR Spectroscopy (15) 1 of 15
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
400
Yamamoto, Yutaro; Hasegawa, Hiroto; Yamataka, Hiroshi; Journal of Organic Chemistry; vol. 76; nb. 11; (2011); p. 4652 - 4660, View in Reaxys 2 of 15
Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]
75
Comment (NMR Spectroscopy)
two stereoisomers
Beauchemin, Andre M.; Moran, Joseph; Lebrun, Marie-Eve; Seguin, Catherine; Dimitrijevic, Elena; Zhang, Lili; Gorelsky, Serge I.; Angewandte Chemie - International Edition; vol. 47; nb. 8; (2008); p. 1410 - 1413, View in Reaxys 3 of 15
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]
75
Beauchemin, Andre M.; Moran, Joseph; Lebrun, Marie-Eve; Seguin, Catherine; Dimitrijevic, Elena; Zhang, Lili; Gorelsky, Serge I.; Angewandte Chemie - International Edition; vol. 47; nb. 8; (2008); p. 1410 - 1413, View in Reaxys 4 of 15
Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]
300
Comment (NMR Spectroscopy)
two stereoisomers
Beauchemin, Andre M.; Moran, Joseph; Lebrun, Marie-Eve; Seguin, Catherine; Dimitrijevic, Elena; Zhang, Lili; Gorelsky, Serge I.; Angewandte Chemie - International Edition; vol. 47; nb. 8; (2008); p. 1410 - 1413, View in Reaxys 5 of 15
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- chloroform-d1 scopy)
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Frequency (NMR Spectroscopy) [MHz]
400
Location
supporting information
Portela-Cubillo, Fernando; Lymer, James; Scanlan, Eoin M.; Scott, Jackie S.; Walton, John C.; Tetrahedron; vol. 64; nb. 52; (2008); p. 11908 - 11916, View in Reaxys 6 of 15
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- CDCl3 scopy) Wessling, Michael; Schaefer, Hans J.; Chemische Berichte; vol. 124; nb. 10; (1991); p. 2303 - 2306, View in Reaxys; Hwu, Jih Ru; Tseng, Wen Nan; Patel, Himatkumar V.; Wong, Fong Fuh; Horng, Den-Nan; Liaw, Ben Ruey; Lung Ching, Lin; Journal of Organic Chemistry; vol. 64; nb. 7; (1999); p. 2211 - 2218, View in Reaxys 7 of 15
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- CDCl3 scopy) Hwu, Jih Ru; Tseng, Wen Nan; Patel, Himatkumar V.; Wong, Fong Fuh; Horng, Den-Nan; Liaw, Ben Ruey; Lung Ching, Lin; Journal of Organic Chemistry; vol. 64; nb. 7; (1999); p. 2211 - 2218, View in Reaxys 8 of 15
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- CCl4 scopy) Ranu; Chakraborty; Tetrahedron; vol. 48; nb. 25; (1992); p. 5317 - 5322, View in Reaxys 9 of 15
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Beckett,A.H. et al.; Tetrahedron; vol. 32; (1976); p. 1267 - 1276, View in Reaxys 10 of 15
Description (NMR Spec- NMR troscopy) Beckett; Coutts; Ogunbona; Journal of Pharmacy and Pharmacology; vol. 26; nb. 5; (1974); p. 312 - 316, View in Reaxys
11 of 15
Description (NMR Spec- NMR troscopy) Comment (NMR Spectroscopy)
syn-anti-Gemisch
Lindeke et al.; Acta Pharmaceutica Suecica; vol. 10; (1973); p. 493,500, View in Reaxys 12 of 15
Description (NMR Spec- NMR troscopy) Comment (NMR Spectroscopy)
1H- ( anti/syn = 7/3 )
Alvernhe; Laurent; Bulletin de la Societe Chimique de France; (1970); p. 3003,3004,3007, View in Reaxys 13 of 15
Description (NMR Spec- NMR troscopy) Comment (NMR Spectroscopy)
1H; Einfluss v. HCl auf chemical shift; Konzentr.-abhaengigkeit
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Fox et al.; Journal of Organic Chemistry; vol. 35; (1970); p. 4234, View in Reaxys 14 of 15
Description (NMR Spec- Spectrum troscopy) Comment (NMR Spectroscopy)
Bzl., CCl4
Lustig; Journal of Physical Chemistry; vol. 65; (1961); p. 491,493,494; Chem.Abstr.; nb. 22183; (1959), View in Reaxys 15 of 15
Description (NMR Spec- NMR troscopy) Comment (NMR Spectroscopy)
Unters. zur syn-anti-Isomerie
Lustig; Journal of Physical Chemistry; vol. 65; (1961); p. 491,493,494; Chem.Abstr.; nb. 22183; (1959), View in Reaxys IR Spectroscopy (4) 1 of 4
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
neat (no solvent)
Comment (IR Spectroscopy)
3250 - 922 1/cm
Hwu, Jih Ru; Tseng, Wen Nan; Patel, Himatkumar V.; Wong, Fong Fuh; Horng, Den-Nan; Liaw, Ben Ruey; Lung Ching, Lin; Journal of Organic Chemistry; vol. 64; nb. 7; (1999); p. 2211 - 2218, View in Reaxys 2 of 4
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
neat (no solvent)
Comment (IR Spectroscopy)
3280 - 1665 cm**(-1)
Ranu; Chakraborty; Tetrahedron; vol. 48; nb. 25; (1992); p. 5317 - 5322, View in Reaxys 3 of 4
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
neat (no solvent)
Comment (IR Spectroscopy)
3500 - 1660 cm**(-1)
Wessling, Michael; Schaefer, Hans J.; Chemische Berichte; vol. 124; nb. 10; (1991); p. 2303 - 2306, View in Reaxys 4 of 4
Description (IR Spectroscopy)
Bands
Warren,R.G. et al.; Journal of the Chemical Society [Section] D: Chemical Communications; (1971); p. 1521 - 1522, View in Reaxys Mass Spectrometry (3) Description (Mass References Spectrometry) spectrum
Hwu, Jih Ru; Tseng, Wen Nan; Patel, Himatkumar V.; Wong, Fong Fuh; Horng, Den-Nan; Liaw, Ben Ruey; Lung Ching, Lin; Journal of Organic Chemistry; vol. 64; nb. 7; (1999); p. 2211 - 2218, View in Reaxys
spectrum; electron impact (EI)
