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Lactams. XXVI. Regioselectivity in the mercuric acetate- edetic acid oxidation of the ethyl 1-(2-aryl-2-hydroxyethyl)-3- ethyl-4-piperidineacetate system: Enhancement by a benzyloxy group in the aryl moiety and by the 3,4-cis configuration
http://hdl.handle.net/2297/7621
http://hdl.handle.net/2297/7621b72172cd-eb72-4151-ba1f-eccdab6c2e14
| 名前 / ファイル | ライセンス | アクション |
|---|---|---|
PH-PR-OHBA-M-496.pdf (2.4 MB)
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| Item type | 学術雑誌論文 / Journal Article(1) | |||||
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| 公開日 | 2017-10-03 | |||||
| タイトル | ||||||
| タイトル | Lactams. XXVI. Regioselectivity in the mercuric acetate- edetic acid oxidation of the ethyl 1-(2-aryl-2-hydroxyethyl)-3- ethyl-4-piperidineacetate system: Enhancement by a benzyloxy group in the aryl moiety and by the 3,4-cis configuration | |||||
| 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× Tsuchida, Michiko× Saito, Kiyoe× Hirano, Yuko× Sakaguchi, Jun |
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| 書誌情報 |
Chemical & pharmaceutical bulletin 巻 34, 号 2, p. 496-507, 発行日 1986-01-01 |
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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.34.496 | |||||
| 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 | A quantitative analytical study to determine the isomer ratios of the 6-piperidones (type 7) and 2-piperidones (type 5) produced by the mercuric acetate-edetic acid (EDTA) oxidation of 1-(2-aryl-2-hydroxyethyl)-3-alkylpiperidines (±)-4c, d, f, h, 4e, g, i, j, and (±)-38 was carried out. It has been found that all the substrates with a benzyloxy group in the aryl moiety, regardless of its location, undergo oxidation at the 6-position preferentially as compared with the debenzyloxy derivatives such as (±)-4a, b. Comparison of the quantitative data from 4e and (±)-4f with those from (±)-4b indicated that the cis acetate chain at the 4-position increases the extent of the 6-oxidation, whereas a trans acetate chain at the same position has little effect. These two factors enhance the practical value of the "cincholoipon-incorporating method" for chiral syntheses of the 1-type Alangium alkaloids, in which the mercuric acetate-EDTA oxidation of 4e, g, i, j to the 6-piperidones (type 3)is one of the key synthetic operations. | |||||
| 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 | |||||
