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

We synthesized or re‐synthesized a large series of 2H‐1,5‐benzodioxepin‐3(4H)‐ones 9 (Scheme 1), 4,5‐dihydro‐1‐benzoxepin‐3(2H)‐ones 10 (Schemes 3 and 4) and 5,6,8,9‐tetrahydro‐7H‐benzocyclohepten‐7‐ones 11 (Schemes 5 and 6), since the lead compound for the olfactory note of perfumes based on marine...

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Bibliographic Details
Published in:Helvetica chimica acta 2007-07, Vol.90 (7), p.1245-1265
Main Authors: Gaudin, Jean-Marc, Nikolaenko, Olga, de Saint Laumer, Jean-Yves, Winter, Beat, Blanc, Pierre-Alain
Format: Article
Language:English
Subjects:
Benzodioxepinones
Benzoxepin-3(4H)-ones
Calone 1951
Odorants
Structure-activity relationships
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Summary:We synthesized or re‐synthesized a large series of 2H‐1,5‐benzodioxepin‐3(4H)‐ones 9 (Scheme 1), 4,5‐dihydro‐1‐benzoxepin‐3(2H)‐ones 10 (Schemes 3 and 4) and 5,6,8,9‐tetrahydro‐7H‐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.
ISSN:0018-019X
1522-2675
DOI:10.1002/hlca.200790126