Wessling, Michael; Schaefer, Hans J.; Chemische Berichte; vol. 124; nb. 10; (1991); p. 2303 - 2306, View in Reaxys Coutts; Malicky; Organic Mass Spectrometry; vol. 7; (1973); p. 985,986, View in Reaxys
UV/VIS Spectroscopy (1) 1 of 1
Description (UV/VIS Spectroscopy)
Absorption maxima
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Warren,R.G. et al.; Journal of the Chemical Society [Section] D: Chemical Communications; (1971); p. 1521 - 1522, View in Reaxys Pharmacological Data (13) 1 of 13
Comment (Pharmacological Data)
Bioactivities present
Patent; Stauffer Chemical Company; US4137308; (1979); (A1) English, View in Reaxys; Dornow,A.; Mueller,A.; Chemische Berichte; vol. 93; (1960); p. 32 - 40, View in Reaxys; Dornow,A. et al.; Chemische Berichte; vol. 94; (1961); p. 67 - 76, View in Reaxys; Rapoport,H.; Nilsson,W.; Journal of the American Chemical Society; vol. 83; (1961); p. 4262 - 4267, View in Reaxys; Benington,F. et al.; Journal of Medicinal Chemistry; vol. 8; (1965); p. 100 104, View in Reaxys; Beckett; Coutts; Ogunbona; Tetrahedron; vol. 29; nb. 24; (1973); p. 4189 - 4193, View in Reaxys; Beckett,A.H. et al.; Tetrahedron; vol. 32; (1976); p. 1267 - 1276, View in Reaxys; Diekmann,H.; Luettke,W.; Angewandte Chemie; vol. 80; (1968); p. 395, View in Reaxys; Julliard,M.; Bulletin de la Societe Chimique de France; (1970); p. 2001 - 2004, View in Reaxys; Warren,R.G. et al.; Journal of the Chemical Society [Section] D: Chemical Communications; (1971); p. 1521 - 1522, View in Reaxys; Loev,B.; Kormendy,M.F.; Journal of Organic Chemistry; vol. 28; (1963); p. 3421 - 3426, View in Reaxys; Chu,S.-Y.; Coviello,D.A.; Journal of Organic Chemistry; vol. 36; (1971); p. 3467 - 3469, View in Reaxys; Gribble,G.W. et al.; Synthesis; (1977); p. 856 - 859, View in Reaxys; Busser,U.; Haller,R.; Tetrahedron Letters; (1973); p. 231 - 232, View in Reaxys; Biela,R. et al.; Journal fuer Praktische Chemie (Leipzig); vol. 33; (1966); p. 282 - 292, View in Reaxys; Diekmann,H.; Luettke,W.; Angewandte Chemie; vol. 80; (1968); p. 395 - 396, View in Reaxys; Gilsdorf; Nord; Journal of the American Chemical Society; vol. 74; (1952); p. 1837,1841, View in Reaxys; Kolb; Justus Liebigs Annalen der Chemie; vol. 291; (1896); p. 267, View in Reaxys; Neber; v. Friedolsheim; Justus Liebigs Annalen der Chemie; vol. 449; (1926); p. 129, View in Reaxys; Smith; Journal of the American Chemical Society; vol. 70; (1948); p. 320,322; Journal of the American Chemical Society; vol. 76; (1954); p. 436,441, View in Reaxys 2 of 13
Comment (Pharmacological Data)
Bioactivities present
Hey; Journal of the Chemical Society; (1930); p. 18,20, View in Reaxys; Harlay; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 213; (1941); p. 304, View in Reaxys; Rheinboldt; Dewald; Justus Liebigs Annalen der Chemie; vol. 455; (1927); p. 307, View in Reaxys; Hass et al.; Journal of Organic Chemistry; vol. 15; (1950); p. 8,13, View in Reaxys; Dollfus; Chemische Berichte; vol. 25; (1892); p. 1918; Chemische Berichte; vol. 26; (1893); p. 1971, View in Reaxys; Patent; Purdue Research Found.; US2233823; (1939), View in Reaxys; Jaeger; van Dijk; Pr. Acad. Amsterdam; vol. 44; (1941); p. 26,27, View in Reaxys; Jaeger; van Dijk; Proceedings of the Koninklijke Nederlandse Akademie van Wetenschappen, Series B: Physical Sciences; vol. 44; (1941); p. 26,36,37, View in Reaxys; Patent; Purdue Research Found; US2233823; (1939), View in Reaxys; Larsson; Chalmers Handl.; nb. 94; (1950); p. 21,26, View in Reaxys; Kitahonoki et al.; Tetrahedron Letters; (1965); p. 1059,1061, View in Reaxys; Humbert; Laurent; Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques; vol. 272; (1971); p. 1165, View in Reaxys; Alvernhe; Laurent; Bulletin de la Societe Chimique de France; (1970); p. 3003,3004,3007, View in Reaxys; Lustig; Journal of Physical Chemistry; vol. 65; (1961); p. 491,493,494; Chem.Abstr.; nb. 22183; (1959), View in Reaxys; Coutts; Malicky; Organic Mass Spectrometry; vol. 7; (1973); p. 985,986, View in Reaxys; Fox et al.; Journal of Organic Chemistry; vol. 35; (1970); p. 4234, View in Reaxys; Prajsnar; Zeszyty Naukowe Politechniki Slaskiej, Chemia; vol. 20; (1963); p. 1,72, View in Reaxys; Lindeke et al.; Acta Pharmaceutica Suecica; vol. 10; (1973); p. 493,500, View in Reaxys; Beckett; Coutts; Ogunbona; Journal of Pharmacy and Pharmacology; vol. 26; nb. 5; (1974); p. 312 - 316, View in Reaxys; Kabalka, George W.; Pace, R. David; Wadgaonkar, P.P.; Synthetic Communications; vol. 20; nb. 16; (1990); p. 2453 - 2458, View in Reaxys 3 of 13
Comment (Pharmacological Data)
Bioactivities present
