期刊
CHEMISTRY & BIODIVERSITY
卷 11, 期 10, 页码 1651-1673出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cbdv.201400072
关键词
Muguet; Odorants; Claisen rearrangement; Sila substitution; Structureodor relationship (SOR)
A series of Claisen rearrangements was undertaken in order to find a replacement for Lilial (=3-(4-(tert-butyl)phenyl)-2-methylpropanal), a high-tonnage perfumery ingredient with a lily-of-the-valley odour, which is a CMR2 material [1]. 5,7,7-Trimethyl-4-methyleneoctanal (10), the synthesis of which is described, became the main lead. It possesses an odour which is very close to that of Lilial but lacks its substantivity. Aldehydes with higher molecular weights than that of 10 were, therefore, synthesised in order to boost substantivity and to understand the structural requirements for a Lilial' odour. The aldehydes were obtained via Claisen rearrangements of exo-methylidene' vinyl ethers, allenyl vinyl ethers, or allenyl allyl ethers. Alternatively, coupling of terminal alkynes with allyl alcohols led to the desired aldehydes. Derivatives of 10 and their sila analogues were also synthesised. The olfactory properties of all synthesised molecules were evaluated for possible structureodour relationships (SOR).
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据