Fluorinated musk fragrances : the CF2 group as a conformational bias influencing the odour of civetone and (R)-muscone
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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.
Callejo , R , Corr , M J , Yang , M , Wang , M , Cordes , D B , Slawin , A M Z & O'Hagan , D 2016 , ' Fluorinated musk fragrances : the CF 2 group as a conformational bias influencing the odour of civetone and ( R )-muscone ' Chemistry - A European Journal , vol 22 , no. 24 , pp. 8137-8151 . DOI: 10.1002/chem.201600519
Chemistry - A European Journal
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. This work is made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://dx.doi.org/10.1002/chem.201600519
This work was supported by the Engineering and Physical Sciences Research Council (EPSRC) and the European Research Council (ERC). The authors acknowledge the EPSRC National Mass Spectrometry Facility (Swansea). M.Y. thanks the China Scholarship Council for financial support. D.O'H. thanks the Royal Society for a Wolfson Research Merit Award.
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