Art

J-GLOBAL ID：200902057432472055   Reference number：91A0660599

The Pictet-Spengler Reaction of N_b-Hydroxytryptamines and Cysteinals. II. Temperature Effects, Stereochemistry and Mechanism.

N_b-ヒドロキシトリプタミンとシステイナールとのPictet-Spengler反応 II 温度効果,立体化学および反応機構

Author (4)： LIU J (Shanghai Medical Univ., Shanghai, CHN) ,  NAKAGAWA M (Chiba Univ., Chiba-shi, JPN) ,  OGATA K (Chiba Univ., Chiba-shi, JPN) ,  HINO T (Chiba Univ., Chiba-shi, JPN)
Material： Chemical and Pharmaceutical Bulletin  (Chemical & Pharmaceutical Bulletin)
Volume： 39  Issue： 7  Page： 1672-1676  Publication year： Jul. 1991 
JST Material Number： G0504A  ISSN： 0009-2363  CODEN： CPBTAL  Document type： Article
Article type： 原著論文  Country of issue： Japan (JPN)  Language： ENGLISH (EN)

Thesaurus term： chemical synthesis ,...
Semi thesaurus term： tryptamine ,...

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JST classification (3)： Condensed derivatives of pyrroles  (CF07077C) ,  Aliphatic aldehydes  (CF03180F) ,  Cyclization reaction,ring-opening reaction  (CF02050I)

