z-logo
Premium
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).

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here