Synthesis and Olfactory Properties of Silicon‐Containing Analogs of Rosamusk, Romandolide, and Applelide: Insights into the Structural Parameters of Linear Alicyclic Musks
Synthesis and Olfactory Properties of Silicon‐Containing Analogs of Rosamusk, Romandolide, and Applelide: Insights into the Structural Parameters of Linear Alicyclic Musks
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DOI：
10.1002/ejoc.201501338
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发表时间：
2016-02
影响因子：
2.8
通讯作者：
Junhui Liu;Y. Zou;W. Fan;Jian Mao;Guobi Chai;Peng Li;Zhan Qu;Yongli Zong;Jianxun Zhang
中科院分区：
文献类型：
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作者：
Junhui Liu;Y. Zou;W. Fan;Jian Mao;Guobi Chai;Peng Li;Zhan Qu;Yongli Zong;Jianxun Zhang
以青蒿酮和Herbac的Sila类似物为原料，通过硼氢化钠还原和相应的酸氯化物在三乙胺存在下的酯化反应，合成了一系列含硅的线性脂环麝香的衍生物，包括Sila-Rosamusk(3b)，Sila-Romandolide(5b)，Sila-Applelide(11b)，以及相应的脱水衍生物。报告了新的Sila香味剂3b-13b的嗅觉特性，并与它们的Carba类似物3a-13a进行了比较，定量阈值数据允许生成一个改进的麝香嗅觉模型，其相关性为80.5%，零成本距离为244。这个嗅觉模型表明，线性麝香和大环麝香很可能处理相同的气味感受器，这应该有助于新麝香的设计。
A series of silicon-containing derivatives of linear alicyclic musks comprising sila-Rosamusk (3b), sila-Romandolide (5b), sila-Applelide (11b), and the corresponding dehydro derivatives was synthesized from sila-analogs of Artemone and Herbac, respectively, by means of sodium borohydride reduction and subsequent esterification with the corresponding acid chlorides in the presence of triethylamine. The olfactory properties of the new sila-odorants 3b–13b are reported in comparison with their carba-analogs 3a–13a, and quantitative threshold data allowed the generation of an improved musk olfactophore model featuring a correlation of 80.5 % with a null-cost distance of 244. This olfactophore model shows that it is likely that linear and macrocyclic musks address the same odorant receptors, and it should facilitate the design of new musks.