新型炔基胺大环化合物的构造及其高阶分子堆积结构

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英文题名：Construction of New Macrocyclic Compounds Possessing Propargylamine Skeleton and Study of Their Higher-order Crystal Packing 副题名：超分子三螺旋体的研究 英文副题名：Supramolecular Triple Helix 作者：庞韬 论文级别：博士 学科专业名称：有机化学 中文关键词：大环化合物 ; 炔基胺骨架 ; 不对称大环化合物 ; 多官能团产物 ; 双环化 ; 三螺旋体 ; 螺环化合物 英文关键词：macrocyclic compound ; propargylamine skeleton ; asymmetric macrocycle ; multifunctional product ; bicyclization ; triple helix ; Spiro compound 学位年度：2013 导师：吴安心 学科代码：070303 学位授予单位：华中师范大学 论文提交日期：2013-06-01

摘要

大环化合物在药物开发和超分子化学领域有着重要的意义,因为结合的灵活性和结构的特殊性而被称为“明星分子”。在药物开发的研究进程中,大环类药物一直是医药领域的经典研究对象；同时大环化合物又是微型分子反应器的器件,在有机催化领域得到广泛应用；此外,大环化合物是主-客体化学研究领域的重要媒介,是超分子化学的重要组成部分。大环化学的发展给无机化学,有机化学等领域带来了新的气息。而晶体工程学是分子工程学的一个重要组成部分,它涉及分子或化学基团在晶体中的组装行为、晶体的设计及结构与性能的控制,而大环化合物作为晶体结构不可或缺的一类分子模块,能呈现出许多独特的晶体组装模式。本论文研究的中心工作是将炔基胺骨架引入大环化合物中,设计和合成出一系列新型的炔基胺骨架大环结构体。同时基于炔基胺衍生物这类具有特殊拓扑结构的分子,作为开展分子组装研究的模块,去研究其在晶态堆积中的特殊结构形态。本文另一方面的工作是研究基于三元催化剂不同摩尔比例选择性调控合成不同结构的螺环化合物。
     具体内容如下：
     第一章,首先概述了近年来多种大环化合物的创新策略,并集中介绍了含有炔基的大环化合物的研究进程,由此提出了本论文的设想和研究思路。
     第二章,将双位点端炔与双位点环化仲胺通过Mannich缩合反应作为构建大环化合物的设计策略,成功合成了八个新颖的大环产物,分别是[1+2+1]型和[2+4+2]型。并且我们得到了三个[1+2+1]型产物的单晶结构和一个[2+4+2]型产物的单晶结构。
     第三章,我们分别用一个不对称的双端炔底物和三个不对称的双位点仲胺为底物参与反应,成功合成了八个不对称的大环产物。并得到了一个[2+4+2]型产物的单晶结构。
     第四章,我们集成Mannich缩合反应和炔炔偶联反应于一锅的自序化合成策略,以高哌嗪为底物,实现了三组分反应一步选择性调控高效合成同时含有炔基胺和炔炔偶联产物-联二炔骨架的多官能团化合物的目标。
     第五章,串级双环化反应是一个高效的构造复杂结构体的策略,广泛应用于复杂多环结构的天然产物的全合成中。我们以2,7-二萘酚为底物,与双位点仲胺-哌嗪和甲醛三组分反应,成功合成含有色烯骨架和炔基胺骨架的双环化产物。
     第六章,我们在研究炔基胺大环衍生物的晶态堆积过程中,发现了第一例非预期的基于大环化合物的高级组装体-四聚体构筑的超分子三螺旋体,详细的描述了其高级结构形态和自组装驱动力。
     第七章,我们在构造大环基本模块的合成中,有幸发现了第一例基于三元催化剂(GaCl3/InCl3/CuCl)摩尔比例调控选择性合成不同结构的螺环化合物。经过对实验条件的探讨,我们发现,当三元催化剂的摩尔比例为：GaCl3:InCl3:CuCl=1.75:1:1时,我们选择性地合成萘酮螺萘并吡喃产物,而当催化剂摩尔比例换为GaCl3:InCl3:CuCl=1.5:0.75:1时,则选择性地合成萘酮螺萘并呋喃产物。
     第八章,对本篇博士论文的工作进行了总结和展望。
Macrocycles are of high significance in areas as diverse as drug development and supramolecular chemistry. They can be considered as "privileged molecules" because they can combine flexibility and conformational bias. Macrocyclic structures were identified as classic objects of study existing not only in drug development, but also in areas as diverse as material sciences. In addition, macrocyclic compounds were widely applied in organic catalysis as tiny molecular reactors. Moreover, special highlights in great significance of macrocyclic compounds as the medium in host-guest chemistry, it is also an important part of supramolecular chemistry. The development of macrocycles chemistry brings inorganic chemistry and organic chemistry a special highlight. Besides, the crystal engineering is an important section of the molecular engineering, which involves the assembly behavior of molecules or chemical groups in crystal, the design of crystal and the control of the structure and function. The propargylamine backbone was introduced in macrocyclic compound which is the central theme of this work; we designed and synthesized a series of novel macrocycle with propargylamine scaffolds by introducing the propargylamine backbones into this macrocyclic compounds in this thesis. And then this special structures in the crystal were also studied based on the propargylamine derivative being a molecular assembly module which has special molecular topology.
     Another part of this thesis focuses on the selective synthesis of six-membered and five-membered spironaphthalenones by controlling the molar ratio of ternary Ga-In-Cu catalysts.
