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Quinolizidines. VII. Structure of O-Methylpsychotrine : The Endocyclic versus the Exocyclic Double Bond Structure in the Dihydroisoquinoline Moiety
http://hdl.handle.net/2297/7615
http://hdl.handle.net/2297/7615a72950b5-b8e9-4b98-9476-f5dd24caeaa7
| 名前 / ファイル | ライセンス | アクション |
|---|---|---|
PH-PR-OHBA-M-598.pdf (1.3 MB)
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| Item type | 学術雑誌論文 / Journal Article(1) | |||||
|---|---|---|---|---|---|---|
| 公開日 | 2017-10-03 | |||||
| タイトル | ||||||
| タイトル | Quinolizidines. VII. Structure of O-Methylpsychotrine : The Endocyclic versus the Exocyclic Double Bond Structure in the Dihydroisoquinoline Moiety | |||||
| 言語 | ||||||
| 言語 | eng | |||||
| 資源タイプ | ||||||
| 資源タイプ識別子 | http://purl.org/coar/resource_type/c_6501 | |||||
| 資源タイプ | journal article | |||||
| 著者 |
Fujii, Tozo
× Fujii, Tozo× Ohba, Masashi× Yonemitsu, Osamu× Ban, Yoshio |
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| 書誌情報 |
Chemical & pharmaceutical bulletin 巻 30, 号 2, p. 598-609, 発行日 1982-02-25 |
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| ISSN | ||||||
| 収録物識別子タイプ | ISSN | |||||
| 収録物識別子 | 0009-2363 | |||||
| NCID | ||||||
| 収録物識別子タイプ | NCID | |||||
| 収録物識別子 | AA00602100 | |||||
| DOI | ||||||
| 関連タイプ | isIdenticalTo | |||||
| 識別子タイプ | DOI | |||||
| 関連識別子 | 10.1248/cpb.30.598 | |||||
| 出版者 | ||||||
| 出版者 | 日本薬学会 | |||||
| 抄録 | ||||||
| 内容記述タイプ | Abstract | |||||
| 内容記述 | By comparison of its ultraviolet spectra in H_2O at various pH's with those of model compounds, 11,14,16,17,and 18,the Ipecac alkaloid O-methylpsychotrine has been shown to have the genuine 3,4-dihydroisoquinoline structure (1), not the exocyclic double bond structure (4), in the free base form as well as in the protonated form. The ^1H nuclear magnetic resonance (NMR) and ^<13>C NMR spectra of the alkaloid have also confirmed this endocyclic double bond structure in the dihydroisoquinoline moiety. These results indicate that the position of the double bond for simple 1-alkyl-3,4-dihydroisoquinolines is endocyclic, and factors that stabilize the exocyclic double bond structure are discussed. 1-tert-Butyl-3,4-dihydro-6,7-dimethoxy-2-methylisoquinolinium iodide (30) has been found to be unstable in H_2O. On heating in H_2O at 90℃ for 10 min, it underwent ring opening to give 27 in good yield. The acid dissociation constants for 1-methyl-(16) and 1-tert-butyl-3,4-dihydro-6,7-dimethoxyisoquinoline (18) in H_2O at 20℃ were spectrometrically determined to be 9.16±0.02 and 8.80±0.02,respectively. | |||||
| 著者版フラグ | ||||||
| 出版タイプ | VoR | |||||
| 出版タイプResource | http://purl.org/coar/version/c_970fb48d4fbd8a85 | |||||
