Fluorinated Musk Fragrances: The CF2 Group as a Conformational Bias Influencing the Odour of Civetone and (R)‐Muscone,Chemistry - A European Journal

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Fluorinated Musk Fragrances: The CF2 Group as a Conformational Bias Influencing the Odour of Civetone and (R)‐Muscone
Chemistry - A European Journal ( IF 3.9 ) Pub Date : 2016-05-06 , DOI: 10.1002/chem.201600519
Ricardo Callejo ₁ , Michael J. Corr ₁ , Mingyan Yang _{1,

2} , Mingan Wang ₂ , David B. Cordes ₁ , Alexandra M. Z. Slawin ₁ , David O'Hagan ₁

Affiliation

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.

中文翻译：

氟化麝香香气：CF2组作为影响西维酮和（R）-Muscone气味的构象偏见

二氟亚甲基（CF ₂）基团在脂族大环化合物中具有在边缘位置转角的强烈趋势。在这项研究中，CF ₂基已被引入到麝香相关的大环酮中。通过合成制备了九个西维酮和五个麝香酮类似物，用于结构和气味比较。X射线研究确实表明，CF ₂基团会影响环的结构，并且使他们对首选的环构型有一些了解，从而触发了在专业香水环境中确定的麝香味。Bersuker及其同事对麝香香精的历史构象模型通常保持不变，并且由于CF ₂的特殊放置而使结构偏离了这一共识。群体，失去麝香的香味，变得不那么愉快。

更新日期：2016-05-06

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