新型三嗪环蕃及吡啶环蕃的合成研究
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摘要
超分子化学是化学领域的一门交叉学科,与材料科学、信息科学、生命科学等学科紧密相关,处于当代化学前沿。具有新的形状和几何构型的人工大环化合物的设计、合成与应用是有机化学和超分子化学的研究热点之一,在分子识别基础上形成主-客体配合物是超分子体系的基本特征,冠醚、环糊精、杯芳烃、环蕃作为主客体化学最具有代表性的主体化合物在基础研究和许多领域都取得了令人瞩目的成果。
环蕃作为一种重要的大环化合物,它的性质被化学家进行了广泛的研究。从结构看它是将芳香环由亚甲基桥连起来的环状化合物,分子内具有空腔,该空腔上的芳环是侧立的,具有一定的深度,并且具有疏水的性质。作为人工模拟酶,利用疏水性空腔,根据环的形状、大小以及静电作用等的不同,可以俘获不同种类的有机分子,形成主-客体包结物。目前环蕃研究领域的一个方向是对环蕃的骨架结构实施改变,包括用某些杂环化合物例如吡啶、咪唑、苯并咪唑、三嗪、噻吩等代替苯环而形成的杂环环蕃,或用杂原子S、N、O或含杂原子的基团代替桥联亚甲基而形成的杂原子桥连环蕃,杂原子的引入改变了环蕃的主体结构和键合性能,以适合不同的底物分子。
论文对三嗪环蕃和吡啶环蕃的合成进行了研究,在第一部分对超分子化学以及环蕃化学进行了介绍,列举了各类杂环环蕃—吡啶环蕃、咪唑环蕃、吲哚环蕃、四硫富瓦烯环蕃、三嗪环蕃、苯并三唑环蕃等的研究现状,并且介绍了环蕃的发展情况以及研究前景;第二部分报道了几种杂原子三嗪环蕃的合成方法以及表征数据,利用“片段偶联合成法”,以简单易得的价廉原料、在温和的条件下高效和高产率地合成了几种杂原子桥连的三嗪环蕃化合物;第三部分报道了一种含吡啶环的环蕃的合成方法,以间二甲苯为原料合成了间二苯甲酸,间二苯甲酰氯,再与乙酰乙酸乙酯钠盐反应合成间苯二甲酰二乙酰基乙酸乙酯,间苯二甲酰二乙酸乙酯,最后通过汉栖(Hantzsch)合成法合成了两种新的吡啶环蕃。
Supramolecular chemistry is a cross subject in chemistry, which is contact with material sciences and information sciences, life sciences. It is at the forefront of contemporary chemistry. In organic chemistry and supramolecular chemistry, the design, synthesis and application of artificial macrocyclic compound with novel shapes and geometries have been continued to be of interest. The basic feature of supramolecular chemistry comes into being the host-guest complex in the basis of molecular recognition. As the most representative objects of host compounds, crown ethers, cyclodextrins, calixarenes, cyclophanes have achieved remarkable results in the main body of basic research and many areas.
As a sort of important macrocyclic compound, the properties of cyclophane have been researched by chemists extensively. It is a kind of circular compound connected by methylene bridged and aromatic ring. There is a hole in the molecule and in which the aromatic ring is placed sideway, so the molecule is hydrophobic. As an artificially simulated enzyme, cyclophane can capture different organic molecules to form host-guest inclusive complex according to the differences of the ring shape, size and electrostatic effect. Currently, one direction of cyclophane research areas is changing the ring skeleton of the cyclophane structure, including the use of certain heterocyclic compounds such as pyridine, imidazole, benzimidazole, triazine, thiophene instead of benzene ring and with hetero-atoms S, N, O instead of methylene-bridged to form heterocyclophanes. The introduction of heteroatom changed the structure and the bonding performance of the cyclophane, which can fit different substrate molecules.
This thesis did research on the synthesis of triazine-based cyclophane and pyridinophane. In part 1, a brief introduction of supramolecular chemistry and cyclophane chemistry, the development of pyridinophane, midazolophane, indolophane, tetrathiafulvalene cyclophane, benzotriazolophane and triazine-based cyclophane have been provided as well as a presentation of actuality and the foreground of the cyclophane research; In part 2, synthetic methods and the characterizations of several novel triazine-based cyclophanes were presented. By a fragment coupling approach, a number of hetero atoms -bridged triazine-based cyclophanes have been synthesized through cheap raw materials, an unusually high yielding and efficiency in gentle condition; In part 3, the synthetic method of pyridinophane was reported, the isophthalic acid and isophthalyl chloride were synthesized taking m-xylene as the raw material. With isophthalyl chloride and the Na salt of acetoacetate ester, the isophthaloyl-di-acetic ester was synthesized, finally two novel pyridinophane were obtained by Hantzsch synthetic method.
