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

doi:10.3969/j.jssn.1000-2006.2010.03.005

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南京林业大学学报（自然科学版） ›› 2010, Vol. 34 ›› Issue (03): 20-24.doi: 10.3969/j.jssn.1000-2006.2010.03.005

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

黄道战¹,²,蓝虹云²,蓝洁²,钟亚萍²,雷福厚²,曾韬¹*

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

出版日期:2010-06-29 发布日期:2010-06-29

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

HUANG Daozhan¹,², LAN Hongyun², LAN Jie², ZHONG Yaping², LEI Fuhou², ZENG Tao¹*

1.College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China; 2.College of Chemistry and Ecological Engineering, Guangxi University for Nationalities, Nanning 530006, China

Online:2010-06-29 Published:2010-06-29

摘要/Abstract

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。

Abstract: 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.

中图分类号:

TQ630.4

黄道战,蓝虹云,蓝洁,等. 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[J]. 南京林业大学学报（自然科学版）, 2010, 34(03): 20-24.

HUANG Daozhan,, LAN Hongyun, LAN Jie, ZHONG Yaping, LEI Fuhou, ZENG Tao*. Synthesis and structure characterization of 12(2,4dinitrophenylhydrazono) 8hydroxy7,8dihydroabietic acid and its methyl ester[J].Journal of Nanjing Forestry University (Natural Science Edition), 2010, 34(03): 20-24.DOI: 10.3969/j.jssn.1000-2006.2010.03.005.

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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

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