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学科主题: 药物化学
题名:
基于吲哚和其他芳烃的氧化脱氢偶联研究
作者: 吴国菻
答辩日期: 2013-12-30
导师: 焦宁
专业: 药物化学
授予单位: 北京大学
授予地点: 北京大学药学院
学位: 硕士
关键词: 吲哚、烯酮、串联、烯基化、烯基导向、碳氢键活化、萘环
其他题名: Study on Dehydrogenative Coupling Based on Indole and Other Aromatic Molecules
分类号: R914.4
摘要: 吲哚在天然产物和活性分子中广泛存在。含有吲哚结构的甾体和多肽类化合物具有各种各样的生物活性。烯基吲哚化合物在生物活性分子中具有重要意义。合成烯基吲哚的方法绝大部分是采用过渡金属催化的吲哚的烯基化偶联反应,但是过渡金属催化的反应一般难以控制反应的选择性,过渡金属的残留会导致产物需要进一步纯化同时反应底物结构有局限性。论文阐述了在有机催化剂作用下吲哚与烯酮Michael加成并串联氧化反应,选择性在吲哚-3-位引入烯基的方法。该方法使用价廉易得的有机催化剂催化反应,同时利用串联反应避免了分离反应中间体,降低了反应成本。反应适用于多种取代吲哚。萘环骨架在天然产物中具有重要意义,多种天然产物和活性分子结构中含有萘环骨架。论文第二部分我们发现了烯基导向下碳氢键活化插入炔烃,最终生成萘环的反应,是一种全新的构建萘环骨架的方法。反应在以醋酸钯作为催化剂,苯醌作为氧化剂,醋酸为溶剂条件下,烯丙基苯与炔烃反应生成萘环。反应体系简单,原料简单易得。但是产率不能令人满意,反应仍需继续探索。
英文摘要: Indole moiety exists extensively in bioactive molecules and natural products. Steroids bearing indole structure and polypeptide compound manifest a variety of biological activities. Indole compounds bearing alkenyl group outstand for their potential bioactivities. Most methods to synthesize vinyl indole are vinylation of indole catalyzed by transition metal. However, it is difficult to control the selectivity of reaction catalyzed by transition metal. The transition metal residue also needs further purification and the substrate scope is usually limited. In this paper, we developed a tandem reaction of Michael addition and oxidation of indole and α,β-unsaturated ketone, catalyzed by organic molecules, selectively generating 3-vinylindole. The utilization of inexpensive, readily available organic catalyst and tandem reaction methods contribute to avoidance of separating reaction intermediates and reducing expense. The reaction apply to a variety of substituted indoles. Naphthalene signifies in natural products. various active molecules contain a naphthalene. In the second part of the manuscript, we developed alkene directed C-H bond activation, inserting alkyne, generating the final product naphthalene structure. It is a new method to construct naphthalene skeleton. The reaction employs palladium acetate, benzoquinone, acetic acid as catalyst, oxidant, solvent separately, transforming allyl benzene and alkynes into naphthalene. The reaction condition is simple, the substrate is easy to obtain. However, the yield is not satisfactory, the reaction still needs further exploration.
语种: 中文
出处: http://xuewei.bjmu.edu.cn/simpsearch.action?keyword=基于吲哚和其他芳烃的氧化脱氢偶联研究&dbid=72
相关网址: 查看原文
内容类型: 学位论文
URI标识: http://ir.bjmu.edu.cn/handle/400002259/107274
Appears in Collections:北京大学药学院_学位论文

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作者单位: 北京大学药学院

Recommended Citation:
吴国菻. 基于吲哚和其他芳烃的氧化脱氢偶联研究[D]. 北京大学药学院. 北京大学. 2013.
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