Varma, Rajender S.; Varma, Manju; Kabalka, George W.; Tetrahedron Letters; vol. 26; nb. 49; (1985); p. 6013 6014, View in Reaxys; Krzyzanowska, B.; Stec, W. J.; Synthesis; nb. 4; (1982); p. 270 - 273, View in Reaxys; Shono, Tatsuya; Hamaguchi, Hiroshi; Mikami, Hiroshi; Nogusa, Hideo; Kashimura, Shigenori; Journal of Organic Chemistry; vol. 48; nb. 12; (1983); p. 2103 - 2105, View in Reaxys; Felix, C.; Laurent, A.; Lesniak, S.; Mison, P.; Journal of Chemical Research, Miniprint; nb. 2; (1991); p. 301 - 323, View in Reaxys; Ranu, Brindaban C.; Chakraborty, Rupak; Tetrahedron Letters; vol. 32; nb. 29; (1991); p. 3579 - 3582, View in Reaxys; Wessling, Michael; Schaefer, Hans J.; Chemische Berichte; vol. 124; nb. 10; (1991); p. 2303 - 2306, View in Reaxys; Firouzabadi, H.; Iranpoor, N.; Kiaeezadeh, F.; Toofan, J.; Tetrahedron; vol. 42; nb. 2; (1986); p. 719 - 726, View in Reaxys; Barton, H. R. Derek; Bowles, Timothy; Husinec, Suren; Forbes, Judith E.; Llobera, Antonia; et al.; Tetrahedron Letters; vol. 29; nb. 27; (1988); p. 3343 - 3346, View in Reaxys; Langhals, Heinz; Range, Guenter; Wistuba, Eckehardt; Ruechardt, Christoph; Chemische Berichte; vol. 114; nb. 12; (1981); p. 3813 - 3830, View in Reaxys; Landor, Stephen R.; Chan, Yuet M.; Sonola, Olutunji O.; Tatchell, Austin R.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 3; (1984); p. 493 - 496, View in Reaxys; Mezheritskaya, L. V.; Matsovskaya, E. S.; Dorofeenko, G. N.; Journal of Organic Chemistry USSR (English Translation); vol. 16; (1980); p. 174 - 178; Zhurnal Organicheskoi Khimii; vol. 16; nb. 1; (1980); p. 183 - 188, View in Reaxys; Ranu; Chakraborty; Tetrahedron; vol. 48; nb. 25; (1992); p. 5317 - 5322, View in Reaxys; Tomioka, Hideo; Ueda, Koichi; Ohi, Hirofumi; Izawa, Yasuji; Chemistry Letters; (1986); p. 1359 - 1362, View in Reaxys; Torii, Sigeru; Tanaka, Hideo; Katoh, Tetsuo; Chemistry Letters; (1983); p. 607 - 610, View in Reaxys; Miyashita; Matsumura; Kasahara; Shimadzu; Hashimoto; Chemical and Pharmaceutical Bulletin; vol. 30; nb. 3; (1982); p. 887 - 898, View in Reaxys; Hall, J. Herbert; Chien, Joseph Yuming; Kauffman, Joel M.; Litak, Peter T.; Adams, Jeffrey K.;
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et al.; Journal of Heterocyclic Chemistry; vol. 29; nb. 5; (1992); p. 1245 - 1273, View in Reaxys; Monti, D.; Gramatica, P.; Speranza, G.; Tagliapietra, S.; Manitto, P.; Synthetic Communications; vol. 16; nb. 7; (1986); p. 803 - 808, View in Reaxys; Varma, Rajender S.; Varma, Manju; Kabalka, George W.; Synthetic Communications; vol. 16; nb. 1; (1986); p. 91 - 96, View in Reaxys; Marques, C. A.; Selva, M.; Tundo, P.; Montanari, F.; Journal of Organic Chemistry; vol. 58; nb. 21; (1993); p. 5765 - 5770, View in Reaxys; Lozynski, Marek; Rusinska-Roszak, Danuta; Polish Journal of Chemistry; vol. 60; nb. 4-6; (1986); p. 625 - 630, View in Reaxys 4 of 13
Comment (Pharmacological Data)
Bioactivities present
Hanquet, Gilles; Lusinchi, Xavier; Tetrahedron; vol. 50; nb. 42; (1994); p. 12185 - 12200, View in Reaxys; Jennings, W. Brian; Watson, Stephen P.; Boyd, Derek R.; Journal of the Chemical Society, Chemical Communications; (1988); p. 931 - 932, View in Reaxys; Riddell, Frank G.; Rogerson, Martin; Journal of the Chemical Society. Perkin Transactions 2; nb. 2; (1997); p. 249 - 255, View in Reaxys; Iesce, M. Rosaria; Cermola, Flavio; Guitto, Antonio; Synthesis; nb. 6; (1997); p. 657 - 660, View in Reaxys; Hwu, Jih Ru; Tseng, Wen Nan; Patel, Himatkumar V.; Wong, Fong Fuh; Horng, Den-Nan; Liaw, Ben Ruey; Lung Ching, Lin; Journal of Organic Chemistry; vol. 64; nb. 7; (1999); p. 2211 - 2218, View in Reaxys; Kim, Kil Joong; Kim, Kyongtae; Heterocycles; vol. 50; nb. 1; (1999); p. 147 - 157, View in Reaxys; Katritzky, Alan R.; Cui, Xilin; Long, Qiuhe; Yang, Baozhen; Wilcox, Allan L.; Zhang, Yong-Kang; Organic Preparations and Procedures International; vol. 32; nb. 2; (2000); p. 175 - 183, View in Reaxys; Dongare, Mohan K.; Bhagwat, Vivekanand V.; Ramana; Gurjar, Mukund K.; Tetrahedron Letters; vol. 45; nb. 24; (2004); p. 4759 - 4762, View in Reaxys; Kiasat, Ali Reza; Kazemi, Foad; Nourbakhsh, Kazem; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 179; nb. 6; (2004); p. 1193 - 1196, View in Reaxys; Wipf, Peter; Fletcher, Joan M.; Scarone, Laura; Tetrahedron Letters; vol. 46; nb. 33; (2005); p. 5463 - 5466, View in Reaxys; Cashman, John R.; Xiong, Yeng N.; Lifen, Xu; Janowsky, Aaron; Journal of Pharmacology and Experimental Therapeutics; vol. 288; nb. 3; (1999); p. 1251 - 1260, View in Reaxys; Shirini; EsmHosseini; Hejazi; Mohammadpoor-Baltork; Journal of Chemical Research; nb. 1; (2006); p. 29 - 31, View in Reaxys; Sardarian; Shahsavari-Fard; Shahsavari; Ebrahimi; Tetrahedron Letters; vol. 48; nb. 14; (2007); p. 2639 - 2643, View in Reaxys; Bures, Jordi; Isart, Carles; Vilarrasa, Jaume; Organic Letters; vol. 9; nb. 22; (2007); p. 4635 - 4638, View in Reaxys; Beauchemin, Andre M.; Moran, Joseph; Lebrun, Marie-Eve; Seguin, Catherine; Dimitrijevic, Elena; Zhang, Lili; Gorelsky, Serge I.; Angewandte Chemie - International Edition; vol. 47; nb. 8; (2008); p. 1410 - 1413, View in Reaxys; Portela-Cubillo, Fernando; Lymer, James; Scanlan, Eoin M.; Scott, Jackie S.; Walton, John C.; Tetrahedron; vol. 64; nb. 52; (2008); p. 11908 - 11916, View in Reaxys; Moran, Joseph; Gorelsky, Serge I.; Dimitrijevic, Elena; Lebrun, Marie-Eve; Bedard, Anne-Catherine; Seguin, Catherine; Beauchemin, Andre M.; Journal of the American Chemical Society; vol. 130; nb. 52; (2008); p. 17893 - 17906, View in Reaxys; Moran, Joseph; Pfeiffer, Jennifer Y.; Gorelsky, Serge I.; Beauchemin, Andre M.; Organic Letters; vol. 11; nb. 9; (2009); p. 1895 - 1898, View in Reaxys; Pathak, Uma; Pandey, Lokesh Kumar; Mathur, Sweta; Suryanarayana; Chemical Communications; nb. 36; (2009); p. 5409 - 5411, View in Reaxys; Durchschein, Katharina; Ferreira-Da Silva, Bianca; Wallner, Silvia; MacHeroux, Peter; Kroutil, Wolfgang; Glueck, Silvia Maria; Faber, Kurt; Green Chemistry; vol. 12; nb. 4; (2010); p. 616 - 619, View in Reaxys 5 of 13
