期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2016, 期 5, 页码 976-982出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201501338
关键词
Fragrances; Silicon; Silanes; Molecular modeling; Structure-activity relationships
资金
- National Natural Science Foundation of China (NSFC) [21102178, 21402239]
A series of silicon-containing derivatives of linear alicyclic musks comprising sila-Rosamusk (3b), sila-Romandolide (5b), sila-Applelide (11b), and the corresponding dehydro derivatives was synthesized from sila-analogs of Artemone and Herbac, respectively, by means of sodium borohydride reduction and subsequent esterification with the corresponding acid chlorides in the presence of triethylamine. The olfactory properties of the new sila-odorants 3b-13b are reported in comparison with their carba-analogs 3a-13a, and quantitative threshold data allowed the generation of an improved musk olfactophore model featuring a correlation of 80.5% with a null-cost distance of 244. This olfactophore model shows that it is likely that linear and macrocyclic musks address the same odorant receptors, and it should facilitate the design of new musks.
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