Title: Conformational Analysis and Selection of Odor-Active Conformers: Synthesis of Molecules Designed for the Lily-of-the-Valley(Muguet)-Type Odor
Abstract: Helvetica Chimica ActaVolume 84, Issue 7 p. 2051-2063 Research Article Conformational Analysis and Selection of Odor-Active Conformers: Synthesis of Molecules Designed for the Lily-of-the-Valley(Muguet)-Type Odor Fumiko Yoshii, Fumiko Yoshii Graduate School of Science and Technology, Niigata University, 8050 Ikarashi 2 nocho, Niigata 950-2181, JapanSearch for more papers by this authorTomoko Nakamura, Tomoko Nakamura Faculty of Engineering, Niigata University, 8050 Ikarashi 2 nocho, Niigata 950-2181, JapanSearch for more papers by this authorShuichi Hirono, Shuichi Hirono Division of Physical Chemistry for Drug Design, School of Pharmaceutical Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo 108-0072, JapanSearch for more papers by this authorYumiko Shimizu, Yumiko Shimizu Faculty of Engineering, Niigata University, 8050 Ikarashi 2 nocho, Niigata 950-2181, JapanSearch for more papers by this authorTakashi Hoshi, Takashi Hoshi Faculty of Engineering, Niigata University, 8050 Ikarashi 2 nocho, Niigata 950-2181, JapanSearch for more papers by this authorMasayoshi Ando, Masayoshi Ando Faculty of Engineering, Niigata University, 8050 Ikarashi 2 nocho, Niigata 950-2181, JapanSearch for more papers by this authorHisahiro Hagiwara, Hisahiro Hagiwara Graduate School of Science and Technology, Niigata University, 8050 Ikarashi 2 nocho, Niigata 950-2181, JapanSearch for more papers by this author Fumiko Yoshii, Fumiko Yoshii Graduate School of Science and Technology, Niigata University, 8050 Ikarashi 2 nocho, Niigata 950-2181, JapanSearch for more papers by this authorTomoko Nakamura, Tomoko Nakamura Faculty of Engineering, Niigata University, 8050 Ikarashi 2 nocho, Niigata 950-2181, JapanSearch for more papers by this authorShuichi Hirono, Shuichi Hirono Division of Physical Chemistry for Drug Design, School of Pharmaceutical Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo 108-0072, JapanSearch for more papers by this authorYumiko Shimizu, Yumiko Shimizu Faculty of Engineering, Niigata University, 8050 Ikarashi 2 nocho, Niigata 950-2181, JapanSearch for more papers by this authorTakashi Hoshi, Takashi Hoshi Faculty of Engineering, Niigata University, 8050 Ikarashi 2 nocho, Niigata 950-2181, JapanSearch for more papers by this authorMasayoshi Ando, Masayoshi Ando Faculty of Engineering, Niigata University, 8050 Ikarashi 2 nocho, Niigata 950-2181, JapanSearch for more papers by this authorHisahiro Hagiwara, Hisahiro Hagiwara Graduate School of Science and Technology, Niigata University, 8050 Ikarashi 2 nocho, Niigata 950-2181, JapanSearch for more papers by this author First published: 20 August 2001 https://doi.org/10.1002/1522-2675(20010711)84:7<2051::AID-HLCA2051>3.0.CO;2-HCitations: 13AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Abstract 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 perfumers to have a floral odor and to recall the lily-of-the-valley and 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. Citing Literature Volume84, Issue7July 11, 2001Pages 2051-2063 RelatedInformation
Publication Year: 2001
Publication Date: 2001-07-11
Language: en
Type: article
Indexed In: ['crossref']
Access and Citation
Cited By Count: 16
AI Researcher Chatbot
Get quick answers to your questions about the article from our AI researcher chatbot