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Synthesis of 1,3,4,5‐Tetrahydro‐2‐benzoxepin Derivatives as Conformationally Restricted Analogues of cyclamenaldehyde‐type compounds and as intermediates for highly odour‐active homologues
Author(s) -
Skouroumounis Georges,
Winter Béat
Publication year - 1996
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.19960790418
Subject(s) - chemistry , substituent , stereochemistry , ring (chemistry) , side chain , organic chemistry , polymer
Nine 1,3,4,5‐tetrahydro‐2‐benzoxepin derivatives have been prepared as mimics of the folded ( gauche ) conformation of cyclamenaldehyde ( 1 ) and related compounds, but none of them showed the typical lily‐of‐the valley (muguet) odour activity. However, conversion of these substances to previously unknown analogues of 1 having a Me substituent on the aromatic ring in an ortho position to the side chain led to new fragrance substances with remarkable properties. The results indicate that the extended ( anti ) conformation is more likely to be the ‘bioactive’ one at the receptor site(s).