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首页> 外文期刊>Organometallics >5,6-Disubstituted 1,2,3-trisilaindanes as silicon analogues of phantolide-type musk odorants: Synthesis, structure, reactivity, and olfactory properties
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5,6-Disubstituted 1,2,3-trisilaindanes as silicon analogues of phantolide-type musk odorants: Synthesis, structure, reactivity, and olfactory properties

机译：5,6-二取代的1,2,3-三硅吲哚类化合物作为酚内酯型麝香加味剂的硅类似物：合成，结构，反应性和嗅觉特性

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摘要

In an extension of earlier studies concerning drugs and odorants based on disila-substituted tetrahydronaphthalene and indane skeletons, such as the musk odorant disila-phantolide (1), 1-(1,1,2,2,3,3,6-heptamethyl-1,2,3-trisilaindan- 5-yl)ethanone (methyltrisila-phantolide, 2) and a series of related 5,6-disubstituted 1,2,3-trisilaindanes (3-5) were prepared in multistep syntheses. Compounds 2-5 were characterized by ~1H, ~(11)B (5 only), ~(13)C, and ~(29)Si NMR studies. In addition, compounds 3-5 were studied by single-crystal X-ray diffraction. The 1,2,3-trisilaindane skeleton proved to have limited stability toward oxidation agents. The oxidation product 6, a novel 1,3,4-trisilaisochroman system, was isolated and characterized. The trisila-phantolide derivatives 2 and 3 do not display a typical musk odor, but instead possess a slightly creamy-lactonic odor with coumarinic aspects of very weak intensity (odor thresholds, >500 ng L ~(-1) air).
机译：在有关基于二硅烷基取代的四氢萘和茚满骨架的药物和加香剂的早期研究的扩展中，例如麝香加香剂二拉-甲萘酚（1），1-（1,1,2,2,3,3,6-七甲基通过多步合成法制备了-1,2,3-三硅双胍--5-基）乙酮（甲基三硅吡咯烷酮，2）和一系列相关的5,6-二取代的1,2,3-三硅氢化茚（3-5）。化合物2-5的特征是〜1H，〜（11）B（仅5个），〜（13）C和〜（29）Si NMR研究。另外，通过单晶X射线衍射研究了化合物3-5。 1,2,3-三硅茚满骨架对氧化剂的稳定性有限。分离并表征了氧化产物6，一种新颖的1,3,4-三硅异色满系统。 Trisila-phantolide衍生物2和3没有典型的麝香味，而是具有轻微的乳脂状气味，香豆素的强度很弱（气味阈值，> 500 ng L〜（-1）空气）。

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