N-取代吲哚衍生物的合成及波谱解析

Synthesis and Spectrum Analysis of N-Ssubstituted Indole Derivatives

作者: 专业:有机化学 导师:叶勇 年度:2010 学位:硕士  院校: 郑州大学

Keywords

Indole, N-substituted Indole Derivatives, Synthesis, Spectrum Analysis

        吲哚衍生物是一类非常重要的有机原料和化工产品。含有吲哚环的化合物广泛存在于自然界,在已知的天然产物中占有相当大的比例。由于其独特的化学结构,大多数吲哚环类化合物都显示出重要的生物或化学性质,在农业、工业及医药等领域有着十分重要的用途。随着人们对吲哚化合物用途认识的不断深入,关于吲哚类化合物合成方法的研究报道也越来越多,本文结合相关文献报道对此也作了简单的概述。本论文主要通过吲哚环N原子上的亲核取代反应设计合成了一系列N-取代的吲哚衍生物。通过一维和二维核磁共振技术对不同N-取代的吲哚化合物的1HNMR和13C NMR做了全归属,比较了相关谱图之间的关系,探讨了其中的规律,对其原因也作了相关的分析。例如,N-取代的3-甲基吲哚衍生物和5-苄氧基吲哚衍生物吲哚上相关质子和碳的化学位移都比相应的吲哚上没有取代基的N-取代的吲哚衍生物上质子质子和碳的化学位移向高场移动,这可能是由于取代基给电子作用的影响。利用电喷雾质谱对目标分子电喷雾多级质谱的分析,归纳出了此类化合物的裂解规律。由于吲哚环自身的相对稳定性,裂解过程中目标化合物的C-N或S-N键是易断裂的位点,根据化合物多级质谱数据判断失去哪些官能团,佐证了化合物的分子结构。这些结果对以后判别此类化合物提供了参考。最后对所有化合物做了红外吸收光谱的对比研究。
    Indole derivatives is a very important class of organic raw materials and chemical products. The compounds containing indole ring are widespread in nature, which occupy a large proportion of the known natural products. Usually, most of these compounds have significant property due to its particular chemical structure, and have an important role in agriculture, industry, medicine, etc. Based on the understanding about the application of indole derivatives, many synthetic methodologies of indole derivatives have been reported.In this dissertation, we also gave a brief summary about it.In this dissertation, series of N-substituted indole derivatives were designed and synthesized mainly based on the nucleophilic substitution reaction of indole ring. Through 1D and 2D NMR techniques,1H and 13C NMR signals of different N-substituted indole derivatives were assigned.The relevant spectrums were compared and some conclutions were drawn from it. For example, the chemical shifts of protons and carbons in the indole ring of N-substituted 3-methyl indole derivatives and 5-benzyloxy indole derivatives are higher than the corresponding N-substituted Indole ring derivatives not substituted, which may be due to the electronic substituent effects. The fragmentation pathway of mass spectra of these compounds were studied and summarized according to Electrospray Ionization Mass Spectrometry(ESI-MS).We find that the C-N and S-N bonds are easy to break in the mass spectrometric, which may be due to the relative stability of the indole ring itself. The molecular structure can be identified from fragment ion of compounds in electrospray ionization mass spectrometer. All the conclutions can be used as references to other analogues. Finally, all the compounds were studied by the infrared absorption spectrum.
        

N-取代吲哚衍生物的合成及波谱解析

摘要4-5
Abstract5
目录6-8
第一章 前言8-25
    1.1 吲哚衍生物及其应用8-12
    1.2 吲哚衍生物的合成方法12-19
        1.2.1 Fischer吲哚合成法12-14
        1.2.2 Larock杂环化合成法14-15
        1.2.3 亲核环化合成法15-16
        1.2.4 还原环化合成法16-18
        1.2.5 其它合成方法18-19
    1.3 波谱分析技术的应用及发展19-24
        1.3.1 核磁共振波谱19-22
        1.3.2 质谱技术22-24
    1.4 本硕士论文的研究背景及研究内容24-25
第二章 N-取代吲哚衍生物的合成研究25-40
    2.1 引言25-26
    2.2 试剂和仪器26-27
        2.2.1 试剂26
        2.2.2 仪器26-27
    2.3 合成部分27-38
        2.3.1 N-对甲苯磺基吲哚衍生物的合成27-29
        2.3.2 N-苄基吲哚衍生物的合成29-32
        2.3.3 N-甲基吲哚衍生物的合成32-34
        2.3.4 N-苯基吲哚衍生物的合成34-36
        2.3.5 N-Boc吲哚衍生物的合成36-38
    2.4 结果与讨论38-40
第三章 化合物核磁与质谱裂解途径分析40-58
    3.1 化合物核磁表征规律40-54
        3.1.1 化合物N-对甲苯磺基吲哚(a)的结构解析40-45
        3.1.2 化合物N-对甲苯磺基-3-甲基吲哚(b)的结构解析45-49
        3.1.3 化合物N-甲基吲哚(g)的结构解析49-52
        3.1.4 目标化合物的核磁规律分析52-54
    3.2 化合物质谱和红外表征54-58
第四章 结论58-59
附图59-70
参考文献70-74
硕士期间发表的论文74-75
致谢75
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