Synthesis and olfactory characterization of silicon-containing derivatives of the acyclic lily-of-the-valley odorant 5,7,7-trimethyl-4-methylideneoctanal

Abstract

5-Methyl-4-methylidene-6-(trimethylsilyl)hexanal (1b), a sila analog of the acyclic lily-of-the-valley odorant 5,7,7-trimethyl-4-methylideneoctanal (1a), and the Si-containing derivatives 2-6 were prepared in multistep syntheses, starting from Cl3SiH and Cl2SiMe2 , respectively. Compounds 1b, 2-6, and their new precursors were characterized by elemental analyses (C, H, N) and NMR spectroscopic studies (1H, 13C, 15N, and 29Si). To gain more information about the structure-odor correlation in the family of lily-of-the-valley or muguet odorants, C/Si analogs 1a/1b and derivatives 2-6 were evaluated for their olfactory properties.