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Structure–Activity Relationship in the Domain of Odorants Having Marine Notes
Author(s) -
Gaudin JeanMarc,
Nikolaenko Olga,
de Saint Laumer JeanYves,
Winter Beat,
Blanc PierreAlain
Publication year - 2007
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200790126
Subject(s) - chemistry , substituent , ring (chemistry) , odor , stereochemistry , alkyl , table (database) , organic chemistry , database , computer science
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.