12-(2,4-二硝基苯腙基)-8-羟基-7,8-二氢枞酸及其甲酯的合成及表征  

Synthesis and structure characterization of 12-(2,4-dinitro-phenylhydrazono)-8-hydroxy-7,8-dihydroabietic acid and its methyl ester

作　　者：黄道战[1,2] 蓝虹云[2] 蓝洁[2] 钟亚萍[2] 雷福厚 曾韬[1] 

机构地区：[1]南京林业大学化学工程学院,江苏南京210037 [2]广西民族大学化学与生态工程学院,广西南宁530006

出　　处：《南京林业大学学报（自然科学版）》2010年第3期20-24,共5页Journal of Nanjing Forestry University：Natural Sciences Edition

基　　金：广西青年科学基金项目(桂科青0728016);广西林产化学品开发与应用重点实验室开放基金项目(GXFC0813);广西高校松香系列新产品开发人才小高地开放基金项目

摘　　要：利用松脂制备的2-氨基-2-甲基丙醇左旋海松酸盐进行光敏氧化反应,合成左旋海松酸跨环过氧化物丁醇胺盐,经酸化、异构化、酯化等步骤得到12-羰基-8-羟基-7,8-二氢枞酸(5a)及其甲酯(5b);研究5a和5b与2,4-二硝基苯肼的缩合反应,利用紫外-可见吸收光谱、红外吸收光谱、元素分析仪、1H和13C核磁共振谱对反应产物进行结构表征。结果表明,在浓硫酸催化作用下,5a和5b与2,4-二硝基苯肼发生缩合反应,生成新的化合物12-(2,4-二硝基苯腙基)-8-羟基-7,8-二氢枞酸(6a)及其甲酯(6b);6a和6b存在一个较大π电子共轭体系,其分子结构较稳定。12-carboxy-8-hydroxy -7,8-dihydroabietic acid （5a） and its methyl ester （5b） was prepared through several steps,including acidification,isomerization and esterification,of 2-amino-2-methyl-1-propanol salt of levopimaric acid transannular peroxide,which was obtained from directly photo-sensitized oxidation reaction of 2-amino-2-methyl-1-propanol salt of levopimaric acid isolated from pine oleoresin. The reaction of 5a and 5b with 2,4-dinitrophenyl hydrazine were investigated,and then the products were characterized by means of UV,IR,1H NMR,13C NMR,and elemental analysis. The experimental results showed that the new compounds 12-（2,4-dinitro-phenylhydrazono）-8-hydroxy-7,8-dihydroabietic acid （6a） and its methyl ester （6b）,which have an extensive π electron conjugation and structural stability,were synthesized by a condensation reaction of 5a and 5b with 2,4-dinitrophenyl hydrazine by using concentrated sulfuric acid as catalyst.

关 键 词：12-羰基-8-羟基-7 8-二氢枞酸 苯腙 合成 结构表征 

分 类 号：TQ630.4[化学工程—精细化工]