本文選題：含氮雜環(huán)化合物 + 氮雜環(huán)卡賓��； 參考：《貴州大學》2017年碩士論文

【摘要】：含氮雜環(huán)化合物作為有機合成領域的重要合成單元,常見于天然產(chǎn)物、材料、醫(yī)藥及農(nóng)藥分子骨架中,由于其獨特的生物活性引起了有機合成領域的高度重視,如何利用高效、簡潔的合成策略構建含氮雜環(huán)類化合物一直是本領域域的研究熱點和難點。吲哚類化合物是含氮雜環(huán)化合物中的重要一員,其高效的生物活性已被深入研究并得到了廣泛的應用。如何實現(xiàn)含吲哚類骨架化合物的精修并合成出結構新穎的吲哚類衍生物一直是有機合成領域的熱點。有機小分子催化劑是近年來有機催化領域的研究重點之一,氮雜環(huán)卡賓作為有機小分子催化劑中的后起之秀由于其獨特的催化活化模式受到了科研人員的深入研究并得到了迅速發(fā)展。羰基類化合物的?-位活化是氮雜化卡賓催化領域的重要活化模式之一。因此本論文主要研究了氮雜環(huán)卡賓催化吲哚芳雜醛的支鏈γ-位sp3碳原子的活化,構建結構新穎的吲哚衍生物及其生物活性研究等兩個方面的內(nèi)容。1.在氮雜環(huán)卡賓催化劑和聯(lián)苯二醌氧化劑的作用下,催化氧化3-甲基-2-吲哚醛的sp3碳原子活化,形成環(huán)外雙烯醇式中間體與三氟苯乙酮反應,以氧雜Diels-Alder環(huán)加成方式反應,在室溫條下,以高的收率一步構建含有六元環(huán)內(nèi)酯、季碳中心、三氟甲基以吲哚為主要骨架的螺環(huán)化合物。此方法以高效簡潔的方式,實現(xiàn)吲哚類化合物的多官能團化,合成出結構新穎的吲哚衍生物,并成功實現(xiàn)了吲哚這類芳雜醛環(huán)外碳原子的活化,為芳醛γ-位碳原子的活化提供理論依據(jù)。2.通過使用濁度法,對已合成出的部分目標化合物,進行生物活性測試,發(fā)現(xiàn)化合物3p在濃度為200和100μg/m L時對水稻白葉枯細菌的抑制率均為100%,其他化合物對這兩種植物細菌抑菌活性較差。
[Abstract]:As an important synthetic unit in the field of organic synthesis, nitrogen-containing heterocyclic compounds are commonly used in natural products, materials, medicine and pesticide molecular skeletons. Because of their unique biological activities, they have attracted great attention in the field of organic synthesis. The construction of heterocyclic compounds containing nitrogen by simple synthesis strategy has been a hotspot and difficulty in this field. Indole compounds are important members of nitrogen-containing heterocyclic compounds, and their highly effective biological activities have been deeply studied and widely used. How to refine the indole skeleton compounds and synthesize novel indole derivatives has been a hotspot in the field of organic synthesis. In recent years, small organic catalyst is one of the most important research fields in the field of organic catalysis. Nitrogen heterocyclic carbene as a rising star of organic small molecule catalysts has been deeply studied and developed rapidly because of its unique catalytic activation mode. The activation of carbonyl compounds is one of the most important activation modes in the field of nitrogen hybrid carbene catalysis. In this thesis, the activation of 緯-sp3 carbon atom in the branched chain of indole aromatic aldehyde catalyzed by carbene was studied, and two novel indole-derived derivatives were constructed and their biological activities were studied. The sp3 carbon atom of 3-methyl-2-indolaldehyde was activated by the catalytic oxidation of 3-methyl-2-indolaldehyde under the action of aza-heterocyclic carbene catalyst and biquinone oxidant, which formed an extracyclic dienol intermediate reacting with trifluoroacetophenone. The reaction was carried out in the form of oxygen-heterocyclic Diels-Alder cycloaddition. At room temperature, the spirocyclic compounds containing hexachlorolactone, quaternary carbon center and indole-like backbone of trifluoromethyl were synthesized in one step with high yield. In this method, the multi-functional group of indole compounds was realized, and the novel indole derivatives were synthesized, and the activation of carbon atoms outside the ring of aromatic aldehydes such as indole was successfully realized. It provides a theoretical basis for the activation of aromatic aldehydes 緯 -site carbon atom. By using the turbidimetric method, the bioactivity of some of the target compounds has been tested. It was found that the inhibition rate of compound 3p to rice white leaf blight bacteria was 100 at the concentrations of 200 and 100 渭 g / mL, while the other compounds had poor antibacterial activity against these two plant bacteria.
【學位授予單位】：貴州大學
【學位級別】：碩士
【學位授予年份】：2017
【分類號】：O626

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本文編號：1945336