Comment (Pharmacological Data)
Bioactivities present
Rad, Mohammad Navid Soltani; Khalafi-Nezhad, Ali; Behrouz, Somayeh; Amini, Zohreh; Behrouz, Marzieh; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 185; nb. 8; (2010); p. 1658 - 1671, View in Reaxys; Yamamoto, Yutaro; Hasegawa, Hiroto; Yamataka, Hiroshi; Journal of Organic Chemistry; vol. 76; nb. 11; (2011); p. 4652 - 4660, View in Reaxys; Toogood, Helen S.; Fryszkowska, Anna; Hulley, Martyn; Sakuma, Michiyo; Mansell, David; Stephens, Gill M.; Gardiner, John M.; Scrutton, Nigel S.; ChemBioChem; vol. 12; nb. 5; (2011); p. 738 - 749, View in Reaxys; Cai, Zhihua; Liu, Guodu; Jiao, Guangjun; Senanayake, Chris H.; Tang, Wenjun; Synthesis (Germany); vol. 45; nb. 24; (2013); p. 3355 - 3360; Art.No: SS-2013-H0581-OP, View in Reaxys; Loiseau, Francis; Beauchemin, Andre M.; Organic Syntheses; vol. 90; (2013); p. 87 - 95, View in Reaxys; Xuan, Jun; Xia, Xu-Dong; Zeng, Ting-Ting; Feng, Zhu-Jia; Chen, Jia-Rong; Lu, Liang-Qiu; Xiao, Wen-Jing; Angewandte Chemie - International Edition; vol. 53; nb. 22; (2014); p. 5653 - 5656; Angew. Chem.; vol. 126; nb. 22; (2014); p. 5759 5762,4, View in Reaxys; Wessling, Michael; Schäfer, Hans J.; Beilstein Journal of Organic Chemistry; vol. 11; (2015); p. 1163 - 1174, View in Reaxys; Kiasat, Ali Reza; Javaherian, Mohammad; Daei, Mina; Farbod, Mansoor; Revue Roumaine de Chimie; vol. 60; nb. 9; (2015); p. 875 - 880, View in Reaxys 6 of 13
Effect (Pharmacological Data)
transport; inhibition of
Species or Test-System (Pharmacological Data)
HEK cells expressing human norepinephrine transporter
Method (Pharmacological Data)
cells were pre-incubated with title comp. for 10 min before addition of <3H>NE; then incubated for 10 min; filtered; radioactivity remaining on the filter was measured by liquid scintillation counting
Further Details (Pharmacological Data)
NE: norepinephrine; <3H>NE was used as radiolabel; non-specific uptake was defined in presence of mazindol; Krebs-HEPES buffer; 25 deg C, water bath
Type (Pharmacological Data)
IC50
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Value of Type (Pharmacological Data)
> 10000 nmol/l
Cashman, John R.; Xiong, Yeng N.; Lifen, Xu; Janowsky, Aaron; Journal of Pharmacology and Experimental Therapeutics; vol. 288; nb. 3; (1999); p. 1251 - 1260, View in Reaxys 7 of 13
Effect (Pharmacological Data)
receptor blocking agent
Species or Test-System (Pharmacological Data)
HEK cell membranes expressing human NET
Method (Pharmacological Data)
radioligand binding assay; membranes were isolated; preincubated with title comp. for 10 min before addition of <125I>RTI-55; incubated for 90 min; filtered; radioactivity remaining on the filter was measured by liquid scintillation counting
Further Details (Pharmacological Data)
non-specific binding was defined in presence of mazindol; Krebs-HEPES buffer, room temp., darkness; NET: norepinephrine transporter
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
> 10000 nmol/l
Cashman, John R.; Xiong, Yeng N.; Lifen, Xu; Janowsky, Aaron; Journal of Pharmacology and Experimental Therapeutics; vol. 288; nb. 3; (1999); p. 1251 - 1260, View in Reaxys 8 of 13
Effect (Pharmacological Data)
transport; inhibition of
Species or Test-System (Pharmacological Data)
C6 glioma cells expressing human serotonin transporter
Method (Pharmacological Data)
cells were pre-incubated with <3H>MPP(1+) for 20 min; room temp.; washed; pre-incubated with release buffer for 10 min before title comp. was added; 37 deg C; radioactivity remaining in the cells was measured by liquid scintillation spectrometry
Further Details (Pharmacological Data)
<3H>MPP(1+): <3H>1-methyl-4-phenylpyridinium was used as radiolabel; non-specific uptake was defined in presence of mazindol; Krebs-HEPES buffer, pH 7.4; release was stimulated with trichloroacetic acid
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
1640 nmol/l
Cashman, John R.; Xiong, Yeng N.; Lifen, Xu; Janowsky, Aaron; Journal of Pharmacology and Experimental Therapeutics; vol. 288; nb. 3; (1999); p. 1251 - 1260, View in Reaxys 9 of 13
Effect (Pharmacological Data)
transport; inhibition of
Species or Test-System (Pharmacological Data)
HEK cells expressing human serotonin transporter
Method (Pharmacological Data)
cells were pre-incubated with title comp. for 10 min before addition of <3H>5-HT; then incubated for 10 min; filtered; radioactivity remaining on the filter was measured by liquid scintillation counting
Further Details (Pharmacological Data)
<3H>5-HT: <3H>5-hydroxytryptamine was used as radiolabel; non-specific uptake was defined in presence of imipramine; Krebs-HEPES buffer; 25 deg C, water bath
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
> 10000 nmol/l
