3-羟基-β-二氢大马酮的合成及在线热裂解研究  

Synthesis of 3-hydroxy-β-damascone and its pyrolysis analysis

作　　者：李石头[1] 李山[1] 王莹莹[1] 贾春晓[1] 毛多斌[1] 

机构地区：[1]郑州轻工业学院烟草科学与工程学院,河南郑州450001

出　　处：《郑州轻工业学院学报（自然科学版）》2013年第2期64-68,共5页Journal of Zhengzhou University of Light Industry:Natural Science

摘　　要：对3-羟基-β-二氢大马酮的合成及在线热裂解进行了研究.以异亚丙基丙酮、乙酰乙酸乙酯为原料,经Michael加成和Robinson环合得到2,6,6-三甲基-4-氧代-2-环己烯-1-羧酸乙酯;再经乙二醇缩酮化、水解、NaBH4还原得到2,6,6-三甲基-4-羟基-1-环己烯-1-羧酸乙酯;最后经与烯丙基锂反应得到目标产物3-羟基-β-二氢大马酮.对目标产物结构进行了GC-MS,IR,LC-ESI-MS,1H NMR,13C NMR表征.在线热裂解GC-MS,分析结果表明,3-羟基-β-二氢大马酮在300℃基本不裂解,在600℃,750℃,900℃能裂解出β-大马酮、异佛尔酮等重要烟草香味物质.The synthetic technology of 3-hydroxy-β-damascone and its pyrolysis analysis were performed. Firstly ethyl 2,6,6-trimethyl-4-oxo-2- cyelohexene-l-carboxylate was obtained by reactions of Michael ad- dition and Robinson cyclation with mesityl oxide and ethyl acetoacetate as starting materials, then it was ke- talized with ethylene glycol, and was hydrolated and reduced by sodium borohydride to afford ethyl 2,6,6- trimethyl- 4-hydroxy- 1-cyclohexene-1- earboxylate , finally the obtained compound was coupled with allyl- lithium to give the title compound 3-hydroxy-β-damaseone. The structure of 3-hydroxy-β-damascone was charactered by GC-MS, IR, LC-ESI-MS, 1H NMR, and 13 C NMR. The pyrolysis results of 3-hydroxy-β-dam- ascone showed that it could hardly be pyrolyzed at 300 ℃, but could be pyrolyzed at 600℃, 750 ℃, 900℃ to produceβ-damascenone, isophorone, etc, which are important flavoring comopositions in tobacco.

关 键 词：3-羟基-β-二氢大马酮 合成 热裂解 

分 类 号：TQ655[化学工程—精细化工] TS264.3[轻工技术与工程—发酵工程]