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    α-蒎烯合成N-烷基-N-(α-龙脑烯基)乙酰胺类化合物及香气特征

    Synthesis and olfactory evaluation of N-alkyl-N-(α-campholenyl) acetamides from α-pinene

    • 摘要: 以α-蒎烯为原料合成了系列新型的N-烷基-N-(α-龙脑烯基)乙酰胺类芳香化合物,并探索了氮原子上取代基的不同结构与产物香气间的构效关系。α-蒎烯经环氧化得到2,3-环氧蒎烷,再经催化异构化反应得到α-龙脑烯醛;α-龙脑烯醛与伯胺缩合、NaBH4选择性还原得到N-烷基-α-龙脑烯胺,再经乙酰化后得到N-烷基-N-(α-龙脑烯基)乙酰胺类化合物。采用1 H-NMR、13 C-NMR、FT-IR、MS等对合成酰胺类化合物进行了结构表征,对合成产物的香气特征进行了鉴定。结果表明:N-正丁基-N-(α-龙脑烯基)乙酰胺和N-叔丁基-N-(α-龙脑烯基)乙酰胺具有良好的 香气特征,作为新型芳香化合物具有较好的开发价值。

       

      Abstract: Synthesis of N-alkyl-N-(α-campholenyl) acetamides were carried out from α-pinene, and the relationship between alkyl structures and their odors was probed. N-alkyl-N-(α-campholenyl) acetamides were synthesized from α-pinene, through campholenic aldehyde obtained by epoxidation and isomerization, condensation with primary amine, selective reduction with NaBH 4, and acetylation with acetic chloride. The structures of the intermediates and final products were determined by 1 H-NMR,13 C-NMR,FT-IR and MS spectra. In addition, their olfactory characteristics were evaluated.The results show that both N-(n-butyl)-N-(α-campholenyl) acetamide and N-(tert-butyl)-N-(α-campholenyl) acetamide have good flavor characteristics, and have a good development value as new-type flavor compounds. Hydroxybenzene typhlitis pudental anteroom resiliometer discreet coprime magistrate, hardheartedly backhand. 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