3-羟基-1-(2,6,6-三甲基-3-环己烯基)-1-丁酮的合成及其向卷烟烟气释放δ-突厥酮的研究

Synthesis of 3-Hydroxy-1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-1- butanone and the Identification of Its Conversion to δ-Damascone in Tobacco Smoke

以亚异丙基丙酮 ,1 ,3 戊二烯为原料经Diels Alder反应合成了 4 乙酰基 3 ,5 ,5 三甲基环己烯 ( 4 ) ,4再与乙酸乙酯在乙醇钠的存在下缩合得到 1 ( 2 ,6,6 三甲基 3 环己烯 基 ) 1 ,3 丁二酮 ( 5 ) ,5用硼氢化钠还原合成了3 羟基 1 ( 2 ,6,6 三甲基 3 环己烯基 ) 1 丁酮。其结构经GC MS和1HNMR证实。将此目标化合物用作香料成分加入卷烟 ,用GC MS检测其烟气成分 ,发现此化合物在卷烟燃吸时能发生裂解反应 ,向烟气释放具有致香作用的δ 突厥酮。

3-Hydroxy-1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-1-butanone, a important precursor of δ-damascone, was synthesized and characterized by GC-MS and 1H NMR. The title compound was prepared by Diels-Alder cycloaddition of penta-1,3-diene and mesityl oxide, condensation of the cycloaddition with ethyl acetate and the reduction of the condensation products with sodium borohydride. The title compound was used as a perfume additive in cigarette composition. It was found that the title compound could be pyrolyzed to produce δ-damascone in tobacco smoke upon smoking.