2001年
Conformational analysis and selection of odor-active conformers: Synthesis of molecules designed for the Lily-of-the-Valley(Muguet)-type odor
HELVETICA CHIMICA ACTA
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- 巻
- 84
- 号
- 7
- 開始ページ
- 2051
- 終了ページ
- 2063
- 記述言語
- 英語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.1002/1522-2675(20010711)84:7<2051::AID-HLCA2051>3.0.CO;2-H
- 出版者・発行元
- WILEY-V C H VERLAG GMBH
The selection of odor-active conformers and the construction of a model for a targeted odor type, i.e., for the lily-of-the-valley odor, were examined. The disagreement of the odors of 1,3,4,5-tetrahydro-2-benzoxepin derivative 1 and 3-[4-(tert-butyl)phenyl]-2-methylpropanal (2) is discussed in terms of their stable conformers. The conformer active for the lily-of-the-valley odor was investigated by conformational analyses of several related compounds. Based on the integrated model consisting of the assumed active conformers (Fig. 5), compounds anticipated to possess the lily-of-the-valley odor were designed and synthesized. The odor of synthetic 7-(tert-butyl)-1,2,4,5-tetrahydro-3H-benzocyclohepten-3-one (8) and 3-[4-(tert-butyl)phenyl]cyclopentanone (13) were evaluated by perfumer, to have a floral odor and to recall the lily-of-the-valley anti lilac odors, respectively. Our methodology to design new odoriferous compounds. based on conformational analysis, selection of odor-active conformers, and construction of a model, proved to be satisfactory.
- リンク情報
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- DOI
- https://doi.org/10.1002/1522-2675(20010711)84:7<2051::AID-HLCA2051>3.0.CO;2-H
- Web of Science
- https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000170698300012&DestApp=WOS_CPL
- URL
- https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=0034861808&origin=inward
- ID情報
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- DOI : 10.1002/1522-2675(20010711)84:7<2051::AID-HLCA2051>3.0.CO;2-H
- ISSN : 0018-019X
- Web of Science ID : WOS:000170698300012