1-(1,1,2,3,3,6-Hexamethyl-1,3-disilaindan-5-yl)ethanone (disila-phantolide, 4 ), a disila-analogue of the musk odorant phantolide ( 3 ), and its silicon-containing derivatives 5 − 13 were prepared in multistep syntheses and studied for their olfactory properties. In addition, 7 and 11 were structurally characterized by single-crystal X-ray diffraction, and compounds 4 − 13 were studied computationally (calculations of minimum-energy conformers and the electrostatic potentials). Compounds 4 − 13 differ in their Si−X−Si moiety (X = CHMe, C═CH 2, CH 2, O, cyclopropane-1,1-diyl) and in an optional C-6 methyl substituent on the 1,3-disilaindane skeleton. Disila-phantolide ( 4, X = CHMe), the methylene derivatives 6 and 7 (X = C═CH 2 ), and the cyclopropane-1,1-diyl derivatives 12 and 13 (X = cyclopropane-1,1-diyl) are new musk odorants, with 6 and 7 being the most interesting and powerful ones. In contrast, compounds 8 and 9 (X = CH 2 ) as well as 10 and 11 (X = O) were found to be very weak to odorless and devoid of any musk character.
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Metz et al. (2009) studied this question.