Cashman, John R.; Xiong, Yeng N.; Lifen, Xu; Janowsky, Aaron; Journal of Pharmacology and Experimental Therapeutics; vol. 288; nb. 3; (1999); p. 1251 - 1260, View in Reaxys 10 of 13
Effect (Pharmacological Data)
receptor blocking agent
Species or Test-System (Pharmacological Data)
HEK cell membranes expressing human serotonin transporter
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Method (Pharmacological Data)
radioligand binding assay; membranes were isolated; preincubated with title comp. for 10 min before addition of <125I>RTI-55; incubated for 90 min; filtered; radioactivity remaining on the filter was measured by liquid scintillation counting
Further Details (Pharmacological Data)
non-specific binding was defined in presence of imipramine; Krebs-HEPES buffer, room temp., darkness
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
> 10000 nmol/l
Cashman, John R.; Xiong, Yeng N.; Lifen, Xu; Janowsky, Aaron; Journal of Pharmacology and Experimental Therapeutics; vol. 288; nb. 3; (1999); p. 1251 - 1260, View in Reaxys 11 of 13
Effect (Pharmacological Data)
transport; inhibition f
Species or Test-System (Pharmacological Data)
C6 glioma cells expressing human dopamine transporter
Method (Pharmacological Data)
cells were pre-incubated with <3H>MPP(1+) for 20 min; room temp.; washed; pre-incubated with release buffer for 10 min before title comp. was added; 37 deg C; radioactivity remaining in the cells was measured by liquid scintillation spectrometry
Further Details (Pharmacological Data)
<3H>MPP(1+): <3H>1-methyl-4-phenylpyridinium was used as radiolabel; non-specific uptake was defined in presence of mazindol; Krebs-HEPES buffer, pH 7.4; release was stimulated with trichloroacetic acid
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
100 nmol/l
Cashman, John R.; Xiong, Yeng N.; Lifen, Xu; Janowsky, Aaron; Journal of Pharmacology and Experimental Therapeutics; vol. 288; nb. 3; (1999); p. 1251 - 1260, View in Reaxys 12 of 13
Effect (Pharmacological Data)
transport; inhibition of
Species or Test-System (Pharmacological Data)
HEK cells expressing human dopamine transporter
Method (Pharmacological Data)
cells were pre-incubated with title comp. for 10 min before addition of <3H>DA; then incubated for 10 min; filtered; radioactivity remaining on the filter was measured by liquid scintillation counting
Further Details (Pharmacological Data)
DA: dopamine; <3H>DA was used as radiolabel; non-specific uptake was defined in presence of mazindol; Krebs-HEPES buffer; 25 deg C, water bath
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
> 10000 nmol/l
Cashman, John R.; Xiong, Yeng N.; Lifen, Xu; Janowsky, Aaron; Journal of Pharmacology and Experimental Therapeutics; vol. 288; nb. 3; (1999); p. 1251 - 1260, View in Reaxys 13 of 13
Effect (Pharmacological Data)
receptor blocking agent
Species or Test-System (Pharmacological Data)
HEK cell membranes expressing human dopamine transporter
Method (Pharmacological Data)
radioligand binding assay; membranes were isolated; preincubated with title comp. for 10 min before addition of <125I>RTI-55; incubated for 90 min; filtered; radioactivity remaining on the filter was measured by liquid scintillation counting
Further Details (Pharmacological Data)
non-specific binding was defined in presence of mazindol; Krebs-HEPES buffer, room temp., darkness
Type (Pharmacological Data)
Ki
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Value of Type (Pharmacological Data)
> 10000 nmol/l
Cashman, John R.; Xiong, Yeng N.; Lifen, Xu; Janowsky, Aaron; Journal of Pharmacology and Experimental Therapeutics; vol. 288; nb. 3; (1999); p. 1251 - 1260, View in Reaxys
Reaxys ID 2207040 View in Reaxys
EN
2/3 CAS Registry Number: 10048-64-3 Chemical Name: (E)-1-phenylpropan-2-one oxime; trans-phenylpropanone oxime; syn-methyl benzyl ketoxime; E-phenylacetone oxime; Phenylacetone oxime; phenyl-acetone-(E)-oxime; Phenyl-aceton-(E)-oxim Linear Structure Formula: C9H11NO Molecular Formula: C9H11NO Molecular Weight: 149.192 Type of Substance: isocyclic InChI Key: AUYFJUMCPAMOKN-CSKARUKUSA-N Note:
OH
Substance Label (14) Label References 6
Eshghi, Hossein; Hassankhani, Asadollah; Organic Preparations and Procedures International; vol. 37; nb. 6; (2005); p. 575 - 579, View in Reaxys
(E)-2a
Yadav; Subba Reddy; Srinivas; Ramalingam; Synlett; nb. 10; (2000); p. 1447 - 1449, View in Reaxys
2b
Coutts; Jones; Liu; Biomedical Mass Spectrometry; vol. 5; nb. 6; (1978); p. 418 - 422, View in Reaxys; Cashman, John R.; Xiong, Yeng N.; Lifen, Xu; Janowsky, Aaron; Journal of Pharmacology and Experimental Therapeutics; vol. 288; nb. 3; (1999); p. 1251 - 1260, View in Reaxys
10
Lantos; Zhang; Shui; Eggleston; Journal of Organic Chemistry; vol. 58; nb. 25; (1993); p. 7092 - 7095, View in Reaxys
VII-(E)
Krivdin, L. B.; Shcherbakov, V. V.; Kalabin, G. A.; Journal of Organic Chemistry USSR (English Translation); (1986); p. 300 - 305; Zhurnal Organicheskoi Khimii; vol. 22; nb. 2; (1986); p. 342 - 348, View in Reaxys
2b (E isomer)
Varma, Rajender S.; Varma, Manju; Gai, Yuan-Zhu; Kabalka, George W.; Heterocycles; vol. 24; nb. 9; (1986); p. 2581 - 2586, View in Reaxys
