title: Fluorinated Musk Fragrances: The CF2 Group as a Conformational Bias Influencing the Odour of Civetone and (R)-Muscone.
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.
authors.affiliation: School of Chemistry, University of St. Andrews, North Haugh, St. Andrews, KY16 9ST, UK.
authors.forename: Ricardo
authors.initials: R
authors.lastname: Callejo
authors.affiliation: School of Chemistry, University of St. Andrews, North Haugh, St. Andrews, KY16 9ST, UK.
authors.forename: Michael J
authors.initials: MJ
authors.lastname: Corr
authors.affiliation: School of Chemistry, University of St. Andrews, North Haugh, St. Andrews, KY16 9ST, UK.|Department of Applied Chemistry, College of Science, China Agricultural University, No.2 Yuanmingyuan West Road, Haidian District, Beijing, 100193, China.
authors.forename: Mingyan
authors.initials: M
authors.lastname: Yang
authors.affiliation: Department of Applied Chemistry, College of Science, China Agricultural University, No.2 Yuanmingyuan West Road, Haidian District, Beijing, 100193, China.
authors.forename: Mingan
authors.initials: M
authors.lastname: Wang
authors.affiliation: School of Chemistry, University of St. Andrews, North Haugh, St. Andrews, KY16 9ST, UK.
authors.forename: David B
authors.initials: DB
authors.lastname: Cordes
authors.affiliation: School of Chemistry, University of St. Andrews, North Haugh, St. Andrews, KY16 9ST, UK.
authors.forename: Alexandra M Z
authors.initials: AM
authors.lastname: Slawin
authors.affiliation: School of Chemistry, University of St. Andrews, North Haugh, St. Andrews, KY16 9ST, UK. do1@st-andrews.ac.uk.
authors.forename: David
authors.initials: D
authors.lastname: O'Hagan
mesh_terms: D018360:Crystallography, X-Ray; D003516:Cycloparaffins / Q000138:chemical synthesis / Q000737:chemistry*; D054879:Halogenation; D007536:Isomerism; D008968:Molecular Conformation; D009812:Odorants / Q000032:analysis; D010476:Perfume / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D003516:Cycloparaffins; D010476:Perfume; C056157:civetone; C031021:muscone
keywords: conformation analysis; macrocycles; musk fragrances; organofluorine chemistry; structure-activity relationships