FLAVAN DERIVATIVES .24. CIS- AND TRANS-3-METHOXYFLAVANONES

被引：30

作者：

CLARKLEWIS, JW

JEMISON, RW

NAIR, V

机构：

[1] The Blinders University of South Australia, Bedford Park SA

来源：

AUSTRALIAN JOURNAL OF CHEMISTRY | 1968年 / 21卷 / 12期

关键词：

D O I：

10.1071/CH9683015

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Oxidation of three 2, 3-cia-3, 4-cis-3-methoxyflavan-4-ols with active manganese dioxide gave the corresponding 2, 3-cis-3-methoxyflavanones which were equilibrated in deuterochloroform containing trifluoroacetic acid to mixtures of cis- (c.33%) and trans-3-methoxyflavanones (c.67%). Tominaga’s base-catalysed cyclization of 2′-hydroxy-α-methoxycha1cones to 3-methoxyflavanones has been found to yield the 2, 3-trans isomers. The higher stability of the 2, 3-trans-configuration of 3-hydroxy-flavanones (dihydroflavonols) compared with 3-methoxyflavanones is attributed to hydrogen bonding; no cis-isomer was detected when acid-catalysed epimerization of a trans-3-hydroxyflavanone was attempted. M.m.r. data are reported for the compounds described. © 1968 CSIRO. All rights reserved.

引用

页码：3015 / +

页数：1

共 56 条

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