酶催化Michael-aldol串联等反应合成三类杂环化合物

发布时间：2018-05-19 05:00

  本文选题：绿色化学 + 蛋白酶　； 参考：《东华理工大学》2017年硕士论文

【摘要】：杂环化合物,是一类具有生物活性和医学价值的有机化合物,近几年来对其合成方法的研究一直是人们关注的重点,引起科研者的极大兴趣,已报道的合成方法虽然高效,但部分不符合“绿色化学”,因此本论文研究绿色合成杂环化合物。主要研究工作有:(1)碱性蛋白酶催化Michael-aldol串联反应合成3-羟基-5-苯基四氢噻吩并[2,3-C]吡咯-4,6(5H)-2-酮。研究证实了碱性蛋白酶可以催化1,4-二硫-2,5-二醇与N-苯基马来酰亚胺发生Michael-aldol串联反应合成3-羟基-5-苯基四氢噻吩并[2,3-C]吡咯-4,6(5H)-2-酮。经过对酶的种类、溶剂以及温度的优化,得到了以去离子水为反应介质,在40℃温度下,碱性蛋白酶催化合成3-羟基-5-苯基四氢噻吩并[2,3-C]吡咯-4,6(5H)-2-酮,反应产率达到了93%,产物dr值为3:1。(2)蜂蜜曲霉蛋白酶催化2-甲基喹啉与芳醛亲核加成合成2-烷基氮杂芳烃类化合物。经过对酶的类型、溶剂、温度、酶量等的筛选,得到了合成2-烷基氮杂芳烃类化合物的绿色合成方法:60℃下,在50%甲醇与水(v/v)溶剂中,蜂蜜曲霉蛋白酶催化以2-甲基喹啉与2-硝基苯甲醛的模板反应,产率达到了60.4%;拓展了15种产物,最高产率达到了72%。(3)牛血清白蛋白催化合成黄烷酮类化合物。60℃下,在甲醇溶剂中,以牛血清白蛋白为催化剂,2'-羟基查尔酮自身环化合成黄烷酮类化合物,该反应取得了88.2%的高产率;拓展了7种产物,取得了40%-90%的产率。
[Abstract]:Heterocyclic compounds are a kind of organic compounds with biological activity and medical value. In recent years, the research on the synthetic methods of heterocyclic compounds has been the focus of attention, arousing great interest of researchers. However, some of them do not accord with "green chemistry", so this paper studies the green synthesis of heterocyclic compounds. The basic protease catalyzed Michael-aldol series reaction was used to synthesize 3-hydroxy-5-phenyltetrahydrothiopheno [2O3-C] pyrrole -4N ~ (6) H _ (5) H ~ (-)-(1) -ketone. The main works are as follows: (1) Alkaline protease catalyzes the series reaction of Michael-aldol. It has been proved that alkaline protease can catalyze the Michael-aldol series reaction of 1o 4-disulfide 5-diol with N-phenylmaleimide to synthesize 3-hydroxy-5-phenyl-tetrahydrothiopheno [2O3-C] pyrrole-4O6O5HnH-2-one. Based on the optimization of enzyme species, solvents and temperature, the synthesis of 3-hydroxy-5-phenyltetrahydrothiopheno [2O3-C] pyrrole-6na-5H ~ (-) -2-one with deionized water as the reaction medium was obtained by alkaline protease at 40 鈩，

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