4-O-丁香树脂酚合成工艺的改进  

Improved Synthesis of 4-O-syringaresinol

作　　者：陶凯奇 王红[1] 罗来春[1] 干国平[1] 彭小芝[1] 

机构地区：[1]湖北中医药大学药学院,湖北武汉430065

出　　处：《湖北中医药大学学报》2016年第6期51-53,共3页Journal of Hubei University of Chinese Medicine

基　　金：国家自然科学基金(项目编号:81274069)

摘　　要：目的对4-O-丁香树脂酚的合成工艺进行改进。方法以丁香醛为原料,与丙二酸进行Knovevenagel缩合得到芥子酸,再将芥子酸用乙醇进行乙酯化得到不饱和酯、以Al H(Bu-i)2为还原剂将酯还原为芥子醇、芥子醇在光照通入空气的条件下经过氧化偶联得4-O-丁香树脂酚。结果芥子酸的合成中,将催化剂哌啶换成相同碱性的四氢吡咯,在大幅度缩短反应时间的条件下,该步反应产率也明显提高;酯的还原中将溶解性较差的氢化锂铝换成溶解性好的二异丁基氢化铝,以甲苯为溶剂进行还原,收率明显提高,且无需后处理,可直接投入下一步反应,总收率约51%。结论该方法工艺简单,有产业化前景。Objective To improve the synthnesis of 4 -O- syringaresinol. Methods 4 -O -syringaresinol was synthesized from Syringaldehyde by Knovevenagel condensation with carboxyacetic acid, esterified by ethanol to get unsaturated ester, hydrogenated with AlH （Bu - i） 2 and osidative coupling by light and air to get 4 - O - syringaresinol. Results On the synthesis of sinapic acid, catalytic agent has been replaced by nafoxidine, which has the same alkalinity to piperidine. Not only the reaction time has been shorten significantly, but also reaction yield has been improved. On the reduction of unsaturated ester, as the reducing agent, Lithium aluminium hydride has been replaced by Diisobutylalnminium hydride, which get good solubility compared to Lithium aluminium hydride, reaction soultion has been replaced by toluene. Without complex afterprocessing, reduction yield has been improved remarkably. The reaction get an overll yield of 51%. Results This process was simple and suitable for industrialized preduction.

关 键 词：4-O-丁香树脂酚 合成 芥子酸 芥子醇 

分 类 号：R284.3[医药卫生—中药学]