     The main contents are shown as following:
     In chapter1, the innovative strategies to synthesize macrocycle in recent years were reviewed. The research progress of macrocyclic compounds containing alkynyl group were focused on detailly. Then we put forward our research topics based on the idea of mentioned above.
     In chapter2, the design strategy to construct macrocycles architecture was applied in macrocyclic compounds via Mannich condensation reaction using the two sites of terminal alkynes and double sites of secondary amines; we successfully designed and synthesized eight novel macrocycles containing the series of [1+2+1] type and [2+4+2] type. The single-crystal structures of three [1+2+1] type products and a [2+4+2] type product were obtained.
     In chapter3, eight asymmetric macrocycles were synthesized successfully starting from combining a asymmetric double terminal alkyne with three asymmetric double sites of secondary amine as substrates. The single-crystal structure of [2+4+2] type product was obtained.
     In chapter4, we integrated Mannich condensation reaction and cross-coupling reaction of alkynes in one-pot in this part of the thesis. The polyfunctional macrocycle containing propargylamine and coupling products of alkynes to alkynes and diyne skeletons were synthesized in one-pot by three-component reaction. It is selectively controllable and highly efficient using homopiperazine as a substrate.
     In chapter5, bicyclization reaction played a key role in total synthesis of polycyclic compound on account of high-efficiency. We achieved the objective of bicyclization-macrocycles possessing both propargylamine and chromene skeletons from naphthalene-2,7-terminal dialkyne, piperazine and formaldehyde via three-component reaction. The synthetic strategies of a cascade bicyclization reaction with a high efficiency especially applied in total synthesis of natural products were used to construct complicated macrocycles. We used2,7-dinaphthol and two sites of secondary amine--piperazine and formaldehyde as substrates to realize the three-component reaction. Bicyclic products containing chromene skeleton and alkynyl amine skeleton were obtained successfully in one-pot.
     In chapter6, the unexpected triple helix was firstly discovered based on the tetrameric assembly of a macrocycle during the study of the packing the crystalline structure of the macrocycle derivatives containing propargylamine skeletons. And the senior structural form and self-assembly driving force were described detailedly.
     In chapter7, six-membered and five-membered spironaphthalenones were firstly synthesized selectively by controlling the molar ratio of ternary catalysts during the construction of macrocyclic basic module. The reaction conditions were optimized by adjusting the molar ratio of GaCl3/InCl3/CuCl, additives, reaction temperature and time. Six-membered spironaphthalenone was selectively obtained as the only product when the molar ratio of catalyst GaCl3:InCl3:CuCl=1.75:1:1. When the catalyst molar ratio of GaCl3/InCl3/CuCl was changed to1.5:0.75:1, the five-membered spironaphthalenon was selectively synthesized.
     In chapter8, the summary and prospects of this thesis were given.

引文

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