Substance index (32)： N-Hydroxytryptamine ,  1-Methyl-3-[2-(hydroxyamino)ethyl]-1H-indole ,  (R)-2-[(Methoxycarbonyl)amino]-3-[methylthio]propanal ,  (R)-2-[(tert-Butoxycarbonyl)amino]-3-[methylthio]propanal ,  (R)-2-[(Methoxycarbonyl)amino]-3-[(2,2,2-trichloroethoxycarbonyl)thio]propanal ,  (R)-2-[(tert-Butoxycarbonyl)amino]-3-[(2,2,2-trichloroethoxycarbonyl)thio]propanal ,  (R)-2-[(Benzyloxycarbonyl)amino]-3-[(2,2,2-trichloroethoxycarbonyl)thio]propanal ,  (R)-2-[(2,2,2-Trichloroethoxycarbonyl)amino]-3-[methylthio]propanal ,  (R)-2-[(2,2,2-Trichloroethoxycarbonyl)amino]-3-[(benzyloxycarbonyl)thio]propanal ,  (1S)-1,2,3,4-Tetrahydro-1α-[(R)-1-[(methoxycarbonyl)amino]-2-[methylthio]ethyl]-β-carbolin-2-ol ,  (1S)-1,2,3,4-Tetrahydro-1α-[(R)-1-[(tert-butoxycarbonyl)amino]-2-[methylthio]ethyl]-β-carbolin-2-ol ,  (1S)-1,2,3,4-Tetrahydro-1α-[(R)-1-[(methoxycarbonyl)amino]-2-[(2,2,2-trichloroethoxycarbonyl)thio]ethyl]-β-carbolin-2-ol ,  (1S)-1,2,3,4-Tetrahydro-1α-[(R)-1-[(tert-butoxycarbonyl)amino]-2-[(2,2,2-trichloroethoxycarbonyl)thio]ethyl]-β-carbolin-2-ol ,  (1S)-1,2,3,4-Tetrahydro-1α-[(R)-1-[(benzyloxycarbonyl)amino]-2-[(2,2,2-trichloroethoxycarbonyl)thio]ethyl]-β-carbolin-2-ol ,  (1S)-1,2,3,4-Tetrahydro-1α-[(R)-1-[(2,2,2-trichloroethoxycarbonyl)amino]-2-[methylthio]ethyl]-β-carbolin-2-ol ,  (1S)-1,2,3,4-Tetrahydro-1α-[(R)-1-[(2,2,2-trichloroethoxycarbonyl)amino]-2-[(benzyloxycarbonyl)thio]ethyl]-β-carbolin-2-ol ,  (1R)-1,2,3,4-Tetrahydro-1β-[(R)-1-[(methoxycarbonyl)amino]-2-[methylthio]ethyl]-β-carbolin-2-ol ,  (1R)-1,2,3,4-Tetrahydro-1β-[(R)-1-[(tert-butoxycarbonyl)amino]-2-[methylthio]ethyl]-β-carbolin-2-ol ,  (1R)-1,2,3,4-Tetrahydro-1β-[(R)-1-[(methoxycarbonyl)amino]-2-[(2,2,2-trichloroethoxycarbonyl)thio]ethyl]-β-carbolin-2-ol ,  (1R)-1,2,3,4-Tetrahydro-1β-[(R)-1-[(tert-butoxycarbonyl)amino]-2-[(2,2,2-trichloroethoxycarbonyl)thio]ethyl]-β-carbolin-2-ol ,  (1R)-1,2,3,4-Tetrahydro-1β-[(R)-1-[(benzyloxycarbonyl)amino]-2-[(2,2,2-trichloroethoxycarbonyl)thio]ethyl]-β-carbolin-2-ol ,  (1R)-1,2,3,4-Tetrahydro-1β-[(R)-1-[(2,2,2-trichloroethoxycarbonyl)amino]-2-[methylthio]ethyl]-β-carbolin-2-ol ,  (1R)-1,2,3,4-Tetrahydro-1β-[(R)-1-[(2,2,2-trichloroethoxycarbonyl)amino]-2-[(benzyloxycarbonyl)thio]ethyl]-β-carbolin-2-ol ,  N-[(2R)-3-[Methylthio]-2-[(methoxycarbonyl)amino]propylidene]-2,3-dihydro-1H-indole-3-(ethanamine)N-oxide ,  N-[(2R)-3-[Methylthio]-2-[(tert-butoxycarbonyl)amino]propylidene]-2,3-dihydro-1H-indole-3-(ethanamine)N-oxide ,  N-[(2R)-3-[(2,2,2-Trichloroethoxycarbonyl)thio]-2-[(methoxycarbonyl)amino]propylidene]-2,3-dihydro-1H-indole-3-(ethanamine)N-oxide ,  N-[(2R)-3-[(2,2,2-Trichloroethoxycarbonyl)thio]-2-[(tert-butoxycarbonyl)amino]propylidene]-2,3-dihydro-1H-indole-3-(ethanamine)N-oxide ,  N-[(2R)-3-[(2,2,2-Trichloroethoxycarbonyl)thio]-2-[(benzyloxycarbonyl)amino]propylidene]-2,3-dihydro-1H-indole-3-(ethanamine)N-oxide ,  N-[(2R)-3-[Methylthio]-2-[(2,2,2-trichloroethoxycarbonyl)amino]propylidene]-2,3-dihydro-1H-indole-3-(ethanamine)N-oxide ,  N-[(2R)-3-[(Benzyloxycarbonyl)thio]-2-[(2,2,2-trichloroethoxycarbonyl)amino]propylidene]-2,3-dihydro-1H-indole-3-(ethanamine)N-oxide ,  N-[(2R)-3-[(2,2,2-Trichloroethoxycarbonyl)thio]-2-[(methoxycarbonyl)amino]propylidene]-1-methyl-2,3-dihydro-1H-indole-3-(ethanamine)N-oxide ,  N-[(2R)-3-[Methylthio]-2-[(methoxycarbonyl)amino]propylidene]-1-methyl-2,3-dihydro-1H-indole-3-(ethanamine)N-oxide

Reference (46)：

• 1) a) K.L. Rinehart, Jr., J. Kobayashi, G.C. Harbour, R.G. Hughes, Jr., S.A. Mizsak, and T.A. Scahill, J. Am. Chem. Soc., 106, 1524 (1984)
• b) K.L. Rinehart, Jr., J. Kobayashi, G.C. Harbour, J. Gilmore, M. Mascal, T.G. Holt, L.S. Shield, and F. Lafargue, J. Am. Chem. Soc., 109, 3378 (1987)
• c) J.W. Blunt, R.J. Lake, M.H.G. Munro, and T. Toyokuni, Tetrahedron Lett., 28, 1825 (1987)
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Terms in the title (4)： Nb ,  Pictet-Spengler反応 ,  温度効果 ,  立体化学