三维结构的光学活性笼状环芳分子的设计与合成
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摘要
以碳-碳三键为桥联的环芳化学,特别是富碳化合物和构型保持的大环类化合物研究,是现代环芳化学研究中最引人注目的领域之一。
环芳化合物的性质取决于它的几何形状、电子效应和芳环上的取代基。三键的刚性结构可以使大环骨架得以很好的扩展,而苯环可以控制三键桥联的方向,从某种意义上决定了整个分子的形状。三键和芳香环的组合可以形成一系列形态各异的平面或三维环芳化合物。通过C≡C的连接,各种芳香环可以组合成形状特定的二维或三维的大环化合物。它们在分子构型、分子手性、液晶材料和传感材料等方面的潜在应用被广泛研究。其中一些高度不饱和的此类化合物被作为是有序碳材料的前驱体。本文在本实验室以前的工作的基础上设计并合成了一系列新型的光学活性的环芳化合物及其衍生物。
由于联萘在反应前后构型保持稳定,以及乙炔键在空间上良好的定向作用,本文选择了光学活性的2,2'-二乙炔基.1,1'-联萘作为合成模板来构筑目标分子。本文第二章主要讨论具有单一手性[(R)构型或(S)构型]的2,2'-二乙炔基-1,1'-联萘模板的合成。以光学纯的(R)-或(S)-联萘二酚为起始原料,通过酚羟基的酯化反应、磺酸酯与格氏试剂的Kumada反应、甲基的溴化反应、二溴甲基的水解反应和特殊的Wittig反应来制得2,2'-二乙炔基-1,1'-联萘。
本文第三章从光学纯的(R)-2,2'-二乙炔基-1,1'-联萘为手性模板,设计了分子间和分子内偶联两条反应路线来合成设计的双层三桥联分子。虽未得到设计的目标分子,却都得到了一个双层笼状化合物,并探讨了合成中涉及的几种反应类型:Sonogashira偶联反应,脱去保护基TMS的反应,封管反应,铜盐促进的炔烃偶合反应。
本文第四章解决了第三章中位阻太大,不能形成三桥联分子的问题。通过CPK模型的分子模拟和Chem3D的模拟计算,设计了一个延长的三叉苯炔化合物91作为平面连接桥,并成功地合成了该连接桥。在引入光学纯的(R)-2,2'-二乙炔基-1,1'-联萘为手性模板后,铜盐催化的末端炔偶联成功地合成了设计的双层状的三桥联分子。
本文当中所有的中间体和目标化合物都经过MS、IR、~1H NMR、~(13)C NMR和DEPT组合测定得到确认。
The chemistry of cyclophynes having carbon-carbon triple bond bridges has been one of the most actively investigated fields in modern cyclophane chemistry, particularly in connection with the evolving fields of carbon-rich materials and shapepersistent macrocyclic compounds.
The properties of cyclophynes are characterized by the geometric and electronic properties of triple bonds and the substitution pattern of the aromatic rings.With regard to the geometrical properties,the macrocyclic frameworks of cyclophynes can be expanded by incorporation of triple bonds because of their linearity.The substitution pattern of the aromatic rings,on the other hand,fixes the direction of the bridging triple bonds,defining the whole molecular shape.As a result,a variety of two-and three-dimensional architectures can be built by connecting aromatic rings with triple bond linkages.On the other hand,nonplanar macrocycles of this type have been studied with regard to their conformation,chirality,and their potential application to liquid crystalline and sensing materials.Some highly unsaturated members of this type of compound have been shown to serve as precursors of ordered carbon materials.On the base of our labe was described,and a series of new type of cyclophynes and their derivatives were designed and synthesized.
Because of the stability of binaphthalene's configuration in the reactions and the fine directional function of ethynyl in the space,enantiopure 2,2'-diethynyl-1,1'-binaphthyl was used as synthetic template for the synthesis of target molecules.In the second chapter in this paper,the synthesis of enantiopure[(R)-or(S)-form] 2,2'-diethynyl-1,1'-binaphthyl was described.2,2'-Diethynyl-1,1'-binaphthyl was synthesized from binapythol by esterification of hydroxyl,Kumada reaction of sulfonic ester with Grignard reagent,bromination of methyl,hydrolyzation of dibromomethyl and especial Wittig reaction.
In the third chapter,three-dimensional cage-like cyclophanes 76 were designed and synthesized from enantiopure[(R)-or(S)-form]2,2'-diethynyl(dihydroxy)-1, 1'-binaphthyl,However we have not been given to benzene for the plane of target compounds and got a strange three-dimensional,cage-like cyclophanes.And in the process of synthetic routes involved reaction of several types:Sonogashira reaction, Sealed-tube reaction and Eglinton coupling reaction.
In the forth chapter,we solved the problem of steric hindrance in the third chapter. Through the CPK model of the Chem3D molecular modeling and simulation,we design a three-dimensional compound 91 with an extension trigeminal benzene-acetylene as a flat connecting bridge,three-dimensional cage-like cyclophanes 94 were designed and synthesized though Eglinton coupling reaction from enantiopure[(R)-or(S)-form]2,2'-diethynyl(dihydroxy)-1,1'-binaphthyl.
