Six‐Membered Silacycle Odorants: Synthesis and Olfactory Characterization of Si Analogues of Artemone, β‐Dynascone, and Herbac

Abstract

Abstract Si‐Artemone ( 4a ), Si‐β‐Dynascone ( 5a ), and Si‐Herbac 6a , which are Si analogues of the commercial fragrance ingredients Artemone ( 1 ), β‐Dynascone ( 2 ), and Herbac ( 3 ), were synthesized expediently by the insertion of terminal alkynes into silacyclobutane 7a . The sensory characterization results revealed that 4a and 6a had quite similar odor qualities compared with those of 1 and 3 , whereas 5a had a totally different odor character relative to that of 2 . In terms of the odor threshold values, that of 4a was slightly more substantive than that of its carbon analogue 1 , 6a was less potent than its carbon analogue 3 , whereas that of 5a was approximately one‐sixth that of its carbon analogue 2 .