3661-77-6Relevant articles and documents
Ruzicka,Huerbin,Furter
, p. 78,83 (1934)
Fluorinated Musk Fragrances: The CF2Group as a Conformational Bias Influencing the Odour of Civetone and (R)-Muscone
Callejo, Ricardo,Corr, Michael J.,Yang, Mingyan,Wang, Mingan,Cordes, David B.,Slawin, Alexandra M. Z.,O'Hagan, David
supporting information, p. 8137 - 8151 (2016/06/13)
The difluoromethylene (CF2) group has a strong tendency to adopt corner over edge locations in aliphatic macrocycles. In this study, the CF2group 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 CF2groups 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 CF2groups, lose their musk fragrance and become less pleasant.
A novel, short and repeatable two-carbon ring expansion reaction by thermo-isomerization: Easy synthesis of macrocyclic ketones
Nagel, Matthias,Hansen, Hans-Ju?rgen,Fra?ter, Georg
, p. 275 - 279 (2007/10/03)
A novel two-carbon ring enlargement procedure, in which medium- and large-ring 1-vinylcycloalkanols are thermoisomerized in a flow reactor system at temperatures of 600°C to about 650°C, produces the isomeric ring-expanded cycloalkanones directly and efficiently. This two-step ring expansion protocol can easily be applied several times successively. For e.g., the musk odorant cyclopentadecanone (Exaltone?) is prepared from cycloundecanone in two repetitive cycles. Thermo-isomerization of the corresponding ethynylic cycloalkanols gives in moderate yields the bishomologous α,β-unsaturated macrocyclic (E)-2-cycloalkenones. A reaction mechanism via alkyl hydroxyallyl biradical intermediates is proposed.
