本文選題：苯并二氫呋喃類木脂素 + 全合成　； 參考：《青島科技大學(xué)》2014年碩士論文

【摘要】：木脂素類化合物是一類由苯丙素單元氧化聚合形成的天然產(chǎn)物，在自然界中分布較為廣泛，具有獨特的藥理活性。由于其具有新穎的化學(xué)結(jié)構(gòu)、多個手性中心、以及豐富的官能團使其成為了化學(xué)家們廣泛關(guān)注的焦點。其中本文關(guān)注的苯并二氫呋喃類木脂素以及8-5’新木脂素也是具有廣泛生理和藥理活性的天然木脂素。本文主要對苯并二氫呋喃類新木脂素Boehmenan H進行了首次全合成研究，并對8-5’新木脂素的合成進行了探索，本文內(nèi)容共包括以下三部分： 第一部分綜述，介紹了木脂素化合物目前研究現(xiàn)狀包括其分類、理化性質(zhì)及其生物活性等等。主要闡述了天然木脂素類化合物的合成研究，并根據(jù)當(dāng)前的研究現(xiàn)狀提出本課題的主要內(nèi)容及研究方向。 第二部分詳細介紹了苯并二氫呋喃類木脂素Boehmenan H的首次全合成研究。以廉價的香草醛為原料，與丙二酸二乙酯經(jīng)過克腦文蓋反應(yīng)生成阿魏酸乙酯，通過氧化銀催化的仿生氧化偶聯(lián)反應(yīng)，形成了苯并二氫呋喃骨架。通過兩次酯基的還原和一次羥基的DHP保護，得到中間產(chǎn)物單醇，最后和甲氧基甲醚保護的阿魏酸衍生物反應(yīng)，得到前目標化合物，然后再經(jīng)過脫除保護基得到具有藥理活性的目標化合物Boehmenan H。 第三部分主要介紹了苯并二氫呋喃環(huán)在不同的堿性條件下的開環(huán)反應(yīng)，并深入探討了它們的開環(huán)反應(yīng)機理。這些開環(huán)反應(yīng)證明了苯并二氫呋喃環(huán)在堿性條件下很不穩(wěn)定，，極易開環(huán)，為8-5’新木脂素類化合物合成提供了新的方法和途徑。
[Abstract]:Lignans are a kind of natural products formed by unit oxidation polymerization of phenylpropanin, which are widely distributed in nature and have unique pharmacological activities. Because of its novel chemical structure, many chiral centers and abundant functional groups, it has become the focus of chemists. The benzodihydrofuran lignans and 8-5 '-neophorin are also natural lignans with a wide range of physiological and pharmacological activities. In this paper, the first total synthesis of benzodihydrofuran new lignans (Boehmenan H) was studied, and the synthesis of 8-5 'new lignans was explored. In the first part, the present research status of lignans including their classification, physicochemical properties and biological activities were reviewed. In this paper, the synthesis of natural lignans is reviewed, and the main contents and research directions of this subject are put forward according to the current research situation. In the second part, the first total synthesis of benzodihydrofuran lignans (Boehmenan H) was introduced in detail. Using cheap vanillin as raw material, diethyl malonate was reacted with diethyl malonate to form ethyl ferulic acid, and the benzodihydrofuran skeleton was formed by the bionic oxidative coupling reaction catalyzed by silver oxide. Through the reduction of two ester groups and the DHP protection of the first hydroxyl group, the intermediate monoalcohol was obtained. Finally, the intermediate product was reacted with the ferulic acid derivative protected by methoxy methyl ether, and the former target compound was obtained. After removing the protective group, the target compound with pharmacological activity, Boehmenan H. In the third part, the ring opening reaction of benzodihydrofuran ring under different basic conditions was introduced, and the mechanism of ring opening reaction was discussed. These ring-opening reactions have proved that the benzodihydrofuran ring is unstable and easy to open in alkaline conditions, which provides a new method and approach for the synthesis of 8-5 '-lignans.
【學(xué)位授予單位】：青島科技大學(xué)
【學(xué)位級別】：碩士
【學(xué)位授予年份】：2014
【分類號】：R914

【參考文獻】

相關(guān)期刊論文 前10條

1 劉國強,高錦明,吳文君;植物源殺蟲成分研究新進展[J];西北植物學(xué)報;2002年03期

2 蔣達榮;關(guān)于氫化鋁鋰和硼氫化鈉還原醛酮成醇的反應(yīng)式[J];大學(xué)化學(xué);1997年04期

3 ;A new lignan derivative from the root of Ilex pubescens[J];Chinese Chemical Letters;2008年05期

4 ;Synthesis and Antitumor Activity of New Derivatives of Podophyllotoxin[J];Chinese Chemical Letters;1996年11期

5 王莉莉;周應(yīng)軍;;抗癌物質(zhì)鬼臼毒素及其衍生物研究進展[J];國外醫(yī)藥(植物藥分冊);2006年01期

6 程麗姣;丁羽佳;翟永功;趙長琦;;119植物中新的木脂素類化合物及其生物活性[J];國外醫(yī)藥(植物藥分冊);2006年03期

7 ;SYNTHESIS OF DIISOFERULIC ACID[J];Chinese Chemical Letters;1994年06期

8 張永忠,李小莉,郭群;辛夷木脂素類成分抗血小板活化因子(PAF)作用的研究[J];湖北中醫(yī)雜志;2001年10期

9 汪秋安,麻秋娟,黎艷玲;仿生氧化偶聯(lián)合成苯并二氫呋喃新木脂素Balanophonin[J];湖南大學(xué)學(xué)報(自然科學(xué)版);2003年04期

10 周漢芬;李建芬;;有機堿催化Knoevenagal法合成肉桂酸及其工藝優(yōu)化[J];化學(xué)工程師;2007年07期

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