All the intermediates and target compounds synthesized in this paper were characterized by MS,IR,~1H NMR,~(13)C NMR and DEPT
环芳化合物的性质取决于它的几何形状、电子效应和芳环上的取代基。三键的刚性结构可以使大环骨架得以很好的扩展,而苯环可以控制三键桥联的方向,从某种意义上决定了整个分子的形状。三键和芳香环的组合可以形成一系列形态各异的平面或三维环芳化合物。通过C≡C的连接,各种芳香环可以组合成形状特定的二维或三维的大环化合物。它们在分子构型、分子手性、液晶材料和传感材料等方面的潜在应用被广泛研究。其中一些高度不饱和的此类化合物被作为是有序碳材料的前驱体。本文在本实验室以前的工作的基础上设计并合成了一系列新型的光学活性的环芳化合物及其衍生物。
由于联萘在反应前后构型保持稳定,以及乙炔键在空间上良好的定向作用,本文选择了光学活性的2,2'-二乙炔基.1,1'-联萘作为合成模板来构筑目标分子。本文第二章主要讨论具有单一手性[(R)构型或(S)构型]的2,2'-二乙炔基-1,1'-联萘模板的合成。以光学纯的(R)-或(S)-联萘二酚为起始原料,通过酚羟基的酯化反应、磺酸酯与格氏试剂的Kumada反应、甲基的溴化反应、二溴甲基的水解反应和特殊的Wittig反应来制得2,2'-二乙炔基-1,1'-联萘。
本文第三章从光学纯的(R)-2,2'-二乙炔基-1,1'-联萘为手性模板,设计了分子间和分子内偶联两条反应路线来合成设计的双层三桥联分子。虽未得到设计的目标分子,却都得到了一个双层笼状化合物,并探讨了合成中涉及的几种反应类型:Sonogashira偶联反应,脱去保护基TMS的反应,封管反应,铜盐促进的炔烃偶合反应。
本文第四章解决了第三章中位阻太大,不能形成三桥联分子的问题。通过CPK模型的分子模拟和Chem3D的模拟计算,设计了一个延长的三叉苯炔化合物91作为平面连接桥,并成功地合成了该连接桥。在引入光学纯的(R)-2,2'-二乙炔基-1,1'-联萘为手性模板后,铜盐催化的末端炔偶联成功地合成了设计的双层状的三桥联分子。
本文当中所有的中间体和目标化合物都经过MS、IR、~1H NMR、~(13)C NMR和DEPT组合测定得到确认。
The chemistry of cyclophynes having carbon-carbon triple bond bridges has been one of the most actively investigated fields in modern cyclophane chemistry, particularly in connection with the evolving fields of carbon-rich materials and shapepersistent macrocyclic compounds.
The properties of cyclophynes are characterized by the geometric and electronic properties of triple bonds and the substitution pattern of the aromatic rings.With regard to the geometrical properties,the macrocyclic frameworks of cyclophynes can be expanded by incorporation of triple bonds because of their linearity.The substitution pattern of the aromatic rings,on the other hand,fixes the direction of the bridging triple bonds,defining the whole molecular shape.As a result,a variety of two-and three-dimensional architectures can be built by connecting aromatic rings with triple bond linkages.On the other hand,nonplanar macrocycles of this type have been studied with regard to their conformation,chirality,and their potential application to liquid crystalline and sensing materials.Some highly unsaturated members of this type of compound have been shown to serve as precursors of ordered carbon materials.On the base of our labe was described,and a series of new type of cyclophynes and their derivatives were designed and synthesized.
Because of the stability of binaphthalene's configuration in the reactions and the fine directional function of ethynyl in the space,enantiopure 2,2'-diethynyl-1,1'-binaphthyl was used as synthetic template for the synthesis of target molecules.In the second chapter in this paper,the synthesis of enantiopure[(R)-or(S)-form] 2,2'-diethynyl-1,1'-binaphthyl was described.2,2'-Diethynyl-1,1'-binaphthyl was synthesized from binapythol by esterification of hydroxyl,Kumada reaction of sulfonic ester with Grignard reagent,bromination of methyl,hydrolyzation of dibromomethyl and especial Wittig reaction.
In the third chapter,three-dimensional cage-like cyclophanes 76 were designed and synthesized from enantiopure[(R)-or(S)-form]2,2'-diethynyl(dihydroxy)-1, 1'-binaphthyl,However we have not been given to benzene for the plane of target compounds and got a strange three-dimensional,cage-like cyclophanes.And in the process of synthetic routes involved reaction of several types:Sonogashira reaction, Sealed-tube reaction and Eglinton coupling reaction.
In the forth chapter,we solved the problem of steric hindrance in the third chapter. Through the CPK model of the Chem3D molecular modeling and simulation,we design a three-dimensional compound 91 with an extension trigeminal benzene-acetylene as a flat connecting bridge,three-dimensional cage-like cyclophanes 94 were designed and synthesized though Eglinton coupling reaction from enantiopure[(R)-or(S)-form]2,2'-diethynyl(dihydroxy)-1,1'-binaphthyl.
All the intermediates and target compounds synthesized in this paper were characterized by MS,IR,~1H NMR,~(13)C NMR and DEPT
引文
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