Fluorinated musk fragrances: the CF2 group as a conformational bias influencing the odour of civetone and (R)-muscone

Ricardo Callejo, Michael J. Corr, Mingyan Yang, Mingan Wang, David B. Cordes, Alexandra M. Z. Slawin, David O'Hagan

Research output: Contribution to journalArticlepeer-review

17 Citations (Scopus)

Abstract

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.
Original languageEnglish
Pages (from-to)8137-8151
JournalChemistry - A European Journal
Volume22
Issue number24
Early online date6 May 2016
DOIs
Publication statusPublished - 6 Jun 2016

Keywords

  • Conformation analysis
  • Macrocycles
  • Musk fragrances
  • Organofluorine chemistry
  • Structure–activity relationships

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