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Fluorinated Musk Fragrances: The CF 2 Group as a Conformational Bias Influencing the Odour of Civetone and ( R )‐Muscone
Author(s) -
Callejo Ricardo,
Corr Michael J.,
Yang Mingyan,
Wang Mingan,
Cordes David B.,
Slawin Alexandra M. Z.,
O'Hagan David
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201600519
Subject(s) - ring (chemistry) , chemistry , stereochemistry , group (periodic table) , organic chemistry
The difluoromethylene (CF 2 ) group has a strong tendency to adopt corner over edge locations in aliphatic macrocycles. In this study, the CF 2 group has been introduced into musk relevant macrocyclic ketones. Nine civetone and five muscone analogues have been prepared by synthesis for structure and odour comparisons. X‐ray studies indeed show that the CF 2 groups influence ring structure and they give some insight into the preferred ring conformations, triggering a musk odour as determined in a professional perfumery environment. The historical conformational model of Bersuker and co‐workers for musk fragrance generally holds, and structures that become distorted from this consensus, by the particular placement of the CF 2 groups, lose their musk fragrance and become less pleasant.