叔膦参与的环化反应研究

发布时间：2018-03-21 01:37

  本文选题：叔膦　切入点：靛红衍生物　出处：《扬州大学》2017年硕士论文　论文类型：学位论文

【摘要】：叔膦作为一类重要的有机膦化合物,在有机合成中有重要的用途。叔膦具有较强的夺氧能力,在很多经典的有机人名反应如Wittig反应、Mitsunobu反应以及Staudinger反应中,膦的夺氧能力对完成相关的化学转化起到了关键的作用。叔膦具有较强的亲核性,源于磷原子给出孤对电子的能力和可极化性。近年来,叔膦作为亲核有机催化剂作用下的有机新反应大量涌现,为其在有机合成中的应用开辟了新的领域。由于叔膦这些特殊的化学性质决定了它在有机合成中具有广泛的用途,研究叔膦促进下的有机合成方法学已经成为当今有机化学领域中的一个重要研究方向,吸引了有机化学家的浓厚兴趣。本论文进行了一系列叔膦参与的环化反应研究。1.研究了三苯基膦、丁炔二酸二酯和苄叉茚满二酮参与的三组分反应,形成了 14个螺[环戊[2]烯-1,2'-二氢茚]衍生物。而三苯基膦、丁炔二酸二酯和苄叉氰基频那酮的三组分反应则形成了 12个密取代二氢呋喃衍生物。所合成的26个化合物都通过了核磁、红外、高分辨质谱等手段的表征,并用单晶衍射方法测定了其中4个化合物的单晶结构。2.研究了P NMe2)3、取代靛红与苄叉氰基频那酮等参与的环化反应,形成了一系列密取代的环丙烷衍生物。所合成的27个化合物都通过了核磁、红外、高分辨质谱等手段的表征,并用单晶衍射方法测定了其中2个化合物的单晶结构。3.研究了四个药物中间体的合成工艺。合成路线合成步骤少,所使用的原料价格低廉,并且具有较高的收率,纯化过程较为简单。产品则通过了核磁,气相,液相等手段的表征。
[Abstract]:Tert-phosphine, as an important organic phosphine compound, has important applications in organic synthesis. Tert-phosphine has a strong ability to capture oxygen, in many classical organic name reactions such as Wittig reaction, Mitsunobu reaction and Staudinger reaction. The ability of phosphine to capture oxygen plays a key role in the completion of chemical transformation. Tert-phosphine has strong nucleophilic properties due to the ability and polarizability of phosphorus atoms to give lone pairs of electrons. Tert-phosphine, as a nucleophilic organic catalyst, has sprung up in large numbers, which opens up a new field for its application in organic synthesis. Because of its special chemical properties, tert-phosphine has a wide range of applications in organic synthesis. The research on the methodology of organic synthesis promoted by tert-phosphine has become an important research direction in the field of organic chemistry. In this paper, a series of cyclization reactions involving tert-phosphine were carried out. Fourteen spiroid [cyclopentene [2] ene-2indene-dihydroindene] derivatives were formed, and triphenylphosphine, In the three-component reaction of diester butyronate and benzyl cyanoquinone, 12 intermediate-substituted dihydrofuran derivatives were formed. All the 26 compounds synthesized were characterized by NMR, IR and high resolution mass spectrometry. The single crystal structure of four compounds was determined by single crystal diffraction. The cyclization reaction of substituted indirubin with benzyl dithiocyanone was studied. A series of densely substituted cyclopropane derivatives were formed. The 27 compounds synthesized were characterized by nuclear magnetic field, infrared spectroscopy, high resolution mass spectrometry, etc. The single crystal structure of two of the compounds was determined by single crystal diffraction method. The synthetic process of four pharmaceutical intermediates was studied. The purification process was relatively simple. The product was characterized by nuclear magnetic field, gas phase and liquid phase.
【学位授予单位】：扬州大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O621.25
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本文编号：1641681