2525-09-9Relevant academic research and scientific papers
Conception, characterization and correlation of new marine odorants
Kraft, Philip,Eichenberger, Walter
, p. 3735 - 3743 (2007/10/03)
Via a synthetic sequence consisting of PPA-mediated Friedel-Crafts acylation of veratrol (8), Clemmensen reduction, demethylation with TMSI, Williamson ether synthesis employing 3-chloro-2-(chloromethyl)prop-1-ene and in-situ ruthenium tetroxide oxidation, numerous substituted benzo[b][1,4]dioxepinones 15-27 and 2,3-dihydro-1H-5,9-di-oxacyclohepta[f]indenones 7, 13 and 14 were prepared to study their odor-structure correlation. In the course of these studies, we discovered the extremely powerful new marine odorant 7-(3′ -methylbutyl)benzo[b][1,4]dioxepin-3-one (16). On the basis of the measured odor threshold data, an olfactophore model was constructed that rationalizes the observed odor intensities, and indicates an aliphatic hydrophobe at a distance of 6.3 A from the centre of the aromatic-ring binding site. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
