酶催化Michael-aldol串聯(lián)等反應(yīng)合成三類雜環(huán)化合物
發(fā)布時(shí)間:2018-05-19 05:00
本文選題:綠色化學(xué) + 蛋白酶; 參考:《東華理工大學(xué)》2017年碩士論文
【摘要】:雜環(huán)化合物,是一類具有生物活性和醫(yī)學(xué)價(jià)值的有機(jī)化合物,近幾年來對(duì)其合成方法的研究一直是人們關(guān)注的重點(diǎn),引起科研者的極大興趣,已報(bào)道的合成方法雖然高效,但部分不符合“綠色化學(xué)”,因此本論文研究綠色合成雜環(huán)化合物。主要研究工作有:(1)堿性蛋白酶催化Michael-aldol串聯(lián)反應(yīng)合成3-羥基-5-苯基四氫噻吩并[2,3-C]吡咯-4,6(5H)-2-酮。研究證實(shí)了堿性蛋白酶可以催化1,4-二硫-2,5-二醇與N-苯基馬來酰亞胺發(fā)生Michael-aldol串聯(lián)反應(yīng)合成3-羥基-5-苯基四氫噻吩并[2,3-C]吡咯-4,6(5H)-2-酮。經(jīng)過對(duì)酶的種類、溶劑以及溫度的優(yōu)化,得到了以去離子水為反應(yīng)介質(zhì),在40℃溫度下,堿性蛋白酶催化合成3-羥基-5-苯基四氫噻吩并[2,3-C]吡咯-4,6(5H)-2-酮,反應(yīng)產(chǎn)率達(dá)到了93%,產(chǎn)物dr值為3:1。(2)蜂蜜曲霉蛋白酶催化2-甲基喹啉與芳醛親核加成合成2-烷基氮雜芳烴類化合物。經(jīng)過對(duì)酶的類型、溶劑、溫度、酶量等的篩選,得到了合成2-烷基氮雜芳烴類化合物的綠色合成方法:60℃下,在50%甲醇與水(v/v)溶劑中,蜂蜜曲霉蛋白酶催化以2-甲基喹啉與2-硝基苯甲醛的模板反應(yīng),產(chǎn)率達(dá)到了60.4%;拓展了15種產(chǎn)物,最高產(chǎn)率達(dá)到了72%。(3)牛血清白蛋白催化合成黃烷酮類化合物。60℃下,在甲醇溶劑中,以牛血清白蛋白為催化劑,2'-羥基查爾酮自身環(huán)化合成黃烷酮類化合物,該反應(yīng)取得了88.2%的高產(chǎn)率;拓展了7種產(chǎn)物,取得了40%-90%的產(chǎn)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,
本文編號(hào):1908804
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