β-环糊精与苯并咪唑和萘等衍生物相互作用及山竹黄酮和丹参素类化合物结构的核磁共振研究
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摘要
超分子化学是化学领域的一门交叉学科,被认为是21世纪新概念和高新技术的重要源头之一,是当代化学的前言。β-环糊精作为一类重要的超分子体系,其最显著的结构特征是存在一个立体手性疏水空腔,它的结构特性使其作为分子受体、人工酶模型和药物载体在科学和技术众多领域有着广泛的应用,在分子识别、分子自组装等研究方面对超分子化学有着重要的意义。苯并咪唑及其衍生物是有机合成中重要的原料和中间体,是一种存在于多种药物中的重要结构单元。核磁共振作为研究超分子化学的一种手段,由于其方便快捷,不损坏样品,又可提供大量有用的数据,现已成为研究超分子化学必不可少的实验方法。通过核磁共振的方法研究β-环糊精与苯并咪唑及其衍生物之间的相互识别,可以了解β-环糊精与苯并咪唑及其衍生物的作用形式、作用点、包结物的稳定性及空间构型,为后面的合成、应用起到一个探索新路径的作用。
本文在总结超分子化学及核磁共振的发展及应用的基础上,以邻苯二胺为原料,合成了几种苯并咪唑衍生物,作为分子识别中的客体小分子。通过核磁共振的方法研究了主体分子β-环糊精与7种客体小分子1,3-二甲基-2-环丙基苯并咪唑、2-甲基苯并咪唑、1,2-二乙基苯并咪唑、2-苯基苯并咪唑、1,3-二甲基-2-环已基苯并咪唑、β-萘酚、1-氨基-8-萘酚-3,6-二磺酸钠盐形成的超分子体系,并说明了形成的空间结构。
另外,通过核磁共振的方法,对α-山竹黄酮的结构进行了全归属,通过~1H、~(13)C、COSY、ROESY、HMBC等方法分析了其空间构型;研究了不同取代基对丹参素衍生物质子化学位移的影响。
Supramolecular chemistry is one of the new branches of the chemistry,it has been regarded as one of the important headstream of new conception and advanced technique.Supramolecular chemistry is the foreword of modern chemistry.β-Cyclodextrin is regard as a kind of important supramolecular system,which is the most important host compound,the most useful with respect to the other compounds of recognition and assembly.Benzimidazole and their derivatives are important material and intermediate product,it is a important structure cell which consist in many medicines.NMR is one of the powerful methods use to study the supramolecular chemistry,it is no damage,convenience and offer abundant data,so it was widely used to the supramolecular chemistry.We study the recognition betweenβ-Cyclodextrin and Benzimidazole derivatives by NMR method.We find out their action form and the stability constant of inclusion complex.These investigation find out a new method for synthesization.
The development and application of supramolecular chemistry and NMR were reviewed.Based on that,several benzimidazole derivatives were synthesized from o-phenylenediamine.The spatial structures and supramolecular systems that formed byβ-CD with seven guest compounds,1,3-dimethyl-2-cyclopropyl benzoimidazolium salt,2-methyl benzimidazole,1,2-diethyl benzoimidazolium salt,2-phenyl-benzimi-dazole,1,3-dimethyl-2-cyclohexyl benzoimidazolium salt,β- naphthol,1-amino-8-napthol-3,6-disulfonic acid sodium salt,were studied by NMR.
In addition,the ascription and spatial structure ofα-mangostin and effect of the different substituted groups of tanshinol derivatives were investigated by ~1H,~(13)C, COSY,ROESY,HMBC.
本文在总结超分子化学及核磁共振的发展及应用的基础上,以邻苯二胺为原料,合成了几种苯并咪唑衍生物,作为分子识别中的客体小分子。通过核磁共振的方法研究了主体分子β-环糊精与7种客体小分子1,3-二甲基-2-环丙基苯并咪唑、2-甲基苯并咪唑、1,2-二乙基苯并咪唑、2-苯基苯并咪唑、1,3-二甲基-2-环已基苯并咪唑、β-萘酚、1-氨基-8-萘酚-3,6-二磺酸钠盐形成的超分子体系,并说明了形成的空间结构。
另外,通过核磁共振的方法,对α-山竹黄酮的结构进行了全归属,通过~1H、~(13)C、COSY、ROESY、HMBC等方法分析了其空间构型;研究了不同取代基对丹参素衍生物质子化学位移的影响。
Supramolecular chemistry is one of the new branches of the chemistry,it has been regarded as one of the important headstream of new conception and advanced technique.Supramolecular chemistry is the foreword of modern chemistry.β-Cyclodextrin is regard as a kind of important supramolecular system,which is the most important host compound,the most useful with respect to the other compounds of recognition and assembly.Benzimidazole and their derivatives are important material and intermediate product,it is a important structure cell which consist in many medicines.NMR is one of the powerful methods use to study the supramolecular chemistry,it is no damage,convenience and offer abundant data,so it was widely used to the supramolecular chemistry.We study the recognition betweenβ-Cyclodextrin and Benzimidazole derivatives by NMR method.We find out their action form and the stability constant of inclusion complex.These investigation find out a new method for synthesization.
The development and application of supramolecular chemistry and NMR were reviewed.Based on that,several benzimidazole derivatives were synthesized from o-phenylenediamine.The spatial structures and supramolecular systems that formed byβ-CD with seven guest compounds,1,3-dimethyl-2-cyclopropyl benzoimidazolium salt,2-methyl benzimidazole,1,2-diethyl benzoimidazolium salt,2-phenyl-benzimi-dazole,1,3-dimethyl-2-cyclohexyl benzoimidazolium salt,β- naphthol,1-amino-8-napthol-3,6-disulfonic acid sodium salt,were studied by NMR.
In addition,the ascription and spatial structure ofα-mangostin and effect of the different substituted groups of tanshinol derivatives were investigated by ~1H,~(13)C, COSY,ROESY,HMBC.
引文
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