基于消除反应构筑碳碳重键的一锅合成方法研究
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摘要
碳碳重键化合物在有机化学、应用化学及其它相关学科中具有重要地位。因此,探索新的构筑碳碳重键的方法具有重要的理论和实际意义。一锅合成法是一种资源节约和环境友好的方法,它具有过程简化、总产率较高以及经济节省的特点,在各式各样的化合物合成中均受到合成化学家的青睐。本文以消除反应为基本反应,着重从方法学角度首先考察了由几种砜类亲核试剂与醛反应,一锅制备碳碳重键(包括带功能基的碳碳重键)化合物的合成战略,并在此基础上探讨了一些重要的特殊结构碳碳重键化合物的应用。
本论文主要包括以下内容:
第1章,综述了构筑碳碳重键化合物所涉及的各种类型的反应,介绍了本文中将利用消除反应一锅合成的重键化合物的用途。
第2章,在亲核加成、亲核取代、消除等基本反应基础上,提出了合成甲硫芳炔类化合物的一锅合成策略。利用亲核硫型试剂甲硫甲基苯基砜(methylthiomethyl phenyl sulfone, MP-S)与芳香醛进行组合,成功地一锅合成了一系列甲硫芳炔类化合物。还通过对反应中各阶段生成的中间体的捕捉及结构分析,考察了甲硫芳炔类化合物的形成机制。结果表明,一锅合成反应经历了含有两个离去基团中间体的形成和后续的两次消除过程。该方法原料易得,操作简单,可得到较好的产率(>70%)。此外,反应还具有副产物少、容易分离和纯化的优点。
第3章,本章介绍了一锅法得到的甲硫芳基乙炔类化合物应用方面的扩展,将1-甲硫基-(4-碘)苯乙炔与各种芳炔砌块进行组合,设计并合成了一些几何形状、尺度大小、功能基数目相异以及具有π共轭体系的新颖的多头官能基芳炔硫醚类化合物,在此基础上考察了它们在纳米团簇组装过程中的应用和特殊性能。
第4章,描述了一种合成1-芳基丙炔的新方法。详细考察了该反应过程中各步骤的反应条件,建立了双消除法一锅制备1-芳基丙炔的合成策略。利用甲基苯基砜与芳香醛进行一锅反应,成功地合成了一系列1-芳基丙炔化合物。该方法具有操作简单、原料易得的优点,而且一些含有卤原子、醚键和杂环的化合物以及含有两个丙炔基的化合物也可以通过此法来合成。
第5章,提供了制备共轭烯炔类化合物的一种新方法。提出了消除法的一锅合成思想,确立了一锅法的合成路线。在1,3-二甲基-四氢-2-嘧啶酮(DMPU)存在下,利用第4章合成的1-芳基丙炔化合物与醛作用,通过新的离去基的形成,然后经历消除反应成功地制备出了几种共轭芳基烯炔类化合物。对这些化合物进行初步的光谱学考察。
第6章,描述一种构建碳碳重键的简便方法,以苄基砜为原料,在碱作用下其先发生两分子间亲核取代随之发生消除反应一锅合成出了双键化合物。在此基础上利用该合成方法成功地制备了挑战性螺旋环状化合物。并对该螺旋环状分子结构进行光谱学确证。
综上所述,本文以消除反应为基本反应,提出了制备一些重要结构重键化合物的一锅合成思想。通过合成路线设定,反应条件探索及中间体捕捉和分析并进一步合成了一些重要的含有重键的化合物。这些为构筑碳碳重键化合物提供的新方法学研究,不仅丰富了有机化学内容,对于重键化合物在材料化学和应用化学中的应用亦具有重要意义。
Carbon-Carbon multiple-bond compounds is playing an important role in organic chemistry, applied chemistry and related fields. So it is academic and practical significance to explored new methods for constructing carbon-carbon multiple-bond. By taking advantage of simplified process, higher total yield and economical operation, one-pot synthesis process acts a procedure with resource-saving and environment friendly, which have caught the eyes of synthesis chemists thus be used to synthesize various compounds. In this dissertation, elimination protocol was employed as a basal route, so a new strategy was developed to construct multiple-bond (including multiple-bond with functional group) via one-pot process by examineing some sulfones reaction with aldehydes. And the application of some Carbon-Carbon multiple-bond compounds with especial structure was explored.
This dissertation consists of six parts and is described in below contents.
Chapter 1, Various reactions for construction of multiple-bond compounds and the application of some target moleculars were firstly subjected to review.