环蕃作为一种重要的大环化合物,它的性质被化学家进行了广泛的研究。从结构看它是将芳香环由亚甲基桥连起来的环状化合物,分子内具有空腔,该空腔上的芳环是侧立的,具有一定的深度,并且具有疏水的性质。作为人工模拟酶,利用疏水性空腔,根据环的形状、大小以及静电作用等的不同,可以俘获不同种类的有机分子,形成主-客体包结物。目前环蕃研究领域的一个方向是对环蕃的骨架结构实施改变,包括用某些杂环化合物例如吡啶、咪唑、苯并咪唑、三嗪、噻吩等代替苯环而形成的杂环环蕃,或用杂原子S、N、O或含杂原子的基团代替桥联亚甲基而形成的杂原子桥连环蕃,杂原子的引入改变了环蕃的主体结构和键合性能,以适合不同的底物分子。
论文对三嗪环蕃和吡啶环蕃的合成进行了研究,在第一部分对超分子化学以及环蕃化学进行了介绍,列举了各类杂环环蕃—吡啶环蕃、咪唑环蕃、吲哚环蕃、四硫富瓦烯环蕃、三嗪环蕃、苯并三唑环蕃等的研究现状,并且介绍了环蕃的发展情况以及研究前景;第二部分报道了几种杂原子三嗪环蕃的合成方法以及表征数据,利用“片段偶联合成法”,以简单易得的价廉原料、在温和的条件下高效和高产率地合成了几种杂原子桥连的三嗪环蕃化合物;第三部分报道了一种含吡啶环的环蕃的合成方法,以间二甲苯为原料合成了间二苯甲酸,间二苯甲酰氯,再与乙酰乙酸乙酯钠盐反应合成间苯二甲酰二乙酰基乙酸乙酯,间苯二甲酰二乙酸乙酯,最后通过汉栖(Hantzsch)合成法合成了两种新的吡啶环蕃。
Supramolecular chemistry is a cross subject in chemistry, which is contact with material sciences and information sciences, life sciences. It is at the forefront of contemporary chemistry. In organic chemistry and supramolecular chemistry, the design, synthesis and application of artificial macrocyclic compound with novel shapes and geometries have been continued to be of interest. The basic feature of supramolecular chemistry comes into being the host-guest complex in the basis of molecular recognition. As the most representative objects of host compounds, crown ethers, cyclodextrins, calixarenes, cyclophanes have achieved remarkable results in the main body of basic research and many areas.
As a sort of important macrocyclic compound, the properties of cyclophane have been researched by chemists extensively. It is a kind of circular compound connected by methylene bridged and aromatic ring. There is a hole in the molecule and in which the aromatic ring is placed sideway, so the molecule is hydrophobic. As an artificially simulated enzyme, cyclophane can capture different organic molecules to form host-guest inclusive complex according to the differences of the ring shape, size and electrostatic effect. Currently, one direction of cyclophane research areas is changing the ring skeleton of the cyclophane structure, including the use of certain heterocyclic compounds such as pyridine, imidazole, benzimidazole, triazine, thiophene instead of benzene ring and with hetero-atoms S, N, O instead of methylene-bridged to form heterocyclophanes. The introduction of heteroatom changed the structure and the bonding performance of the cyclophane, which can fit different substrate molecules.
This thesis did research on the synthesis of triazine-based cyclophane and pyridinophane. In part 1, a brief introduction of supramolecular chemistry and cyclophane chemistry, the development of pyridinophane, midazolophane, indolophane, tetrathiafulvalene cyclophane, benzotriazolophane and triazine-based cyclophane have been provided as well as a presentation of actuality and the foreground of the cyclophane research; In part 2, synthetic methods and the characterizations of several novel triazine-based cyclophanes were presented. By a fragment coupling approach, a number of hetero atoms -bridged triazine-based cyclophanes have been synthesized through cheap raw materials, an unusually high yielding and efficiency in gentle condition; In part 3, the synthetic method of pyridinophane was reported, the isophthalic acid and isophthalyl chloride were synthesized taking m-xylene as the raw material. With isophthalyl chloride and the Na salt of acetoacetate ester, the isophthaloyl-di-acetic ester was synthesized, finally two novel pyridinophane were obtained by Hantzsch synthetic method.
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