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Structure-Odor Correlation, XXIV. Synthesis and Olfactory Properties of Damascone and Damascenone Analogs

✍ Scribed by Weyerstahl, Peter ;Licha, Kai

Publisher
John Wiley and Sons
Year
2006
Tongue
English
Weight
595 KB
Volume
1996
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

The aldehydes rac‐1, rac‐2, and 3 were conveniently prepared by starting from isophorone (4). Reaction of 1–3 with (E,Z)‐1‐bromo‐1‐propene (14) afforded the rac‐allylic alcohols (E,Z)‐15, ‐18, and ‐20. The alcohols were oxidized to the damascone/damascenone analogs 1‐(3,5,5‐trimethyl‐2‐cyclohexen‐1‐yl)‐ (rac‐16), 1‐(3,5,5‐trimethyl‐1‐cyclohexen‐1‐yl)‐ (rac‐19), and 1‐(3,5,5‐trimethyl‐1,3‐cyclohexadien‐1‐yl)‐2‐buten‐1‐one (21), and the (E/Z) isomers were separated by FC. Their olfactory evaluation shows that the highly estimated odor of damascone (A, B) and damascenone (C) is more or less lost. This result can be explained by force‐field calculation of the lowest energy conformation of 16, 19, and 21 in comparison with those of A–C.

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