2b-E
Varma, Rajender S.; Varma, Manju; Kabalka, George W.; Synthetic Communications; vol. 15; nb. 14; (1985); p. 1325 - 1332, View in Reaxys
9E
Krivdin, Leonid B.; Kalabin, Gennady A.; Nesterenko, Raisa N.; Trofimov, Boris A.; Tetrahedron Letters; vol. 25; nb. 42; (1984); p. 4817 - 4820, View in Reaxys
I
Huitric et al.; Journal of Organic Chemistry; vol. 32; (1967); p. 1661, View in Reaxys; Trofimov, B. A.; Korostova, S. E.; Sobenina, L. N.; Mikhaleva, A. I.; Bzhezovskii, V. M.; et al.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 18; nb. 2; (1982); p. 148 - 152; Khimiya Geterotsiklicheskikh Soedinenii; vol. 18; nb. 2; (1982); p. 193 - 198, View in Reaxys
1 (R&1%=CH3 , R&2%=Ph)
Reddy, Gaddam Subba; Bhatt, M. Vivekananda; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. <B> 20; nb. 4; (1981); p. 322 - 323, View in Reaxys
8
Kim,S.-G. et al.; Bulletin of the Chemical Society of Japan; vol. 52; (1979); p. 1115 - 1120, View in Reaxys
anti-Isomer Ia
Lindeke et al.; Acta Pharmaceutica Suecica; vol. 12; (1975); p. 183,192, 193, View in Reaxys
17
Hawkes,G.E. et al.; Journal of Organic Chemistry; vol. 39; (1974); p. 1017 - 1028, View in Reaxys
Ia
Kotera,K. et al.; Tetrahedron; vol. 24; (1968); p. 5677 - 5690, View in Reaxys
Patent-Specific Data (1) Location in Patent References Claim
Patent; Bramucci, Michael G.; Nagarajan, Vasantha; Chen, Mario W.; US2003/215929; (2003); (A1) English, View in Reaxys
Related Structure (2) Related Structure References
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The author inves- Krivdin, Leonid B.; Kalabin, Gennady A.; Nesterenko, Raisa N.; Trofimov, Boris A.; Tetrahedron Letters; tigated the config- vol. 25; nb. 42; (1984); p. 4817 - 4820, View in Reaxys uration Diese Verb. hat in Kotera,K. et al.; Tetrahedron; vol. 24; (1968); p. 5677 - 5690, View in Reaxys; Huitric et al.; Journal of Orden frueher (s. E ganic Chemistry; vol. 32; (1967); p. 1661, View in Reaxys II 234; E III 1039) beschrieb. kristallinen Praeparaten vorgelegen; Gemische dieser Verb. mit Phenyl(#Z!)-oxim (C9H11NO) haben dagegen in den frueher (s. H 304; E II 234) beschrieb. Praeparaten vorgelegen. Melting Point (4) 1 of 4
Melting Point [°C]
69.5 - 70.5
Kim,S.-G. et al.; Bulletin of the Chemical Society of Japan; vol. 52; (1979); p. 1115 - 1120, View in Reaxys 2 of 4
Melting Point [°C]
69
Solvent (Melting Point)
hexane
Foreman; Siegel; Mrtek; Journal of pharmaceutical sciences; vol. 58; nb. 2; (1969); p. 189 - 192, View in Reaxys 3 of 4
Melting Point [°C]
62 - 63
Solvent (Melting Point)
petroleum ether
Kotera,K. et al.; Tetrahedron; vol. 24; (1968); p. 5677 - 5690, View in Reaxys 4 of 4
Melting Point [°C]
69 - 71
Solvent (Melting Point)
petroleum ether
Huitric et al.; Journal of Organic Chemistry; vol. 32; (1967); p. 1661, View in Reaxys Boiling Point (1) Boiling Point [°C] 81 - 84
Pressure (Boiling Point) [Torr]
References
0.1
Foreman; Siegel; Mrtek; Journal of pharmaceutical sciences; vol. 58; nb. 2; (1969); p. 189 - 192, View in Reaxys
Electrochemical Characteristics (1) 1 of 1
Description (Electrochemical Characteristics)
polarographic half-wave potential
Comment (Electrochem- (wss.-aethanol. Loesungen vom pH 1 und pH 4). ical Characteristics) Nakaya et al.; Nippon Kagaku Zasshi; vol. 80; (1959); p. 1282; Chem.Abstr.; (1961); p. 5192, View in Reaxys NMR Spectroscopy (19) 1 of 19
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- CDCl3 scopy) Temperature (NMR Spectroscopy) [°C]
25
Frequency (NMR Spectroscopy) [MHz]
100
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Eshghi, Hossein; Hassankhani, Asadollah; Organic Preparations and Procedures International; vol. 37; nb. 6; (2005); p. 575 - 579, View in Reaxys 2 of 19
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- CD2Cl2 scopy) Hanquet, Gilles; Lusinchi, Xavier; Tetrahedron; vol. 50; nb. 42; (1994); p. 12185 - 12200, View in Reaxys 3 of 19
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- acetone-d6 scopy) Temperature (NMR Spectroscopy) [°C]
25 - 30
Krivdin, L. B.; Shcherbakov, V. V.; Kalabin, G. A.; Journal of Organic Chemistry USSR (English Translation); (1986); p. 300 - 305; Zhurnal Organicheskoi Khimii; vol. 22; nb. 2; (1986); p. 342 - 348, View in Reaxys 4 of 19
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- CDCl3 scopy) Varma, Rajender S.; Varma, Manju; Gai, Yuan-Zhu; Kabalka, George W.; Heterocycles; vol. 24; nb. 9; (1986); p. 2581 - 2586, View in Reaxys; Varma, Rajender S.; Varma, Manju; Kabalka, George W.; Synthetic Communications; vol. 15; nb. 14; (1985); p. 1325 - 1332, View in Reaxys 5 of 19
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- CDCl3 scopy) Varma, Rajender S.; Varma, Manju; Gai, Yuan-Zhu; Kabalka, George W.; Heterocycles; vol. 24; nb. 9; (1986); p. 2581 - 2586, View in Reaxys; Varma, Rajender S.; Varma, Manju; Kabalka, George W.; Synthetic Communications; vol. 15; nb. 14; (1985); p. 1325 - 1332, View in Reaxys 6 of 19
Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- acetone-d6 scopy) Temperature (NMR Spectroscopy) [°C]
25 - 30
Comment (NMR Spectroscopy)
13C-13C.