Chapter 2, Based on nucleophilic addition, nucleophilic substitution and elimination reaction, one-pot procedure for synthesizing Methylthio aromatic acetylenes was presented. And reaction with methylthiomethyl phenyl sulfone(MP-S) and aryl aldehyde then through double elimination procedure have furnished an array of methylthio aromatic acetylenes in good yield. By capturing and identifying the structures of intermediates which generated from reaction process, the postulated mechanism of one-pot double elimination protocol was examined. The results showed one-pot procedure contained the formation of intermediate which borne two leaving groups and double elimination process of these two leaving groups. The advantages of present protocol are facile availability of starting materials, easy operation and higher yield, besides of fewer byproduct and efficient purification of the target products.
Chapter 3, the extended application of several methylthio aromatic acetylenes obtained by one-pot procedure was discussed here. Multidentate thioether molecules with different size, shape, functional groups andπ-conjugated bone were designed and synthesized. So their application in the evolution to mediate the assembly with gold nanoparticle and then appeared special property were examined.
Chapter 4, a new protocol for synthesis of (1-propynyl)arenes was discussed. The synthesis methodology to (1-propynyl)arenes through one-pot double elimination procedure was developed based on detailed exploration of the reaction condition of each step. So reaction with methyl phenyl sulfone and aryl aldehyde then through a double elimination procedure have afforded an array of (1-propynyl)arenes in moderate to excellent yield. The virtues of present protocol are facile available starting materials, easy operation. And some products with a variety of functional groups such as halogen, ether, heteroaromatic and some compounds borne two 1-propynyl groups were synthesized via this protocol.
Chapter 5, a new process for synthesis of enynes was presented here. Firstly, the idea of one-pot elimination procedure was presented and then the synthesis route to enynes via one-pot elimination procedure was established. Employment of N,N-dimethyl-propyleneurea(DMPU) as additive agent, several enynes have been synthesized via one-pot procedure which consisted of reaction of (1-propynyl)arenes which were obtained in the chart 4 with aldehyde, formation of intermediate of new leaving group and elimination process of the leaving group, and the preliminary spectral examination of these compounds was presented here.
Chapter 6, a new protocol for construction of double-bond was presented here. Benzyl sulfones undergo the process of intermolecular nucleophilic substitution and elimination reaction to give double-bond compounds. On the basis of this protocol, helical cyclophane was prepared via the designed one-pot protocol. And the structure of helical cyclophane was identified by spectral examination.
In conclusion, elimination reaction was employed as the basic protocol and the idea of one-pot synthesis procedure to prepare some multiple-bond compounds with important structure. Some important were synthesized via this protocol based on the modification by redesigning synthesis route, exploring reaction conditions and reagents, capturing and identifying the intermediates, so one-pot elimination protocol was developed to construct Carbon-Carbon multiple-bond. This protocol for synthesis of multiple-bond compound will enrich the contents of organic chemistry and it is significance of the application of compounds in material chemistry and applied chemistry.
本论文主要包括以下内容:
第1章,综述了构筑碳碳重键化合物所涉及的各种类型的反应,介绍了本文中将利用消除反应一锅合成的重键化合物的用途。
第2章,在亲核加成、亲核取代、消除等基本反应基础上,提出了合成甲硫芳炔类化合物的一锅合成策略。利用亲核硫型试剂甲硫甲基苯基砜(methylthiomethyl phenyl sulfone, MP-S)与芳香醛进行组合,成功地一锅合成了一系列甲硫芳炔类化合物。还通过对反应中各阶段生成的中间体的捕捉及结构分析,考察了甲硫芳炔类化合物的形成机制。结果表明,一锅合成反应经历了含有两个离去基团中间体的形成和后续的两次消除过程。该方法原料易得,操作简单,可得到较好的产率(>70%)。此外,反应还具有副产物少、容易分离和纯化的优点。
第3章,本章介绍了一锅法得到的甲硫芳基乙炔类化合物应用方面的扩展,将1-甲硫基-(4-碘)苯乙炔与各种芳炔砌块进行组合,设计并合成了一些几何形状、尺度大小、功能基数目相异以及具有π共轭体系的新颖的多头官能基芳炔硫醚类化合物,在此基础上考察了它们在纳米团簇组装过程中的应用和特殊性能。
第4章,描述了一种合成1-芳基丙炔的新方法。详细考察了该反应过程中各步骤的反应条件,建立了双消除法一锅制备1-芳基丙炔的合成策略。利用甲基苯基砜与芳香醛进行一锅反应,成功地合成了一系列1-芳基丙炔化合物。该方法具有操作简单、原料易得的优点,而且一些含有卤原子、醚键和杂环的化合物以及含有两个丙炔基的化合物也可以通过此法来合成。
第5章,提供了制备共轭烯炔类化合物的一种新方法。提出了消除法的一锅合成思想,确立了一锅法的合成路线。在1,3-二甲基-四氢-2-嘧啶酮(DMPU)存在下,利用第4章合成的1-芳基丙炔化合物与醛作用,通过新的离去基的形成,然后经历消除反应成功地制备出了几种共轭芳基烯炔类化合物。对这些化合物进行初步的光谱学考察。
第6章,描述一种构建碳碳重键的简便方法,以苄基砜为原料,在碱作用下其先发生两分子间亲核取代随之发生消除反应一锅合成出了双键化合物。在此基础上利用该合成方法成功地制备了挑战性螺旋环状化合物。并对该螺旋环状分子结构进行光谱学确证。
综上所述,本文以消除反应为基本反应,提出了制备一些重要结构重键化合物的一锅合成思想。通过合成路线设定,反应条件探索及中间体捕捉和分析并进一步合成了一些重要的含有重键的化合物。这些为构筑碳碳重键化合物提供的新方法学研究,不仅丰富了有机化学内容,对于重键化合物在材料化学和应用化学中的应用亦具有重要意义。
