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  本文選題：半縮醛 + 多取代四氫呋喃環(huán)�。� 參考：《蘇州大學(xué)》2014年碩士論文

【摘要】：含氧脂肪雜環(huán)是一類廣泛存在于各種天然產(chǎn)物和已上市藥物中的化學(xué)結(jié)構(gòu)，其在生物、醫(yī)藥、農(nóng)藥等領(lǐng)域都具有重要的應(yīng)用價值。特別值得一提的是，DNA結(jié)構(gòu)中的脫氧核糖核酸單元的四氫呋喃核心也是一種含氧脂肪雜環(huán)，這樣的結(jié)構(gòu)也存在于核苷類藥物中，廣泛應(yīng)用于抗腫瘤和抗病毒等。 有機(jī)催化的不對稱Michael加成反應(yīng)是一類構(gòu)建C-C鍵、C-N鍵、C-O鍵等的重要方法，具有對環(huán)境污染小、穩(wěn)定性好、價格便宜、綠色環(huán)保且可一步合成多個手性中心等優(yōu)點(diǎn)。本論文報(bào)道的是利用2-羥基四氫呋喃這樣一種半縮醛結(jié)構(gòu)化合物在有機(jī)催化劑的作用下與各種親電底物反應(yīng)得到一系列的四氫呋喃多取代衍生物，這樣可以制得高對映異構(gòu)體純度的化合物。同樣對天然產(chǎn)物的全合成及藥物的發(fā)現(xiàn)也具有重要意義。 本論文第一部分對含有四氫呋喃環(huán)的天然產(chǎn)物及化學(xué)藥物進(jìn)行了綜述，并對合成四氫呋喃環(huán)結(jié)構(gòu)的研究方法進(jìn)行了簡要概述，并介紹了催化劑二苯基脯氨醇三甲基硅醚催化的不對稱Michael加成反應(yīng)的研究進(jìn)展。 本論文第二部分對2-羥基四氫呋喃和硝基烯的高效不對稱Michael加成反應(yīng)進(jìn)行了詳細(xì)研究，得到的手性3-取代半縮醛產(chǎn)物進(jìn)一步進(jìn)行結(jié)構(gòu)修飾得到了一系列文拉法辛類似物，測試其抗抑郁活性發(fā)現(xiàn)，其中三個化合物的活性接近于文拉法辛。 本論文第三部分對2-羥基四氫呋喃與其他親電底物的不對稱反應(yīng)進(jìn)行了廣泛的初步研究，這些親電底物包括鄰羥基硝基苯乙烯、醌、馬來酰亞胺等，證明了半縮醛在各類親電底物中的廣泛應(yīng)用性。
[Abstract]:Oxygenated aliphatic heterocycles are a class of chemical structures which are widely used in various natural products and listed drugs. They have important application value in biology, medicine, pesticide and so on. It is especially worth mentioning that the tetrahydrofuran core of DNA unit in DNA structure is also an oxygen-containing fatty heterocycle which is also present in nucleoside drugs and is widely used in anti-tumor and anti-virus. Organic catalyzed asymmetric Michael addition reaction is an important method to construct C-C bond C-N bond and C-O bond. It has the advantages of low environmental pollution, good stability, low price, green environment and the ability to synthesize many chiral centers in one step. In this paper, a series of tetrahydrofuran polysubstituted derivatives were synthesized by the reaction of 2-hydroxytetrahydrofuran with various electrophilic substrates under the action of organic catalyst. In this way, a compound with high enantiomer purity can be prepared. It is also of great significance to the synthesis of natural products and the discovery of drugs. In the first part of this thesis, the natural products and chemical drugs containing tetrahydrofuran ring are reviewed, and the research methods for the synthesis of tetrahydrofuran ring structure are briefly summarized. The research progress of asymmetric Michael addition catalyzed by diphenyl proline trimethylsilyl ether was also introduced. In the second part of this thesis, the highly efficient asymmetric Michael addition reaction between 2-hydroxytetrahydrofuran and nitroene was studied in detail. The chiral 3-substituted semi-acetals were further modified to obtain a series of venlafaxine analogues. The antidepressant activity of three of the compounds was similar to that of venlafaxine. In the third part of this thesis, the asymmetric reactions of 2-hydroxytetrahydrofuran with other electrophilic substrates, such as o-hydroxynitrobenzene, quinone, maleimide, were studied. It is proved that hemiacetal is widely used in various electrophilic substrates.
【學(xué)位授予單位】：蘇州大學(xué)
【學(xué)位級別】：碩士
【學(xué)位授予年份】：2014
【分類號】：R914.5

【參考文獻(xiàn)】

相關(guān)期刊論文 前1條

1 陳勇;李祥;陳建偉;徐莎莎;王玉;邱海龍;;雙四氫呋喃型番荔枝內(nèi)酯體內(nèi)抗腫瘤作用[J];中草藥;2012年01期

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本文編號：2118037