Krivdin, L. B.; Shcherbakov, V. V.; Kalabin, G. A.; Journal of Organic Chemistry USSR (English Translation); (1986); p. 300 - 305; Zhurnal Organicheskoi Khimii; vol. 22; nb. 2; (1986); p. 342 - 348, View in Reaxys 7 of 19
Description (NMR Spec- NMR with shift reagents troscopy) Krivdin, L. B.; Shcherbakov, V. V.; Kalabin, G. A.; Journal of Organic Chemistry USSR (English Translation); (1986); p. 300 - 305; Zhurnal Organicheskoi Khimii; vol. 22; nb. 2; (1986); p. 342 - 348, View in Reaxys
8 of 19
Description (NMR Spec- Spin-spin coupling constants troscopy)
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Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Comment (NMR Spectroscopy)
13C-13C. Solvent(s): further solvent(s)
Krivdin, Leonid B.; Kalabin, Gennady A.; Nesterenko, Raisa N.; Trofimov, Boris A.; Tetrahedron Letters; vol. 25; nb. 42; (1984); p. 4817 - 4820, View in Reaxys 9 of 19
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- benzene scopy) Trofimov, B. A.; Korostova, S. E.; Sobenina, L. N.; Mikhaleva, A. I.; Bzhezovskii, V. M.; et al.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 18; nb. 2; (1982); p. 148 - 152; Khimiya Geterotsiklicheskikh Soedinenii; vol. 18; nb. 2; (1982); p. 193 - 198, View in Reaxys 10 of 19
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- CHCl3 scopy) Trofimov, B. A.; Korostova, S. E.; Sobenina, L. N.; Mikhaleva, A. I.; Bzhezovskii, V. M.; et al.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 18; nb. 2; (1982); p. 148 - 152; Khimiya Geterotsiklicheskikh Soedinenii; vol. 18; nb. 2; (1982); p. 193 - 198, View in Reaxys 11 of 19
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide scopy) Trofimov, B. A.; Korostova, S. E.; Sobenina, L. N.; Mikhaleva, A. I.; Bzhezovskii, V. M.; et al.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 18; nb. 2; (1982); p. 148 - 152; Khimiya Geterotsiklicheskikh Soedinenii; vol. 18; nb. 2; (1982); p. 193 - 198, View in Reaxys 12 of 19
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- CCl4 scopy) Trofimov, B. A.; Korostova, S. E.; Sobenina, L. N.; Mikhaleva, A. I.; Bzhezovskii, V. M.; et al.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 18; nb. 2; (1982); p. 148 - 152; Khimiya Geterotsiklicheskikh Soedinenii; vol. 18; nb. 2; (1982); p. 193 - 198, View in Reaxys 13 of 19
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- tetradeuteriomethanol scopy) Trofimov, B. A.; Korostova, S. E.; Sobenina, L. N.; Mikhaleva, A. I.; Bzhezovskii, V. M.; et al.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 18; nb. 2; (1982); p. 148 - 152; Khimiya Geterotsiklicheskikh Soedinenii; vol. 18; nb. 2; (1982); p. 193 - 198, View in Reaxys 14 of 19
Description (NMR Spec- Chemical shifts troscopy)
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Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- nitrobenzene scopy) Trofimov, B. A.; Korostova, S. E.; Sobenina, L. N.; Mikhaleva, A. I.; Bzhezovskii, V. M.; et al.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 18; nb. 2; (1982); p. 148 - 152; Khimiya Geterotsiklicheskikh Soedinenii; vol. 18; nb. 2; (1982); p. 193 - 198, View in Reaxys 15 of 19
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- various solvent(s) scopy) Trofimov, B. A.; Korostova, S. E.; Sobenina, L. N.; Mikhaleva, A. I.; Bzhezovskii, V. M.; et al.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 18; nb. 2; (1982); p. 148 - 152; Khimiya Geterotsiklicheskikh Soedinenii; vol. 18; nb. 2; (1982); p. 193 - 198, View in Reaxys 16 of 19
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Kotera,K. et al.; Tetrahedron; vol. 24; (1968); p. 5677 - 5690, View in Reaxys; Kim,S.-G. et al.; Bulletin of the Chemical Society of Japan; vol. 52; (1979); p. 1115 - 1120, View in Reaxys 17 of 19
Description (NMR Spec- NMR troscopy) Huitric et al.; Journal of Organic Chemistry; vol. 32; (1967); p. 1661, View in Reaxys; Lindeke et al.; Acta Pharmaceutica Suecica; vol. 12; (1975); p. 183,192, 193, View in Reaxys; Glover; Raaen; Journal of Organic Chemistry; vol. 31; (1966); p. 1987, View in Reaxys; Karabatsos; Taller; Tetrahedron; vol. 24; (1968); p. 3347,3353, View in Reaxys
18 of 19
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Hawkes,G.E. et al.; Journal of Organic Chemistry; vol. 39; (1974); p. 1017 - 1028, View in Reaxys 19 of 19
Description (NMR Spec- NMR troscopy) Comment (NMR Spectroscopy)
1H
Foreman; Siegel; Mrtek; Journal of pharmaceutical sciences; vol. 58; nb. 2; (1969); p. 189 - 192, View in Reaxys IR Spectroscopy (3) 1 of 3
Description (IR Spectroscopy)
IR
Lindeke et al.; Acta Pharmaceutica Suecica; vol. 12; (1975); p. 183,192, 193, View in Reaxys 2 of 3
Description (IR Spectroscopy)
Bands
Kotera,K. et al.; Tetrahedron; vol. 24; (1968); p. 5677 - 5690, View in Reaxys 3 of 3
Description (IR Spectroscopy)
Spectrum
Solvent (IR Spectroscopy)
nujol
Comment (IR Spectroscopy)
5000 - 667 cm**(-1)
Gilsdorf; Nord; Journal of the American Chemical Society; vol. 74; (1952); p. 1837,1841, View in Reaxys Mass Spectrometry (2)
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Description (Mass References Spectrometry) spectrum
Coutts; Jones; Liu; Biomedical Mass Spectrometry; vol. 5; nb. 6; (1978); p. 418 - 422, View in Reaxys Lindeke et al.; Acta Pharmaceutica Suecica; vol. 12; (1975); p. 183,192, 193, View in Reaxys
Reaxys ID 2043527 View in Reaxys
3/3 CAS Registry Number: 10048-65-4 Chemical Name: oxime de la 1-phenyl-2-propanone (cis); (Z)-1-phenylpropan-2-one oxime; anti-methyl benzyl ketoxime; cis-phenylpropanone oxime; Z-phenylacetone oxime; benzylmethylketoxime; anti-1-Phenyl-propanon-(2)-oxim Linear Structure Formula: C9H11NO Molecular Formula: C9H11NO Molecular Weight: 149.192 Type of Substance: isocyclic InChI Key: AUYFJUMCPAMOKN-NTMALXAHSA-N Note:
OH ZN
Substance Label (11) Label References (Z)-2a
