两种脱氢松香基喹啉衍生物的合成与表征  

Synthesis and Characterization of Two Quinolines from Dehydroabietic Acid

作　　者：童碧海[1] 农容丰[2] 王恒山[1] 潘英明[1] 卢昕[1] 

机构地区：[1]广西师范大学化学化工学院,广西桂林541004 [2]南宁师范高等专科学校化学系,广西龙州532400

出　　处：《精细化工》2005年第5期398-400,共3页Fine Chemicals

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

摘　　要：以脱氢松香酸为原料,用硫酸二甲酯酯化后,再在苯和无水三氯化铝作用下脱除异丙基,制得顺式脱异丙基化脱氢松香酸甲酯(Ⅲ),Ⅲ再经12位硝化、还原后制得中间体顺式12 氨基脱烷基化脱氢松香酸甲酯(Ⅴ),Ⅴ继续与甘油在浓硫酸作用下缩合得(4R, 4aR, 4bR) 4, 12b 二甲基1, 2, 3, 4, 4a, 5, 6, 12b 八氢化萘并[2, 1 g]喹啉4 羧酸甲酯(Ⅵ)和(8aR, 9R, 12aR) 9, 12a 二甲基7, 8, 8a, 9, 10, 11, 12, 12a 八氢化萘并[1, 2 f]喹啉9 羧酸甲酯(Ⅶ)两种松香基喹啉衍生物,这两种产物的质量分数分别为73 5%和26 5%,产物的结构通过IR,MS,1HNMR进行了表征。Starting from dehydroabietic acid,methyl cis-deisopropyldehydroabietate(Ⅲ) was synthesized by esterification with (Me)_2SO_4 and deisopropylation in the presence of anhydrous AlCl_3/benzene.Then Ⅲ was nitrated at the 12-position and reduced to methyl cis-12-aminodeisopropyldehydroabietate(Ⅴ).Ⅴ was further converted into two quinolines,methyl (4R,4aR,12bR)-4,12b-dimethyl-1,2,3,4,4a,5,6,12b-octahydronaphtho[2,1-g]quinoline-4-carboxylate and methyl (4R,4aR,12bR)-4,12b-dimethyl-7,8,8a,9,10,11,12,12a-octahydronaphtho[1,2-f]quinoline-9-carboxylate,by condensation with glycerol in the presence of concentrated sulfuric acid.Two products were produced in mass percents of 73.5% and 26.5% respectively.The compositions and structures were characterized by IR,~1HNMR and MS.

关 键 词：脱氢松香酸 酯化 喹啉 

分 类 号：O626[理学—有机化学]