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首页> 外文期刊>Organometallics >Disila-Phantolide and Derivatives: Synthesis and Olfactory Characterization of Silicon-Containing Derivatives of the Musk Odorant Phantolide
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Disila-Phantolide and Derivatives: Synthesis and Olfactory Characterization of Silicon-Containing Derivatives of the Musk Odorant Phantolide

机译:Disila-Phantolide及其衍生物:麝香气味Phantolide的含硅衍生物的合成和嗅觉表征

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摘要

1-(1,1,2,3,3,6-Hexamethyl-1,3-disilaindan-5-yl)ethanone (disila-phantolide, 4), a disila-analogue of the musk odorant phantolide (3), and its silicon-containing derivatives 5-13 were prepared in multistep syntheses and studied for their olfactory properties. In addition, 7 and 11 were structurally characterized by single-crystal X-ray diffraction, and compounds 4-13 were studied computationally (calculations of minimum-energy conformers and the electrostatic potentials). Compounds 4-13 differ in their Si-X-Si moiety (X = CHMe, C=CH2, CH2, O, cyclopropane-1,1-diyl) and in an optional C-6 methyl substituent on the 1,3-disilaindane skeleton. Disila-phantolide (4, X = CHMe), the methylene derivatives 6 and 7 (X = C=CH2), and the cyclopropane-1, 1-diyl derivatives 12 and 13 (X = cyclopropane-1,1-diyl) are new musk odorants, with 6 and 7 being the most interesting and powerful ones. In contrast, compounds 8 and 9 (X = CH2) as well as 10 and 11 (X = O) were found to be very weak to odorless and devoid of any musk character.
机译:1-(1,1,2,3,3,6-六甲基-1,3-二硅萘丹-5-基)乙酮(disila-phantolide,4),麝香气味的邻苯二酚(3)的diila-alogue,和它的含硅衍生物5-13是通过多步合成制备的,并对其嗅觉特性进行了研究。此外,通过单晶X射线衍射对7和11进行了结构表征,并对化合物4-13进行了计算研究(最小能量构象异构体和静电势的计算)。化合物4-13的Si-X-Si部分不同(X = CHMe,C = CH2,CH2,O,环丙烷-1,1-二基)和1,3-二硅氢化茚上的可选C-6甲基取代基骨架。二硅-甲基苯甲内酯(4,X = CHMe),亚甲基衍生物6和7(X = C = CH2),以及环丙烷-1、1-二基衍生物12和13(X =环丙烷-1,1-二基)新的麝香加味剂,其中6和7是最有趣且功能最强大的。相反,发现化合物8和9(X = CH2)以及化合物10和11(X = O)非常弱,无味,没有麝香。

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