Carbon-Carbon multiple-bond compounds is playing an important role in organic chemistry, applied chemistry and related fields. So it is academic and practical significance to explored new methods for constructing carbon-carbon multiple-bond. By taking advantage of simplified process, higher total yield and economical operation, one-pot synthesis process acts a procedure with resource-saving and environment friendly, which have caught the eyes of synthesis chemists thus be used to synthesize various compounds. In this dissertation, elimination protocol was employed as a basal route, so a new strategy was developed to construct multiple-bond (including multiple-bond with functional group) via one-pot process by examineing some sulfones reaction with aldehydes. And the application of some Carbon-Carbon multiple-bond compounds with especial structure was explored.
This dissertation consists of six parts and is described in below contents.
Chapter 1, Various reactions for construction of multiple-bond compounds and the application of some target moleculars were firstly subjected to review.
Chapter 2, Based on nucleophilic addition, nucleophilic substitution and elimination reaction, one-pot procedure for synthesizing Methylthio aromatic acetylenes was presented. And reaction with methylthiomethyl phenyl sulfone(MP-S) and aryl aldehyde then through double elimination procedure have furnished an array of methylthio aromatic acetylenes in good yield. By capturing and identifying the structures of intermediates which generated from reaction process, the postulated mechanism of one-pot double elimination protocol was examined. The results showed one-pot procedure contained the formation of intermediate which borne two leaving groups and double elimination process of these two leaving groups. The advantages of present protocol are facile availability of starting materials, easy operation and higher yield, besides of fewer byproduct and efficient purification of the target products.
Chapter 3, the extended application of several methylthio aromatic acetylenes obtained by one-pot procedure was discussed here. Multidentate thioether molecules with different size, shape, functional groups andπ-conjugated bone were designed and synthesized. So their application in the evolution to mediate the assembly with gold nanoparticle and then appeared special property were examined.
Chapter 4, a new protocol for synthesis of (1-propynyl)arenes was discussed. The synthesis methodology to (1-propynyl)arenes through one-pot double elimination procedure was developed based on detailed exploration of the reaction condition of each step. So reaction with methyl phenyl sulfone and aryl aldehyde then through a double elimination procedure have afforded an array of (1-propynyl)arenes in moderate to excellent yield. The virtues of present protocol are facile available starting materials, easy operation. And some products with a variety of functional groups such as halogen, ether, heteroaromatic and some compounds borne two 1-propynyl groups were synthesized via this protocol.
Chapter 5, a new process for synthesis of enynes was presented here. Firstly, the idea of one-pot elimination procedure was presented and then the synthesis route to enynes via one-pot elimination procedure was established. Employment of N,N-dimethyl-propyleneurea(DMPU) as additive agent, several enynes have been synthesized via one-pot procedure which consisted of reaction of (1-propynyl)arenes which were obtained in the chart 4 with aldehyde, formation of intermediate of new leaving group and elimination process of the leaving group, and the preliminary spectral examination of these compounds was presented here.
Chapter 6, a new protocol for construction of double-bond was presented here. Benzyl sulfones undergo the process of intermolecular nucleophilic substitution and elimination reaction to give double-bond compounds. On the basis of this protocol, helical cyclophane was prepared via the designed one-pot protocol. And the structure of helical cyclophane was identified by spectral examination.
In conclusion, elimination reaction was employed as the basic protocol and the idea of one-pot synthesis procedure to prepare some multiple-bond compounds with important structure. Some important were synthesized via this protocol based on the modification by redesigning synthesis route, exploring reaction conditions and reagents, capturing and identifying the intermediates, so one-pot elimination protocol was developed to construct Carbon-Carbon multiple-bond. This protocol for synthesis of multiple-bond compound will enrich the contents of organic chemistry and it is significance of the application of compounds in material chemistry and applied chemistry.
引文
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