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Structure–Activity Relationship in the Domain of Odorants Having Marine Notes

✍ Scribed by Jean-Marc Gaudin; Olga Nikolaenko; Jean-Yves de Saint Laumer; Beat Winter; Pierre-Alain Blanc

Publisher: John Wiley and Sons
Year: 2007
Tongue: German
Weight: 357 KB
Volume: 90
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.200790126

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✦ Synopsis

Abstract

We synthesized or re‐synthesized a large series of 2__H__‐1,5‐benzodioxepin‐3(4__H__)‐ones 9 (Scheme 1), 4,5‐dihydro‐1‐benzoxepin‐3(2__H__)‐ones 10 (Schemes 3 and 4) and 5,6,8,9‐tetrahydro‐7__H__‐benzocyclohepten‐7‐ones 11 (Schemes 5 and 6), since the lead compound for the olfactory note of perfumes based on marine accords is a well‐known benzodioxepinone named Calone 1951^®^ (9b). We meticulously described the odor profile of each synthesized compound and discussed relevant structure–odor relationships (Tables 1–3). In particular, we revealed a correlation between the conformation of the seven‐membered ring and the activities of these compounds (Table 4 and Fig. 3). We also clarified the effect of the position and the size of the alkyl substituent at the aromatic ring.

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