Fluorinated Musk Fragrances: The CF2 Group as a Conformational Bias Influencing the Odour of Civetone and (R)-Muscone

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• 作者：Dr. Ricardo Callejo ; Dr. Michael J. Corr ; Mingyan Yang ; Prof. Mingan Wang ; Dr. David B. Cordes ; Prof. Alexandra M. Z. Slawin and Prof. David O' ; Hagan
• 刊名：Chemistry - A European Journal
• 出版年：2016
• 出版时间：June 6, 2016
• 年：2016
• 卷：22
• 期：24
• 页码：8137-8151
• 全文大小：3082K
• ISSN：1521-3765

文摘

The difluoromethylene (CF₂) group has a strong tendency to adopt corner over edge locations in aliphatic macrocycles. In this study, the CF₂ 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 CF₂ 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 CF₂ groups, lose their musk fragrance and become less pleasant.