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Structure–Activity Relationships in the Domain of Odorants Having Marine Notes
Author(s) -
Gaudin JeanMarc,
de Saint Laumer JeanYves
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201403365
Subject(s) - isoeugenol , chemistry , ketone , aldehyde , vanillin , ring (chemistry) , stereochemistry , organic chemistry , eugenol , catalysis
Continuing our investigations into marine note odorants, we herein describe several new scaffolds. Among them, 2,3‐dihydrobenzofuran‐2‐carbaldehyde is particularly interesting. The results demonstrate that the seven‐membered ring with a ketone functional group of the Calone 1951 ® family can be replaced by a five‐membered ring carrying an aldehyde function. In addition, this work has allowed us to discover the valuable 2‐methoxy‐4‐methylphenyl methyl carbonate ( 20b ), which is very close to vanillin, and 2‐methoxy‐2,4‐dimethyl‐1,3‐benzodioxole ( 29d ), which belongs to the isoeugenol/dihydroeugenol olfactive family.