Yadav; Subba Reddy; Srinivas; Ramalingam; Synlett; nb. 10; (2000); p. 1447 - 1449, View in Reaxys
2a
Cashman, John R.; Xiong, Yeng N.; Lifen, Xu; Janowsky, Aaron; Journal of Pharmacology and Experimental Therapeutics; vol. 288; nb. 3; (1999); p. 1251 - 1260, View in Reaxys
VII-(Z)
Krivdin, L. B.; Shcherbakov, V. V.; Kalabin, G. A.; Journal of Organic Chemistry USSR (English Translation); (1986); p. 300 - 305; Zhurnal Organicheskoi Khimii; vol. 22; nb. 2; (1986); p. 342 - 348, View in Reaxys
2b (Z isomer)
Varma, Rajender S.; Varma, Manju; Gai, Yuan-Zhu; Kabalka, George W.; Heterocycles; vol. 24; nb. 9; (1986); p. 2581 - 2586, View in Reaxys
2c
Hiroi, Kunio; Otsuka, Masahiko; Sato, Shuko; Chemistry Letters; (1985); p. 1907 - 1910, View in Reaxys
2b-Z
Varma, Rajender S.; Varma, Manju; Kabalka, George W.; Synthetic Communications; vol. 15; nb. 14; (1985); p. 1325 - 1332, View in Reaxys
syn-Isomer
Lindeke et al.; Acta Pharmaceutica Suecica; vol. 12; (1975); p. 183,192, 193, View in Reaxys
18
Hawkes,G.E. et al.; Journal of Organic Chemistry; vol. 39; (1974); p. 1017 - 1028, View in Reaxys
anti-Isomer
Alvernhe; Laurent; Bulletin de la Societe Chimique de France; (1970); p. 3003,3004,3007, View in Reaxys
IIa
Kotera,K. et al.; Tetrahedron; vol. 24; (1968); p. 5677 - 5690, View in Reaxys
II
Huitric et al.; Journal of Organic Chemistry; vol. 32; (1967); p. 1661, View in Reaxys
Melting Point (2) 1 of 2
Melting Point [°C]
70
Alvernhe; Laurent; Bulletin de la Societe Chimique de France; (1970); p. 3003,3004,3007, View in Reaxys 2 of 2
Melting Point [°C]
62 - 63
Kotera et al.; Tetrahedron Letters; (1967); p. 841, View in Reaxys Conformation (1) Object of Investi- References gation Conformation
Alvernhe; Laurent; Bulletin de la Societe Chimique de France; (1970); p. 3003,3004,3007, View in Reaxys
NMR Spectroscopy (13) 1 of 13
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- CD2Cl2 scopy)
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Hanquet, Gilles; Lusinchi, Xavier; Tetrahedron; vol. 50; nb. 42; (1994); p. 12185 - 12200, View in Reaxys 2 of 13
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- acetone-d6 scopy) Temperature (NMR Spectroscopy) [°C]
25 - 30
Krivdin, L. B.; Shcherbakov, V. V.; Kalabin, G. A.; Journal of Organic Chemistry USSR (English Translation); (1986); p. 300 - 305; Zhurnal Organicheskoi Khimii; vol. 22; nb. 2; (1986); p. 342 - 348, View in Reaxys 3 of 13
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- CDCl3 scopy) Varma, Rajender S.; Varma, Manju; Gai, Yuan-Zhu; Kabalka, George W.; Heterocycles; vol. 24; nb. 9; (1986); p. 2581 - 2586, View in Reaxys; Varma, Rajender S.; Varma, Manju; Kabalka, George W.; Synthetic Communications; vol. 15; nb. 14; (1985); p. 1325 - 1332, View in Reaxys 4 of 13
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- CDCl3 scopy) Varma, Rajender S.; Varma, Manju; Gai, Yuan-Zhu; Kabalka, George W.; Heterocycles; vol. 24; nb. 9; (1986); p. 2581 - 2586, View in Reaxys; Varma, Rajender S.; Varma, Manju; Kabalka, George W.; Synthetic Communications; vol. 15; nb. 14; (1985); p. 1325 - 1332, View in Reaxys 5 of 13
Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- acetone-d6 scopy) Temperature (NMR Spectroscopy) [°C]
25 - 30
Comment (NMR Spectroscopy)
13C-13C.
Krivdin, L. B.; Shcherbakov, V. V.; Kalabin, G. A.; Journal of Organic Chemistry USSR (English Translation); (1986); p. 300 - 305; Zhurnal Organicheskoi Khimii; vol. 22; nb. 2; (1986); p. 342 - 348, View in Reaxys 6 of 13
Description (NMR Spec- NMR with shift reagents troscopy) Krivdin, L. B.; Shcherbakov, V. V.; Kalabin, G. A.; Journal of Organic Chemistry USSR (English Translation); (1986); p. 300 - 305; Zhurnal Organicheskoi Khimii; vol. 22; nb. 2; (1986); p. 342 - 348, View in Reaxys
7 of 13
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- benzene scopy) Trofimov, B. A.; Korostova, S. E.; Sobenina, L. N.; Mikhaleva, A. I.; Bzhezovskii, V. M.; et al.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 18; nb. 2; (1982); p. 148 - 152; Khimiya Geterotsiklicheskikh Soedinenii; vol. 18; nb. 2; (1982); p. 193 - 198, View in Reaxys
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18/19
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8 of 13
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- CCl4 scopy) Trofimov, B. A.; Korostova, S. E.; Sobenina, L. N.; Mikhaleva, A. I.; Bzhezovskii, V. M.; et al.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 18; nb. 2; (1982); p. 148 - 152; Khimiya Geterotsiklicheskikh Soedinenii; vol. 18; nb. 2; (1982); p. 193 - 198, View in Reaxys 9 of 13
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- nitrobenzene scopy) Trofimov, B. A.; Korostova, S. E.; Sobenina, L. N.; Mikhaleva, A. I.; Bzhezovskii, V. M.; et al.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 18; nb. 2; (1982); p. 148 - 152; Khimiya Geterotsiklicheskikh Soedinenii; vol. 18; nb. 2; (1982); p. 193 - 198, View in Reaxys 10 of 13
Description (NMR Spec- NMR troscopy) Huitric et al.; Journal of Organic Chemistry; vol. 32; (1967); p. 1661, View in Reaxys; Lindeke et al.; Acta Pharmaceutica Suecica; vol. 12; (1975); p. 183,192, 193, View in Reaxys; Karabatsos; Taller; Tetrahedron; vol. 24; (1968); p. 3347,3353, View in Reaxys
11 of 13
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Hawkes,G.E. et al.; Journal of Organic Chemistry; vol. 39; (1974); p. 1017 - 1028, View in Reaxys 12 of 13
Description (NMR Spec- NMR troscopy) Comment (NMR Spectroscopy)
1H-
Alvernhe; Laurent; Bulletin de la Societe Chimique de France; (1970); p. 3003,3004,3007, View in Reaxys 13 of 13
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Kotera,K. et al.; Tetrahedron; vol. 24; (1968); p. 5677 - 5690, View in Reaxys Mass Spectrometry (1) References Lindeke et al.; Acta Pharmaceutica Suecica; vol. 12; (1975); p. 183,192, 193, View in Reaxys
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