Synthesis and Olfactory Characterization of Sila-Methyl Pamplemousse and Related Odorants with a 2,2,5-Trimethyl-2-silahex-4-ene Skeleton

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• 作者：Julian Friedrich ; Steffen D?rrich ; André Berkefeld ; Philip Kraft ; Reinhold Tacke
• 刊名：Organometallics
• 出版年：2014
• 出版时间：February 10, 2014
• 年：2014
• 卷：33
• 期：3
• 页码：796-803
• 全文大小：289K
• ISSN：1520-6041

文摘

The synthetic grapefruit odorant methyl pamplemousse (1a) has lately become an important trend odorant, and the related 2,2,5-trimethylhex-4-enes 2a鈥?b>4a also possess interesting olfactory properties of fresh hesperidic and fruity-agrestic character. On the basis of the carbon/silicon switch strategy, the silicon-containing analogues sila-methyl pamplemousse (1b) and 2b鈥?b>4b were synthesized and studied for their olfactory properties (olfactory evaluation of the C/Si pairs 1a/1b鈥?b>4a/4b). Sila substitution (C/Si exchange) was demonstrated to affect the olfactory properties substantially. The C/Si analogues 1a and 1b were found to be genuine grapefruit odorants, with the silicon compound 1b showing additional agrestic facets. As a proof of principle, it was demonstrated that C/Si analogues can display a different mechanism and rate of degradation (degradation studies with 1a and 1b under acidic conditions).