脱氢松香酸甲酯喹啉衍生物的合成与表征  

Synthesis and Characterization of Two Quinoline Derivatives from Dehydroabietic Acid

作　　者：张业[1] 潘英明[1] 王恒山[1] 陈清[1] 廖永志[1] 潘伟龙[1] 

机构地区：[1]广西师范大学化学化工学院,广西桂林541004

出　　处：《林产化学与工业》2007年第2期25-28,共4页Chemistry and Industry of Forest Products

基　　金：国家自然科学基金资助项目(20362002);广西高校百名中青年学科带头人资助计划资助项目(0229023);广西青年科学基金资助项目(0229023)

摘　　要：以脱氢松香酸甲酯(Ⅱ)为起始原料,通过在12位溴代得到12-溴-脱氢松香酸甲酯(Ⅲ),再经过在13位选择性硝化后还原制得中间体13-氨基脱异丙基脱氢松香酸甲酯(Ⅴ),Ⅴ继续与甘油在浓硫酸作用下缩合得(4R,12bS)-4,12b-二甲基-1,2,3,4,4a,5,6,12b-八氢化萘并[1,2-g]喹啉-4-羧酸甲酯(Ⅵ)和(7R,10aS)-7,10a-二甲基-5,6,6a,7,8,9,10,10a-八氢化萘并[2,1-f]喹啉-7-羧酸甲酯(Ⅶ)两种松香基喹啉衍生物,这两种产物的产率分别为51.2%和20.3%,质量分数分别为71.6%和28.4%,产物的结构通过IR,1HNMR和元素分析进行了表征。Two quinoline derivatives from dehydroabietic acid were synthesized. Methyl dehydroabietate （Ⅱ） was bromated at 12-position to give methyl 12-bromo-dehydroabiete （ Ⅲ ）. From Ⅲ, methyl 13-aminodeisopropyldehydroabietate （ Ⅴ ） was synthesized by nitration with nitric acid and hydrogenation in the presence of H2 and Pd/C. Then V was further converted into two quinoline derivatives, namely methyl （4R, 12bS）-4, 12b-dimethyl-1, 2, 3, 4, 4a, 5, 6, 12b-octahydronaphtho [ 1, 2-g] quinoline-4-carboxylate （Ⅵ） and methyl （7R, 10aS）-7, 10a-dimethyl-5, 6, 6a, 7, 8, 9, 10, 10a-octahydronaphtho [2, I-f] quinoline-7-carboxylate （Ⅶ）, by condensation with glycerol in the presence of concentrated sulfuric acid. The yields were 51.2 % and 20.3 % , and the mass fraction were 71.6 % and 28.4 % ,respectively. Their structurs were characterized by IR, ^1H NMR and elemental analysis.

关 键 词：脱氢松香酸甲酯 喹啉 

分 类 号：TQ351[化学工程]