CONFIGURATION-ODOR RELATIONSHIPS IN 5-BETA-AMBROX

被引：36

作者：

ESCHER, S

GIERSCH, W

NICLASS, Y

BERNARDINELLI, G

OHLOFF, G

机构：

[1] FIRMENICH CO,RES LABS,CH-1211 GENEVA 8,SWITZERLAND

[2] UNIV GENEVA,CRYSTALLOG LAB,CH-1211 GENEVA 4,SWITZERLAND

来源：

HELVETICA CHIMICA ACTA | 1990年 / 73卷 / 07期

关键词：

D O I：

10.1002/hlca.19900730717

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The four possible A/B cis‐fused diastereoisomers of Ambrox® have been synthesized and their configurations and conformations established by X‐ray and NMR analysis. Only 5β‐ambrox (= 1,2,3a,4,5,5β,6,7,8,9,9a,9bα‐dodecahydro‐3aβ,6,6,9aβ‐tetramethylnaphtho[2,1‐b]furan; 5) has an odor quality comparable to Ambrox®. The 1,3‐synperiplanar/diaxial conformation of the substituents at C(8) ( = C(3a)) and C(10) (= C(9a)) has thus been confirmed to be a compulsory structure element for the particular odor. Copyright © 1990 Verlag GmbH & Co. KGaA, Weinheim

引用

页码：1935 / 1947

页数：13

共 23 条

[1] THE SYNTHESIS OF RACEMIC AMBROX [J].