三联吡啶衍生物合成与分析教学实践  

Teaching Practice for Synthesis and Analysis of Terpyridine Derivative

作　　者：欧植泽[1] 钱一梦 高云燕[1] 刘光汉[1] 姜恺悦 雷晶[1] 

机构地区：[1]西北工业大学理学院,陕西西安710072

出　　处：《实验室研究与探索》2016年第7期173-178,共6页Research and Exploration In Laboratory

基　　金：国家自然科学基金(21073143);2015-2016年度西北工业大学教学与考核模式改革课程项目;西北工业大学创新训练项目(201510699217)

摘　　要：4-(对甲苯基)-2,2':6',2″-三联吡啶(ttpy)的合成包括羟醛缩合反应,1,4-共轭加成反应和羰基的亲核加成等反应。将ttpy的合成开发成本科生有机化学教学实验,有助于学生进一步了解醛酮化合物的性质以及羟醛缩合反应和1,4-共轭加成等反应的机理。本实验以2-乙酰吡啶和对甲基苯甲醛为原料,对反应溶剂、Na OH浓度和反应温度等条件进行优化,提高了羟醛缩合反应的产率(95.7%)。在KOH存在条件下,羟醛缩合反应产物3-(4-甲基苯基)-1-(2-吡啶基)-2-丙烯-1-酮进一步与氨水反应,得到4-(对甲苯基)-2,2':6',2″-三联吡啶。在最优化条件下,两步反应合成4-(对甲苯基)-2,2':6',2″-三联吡啶的总产率可达65.8%。运用红外吸收光谱(IR)和核磁共振氢谱(1H NMR)对化合物的结构表征。The synthesis of terpyridine （npy） includes aldol condensation, 1,4-conjugate addition and carbonyl nucleophilic addition. Applying the synthesis of the ttpy in organic experiment teaching for undergraduate students will be helpful for the students to understand the properties of carbonyl compounds and the mechanism of the above reactions. 3-（4-methylphenyl）-1-（pyridin-3-yl） prop-2-en-1-one is prepared by aldol condensation of 2-acetylpyridine and 4- methylbenzaldehyde. The reaction conditions, including solvent, concentration of NaOH and reaction temperature are optimized, and result in good yield. Further reaction of 3-（4-methylphenyl）-1-（pyridiu-3-yl） prop-2-en-l-one with concentrated ammonia in the presence of KOH gives 4＇-p-tolyl-2,2＇ ： 6＇,2＂-terpyridine. The final product 4＇-p-tolyl-2, 2＇ ：6＇ ,2＂-terpyridine can be obtained with an overall yield up to 65.8%. The mechanisms of the aldol condensation reaction and 1,4-conjugate addition reaction are also studied. The reaction products are characterized by using ^1H NMR and IR spectra.

关 键 词：羟醛缩合反应 Α Β-不饱和酮 1 4-共轭加成反应 三联吡啶合成 

分 类 号：O622.4[理学—有机化学] G642.0[理学—化学]