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The Design and Synthesis of Novel Cyclophynes with 2, 2’-Binaphthyl Template

Author: XueHaiYan
Tutor: AnDeLie
School: Hunan University
Course: Organic Chemistry
Keywords: Cyclophane Binaphthyl template Double helicate Synthesis
CLC: O621.2
Type: Master's thesis
Year: 2008
Downloads: 28
Quote: 0
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Abstract


The synthesis of cyclophynes and their applications in various fields are reviewed in this paper based on a large number of references. After several decades’development, the chemistry of cyclophynes has become a major component of supramolecular chemistry, of molecular recognition, of the building blocks for organic catalysts, receptor models, crown ethers, cryptands and of carbon-rich chemistry. The previous work of our lab 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’- positions -1,1’-binaphthyl was used as synthetic template for the synthesis of target molecules in this paper.In the second chapter of this paper, the design and synthesis of cyclophane with unit of two ethynyls were described. Intermediates compounds 37 and 44 were synthesied from enantiopure [（R）-or（S）-form] 2-and 2’-positions of a 1,1’- binaphthalene template by introduction of protecting nitrine group, removal of protecting group, Sonogashira coupling, tube sealing and so on. In the last step,we got the target compounds 27 and 28 throught intermolecular Eglinton coupling reaction. In the intermolecular Eglinton reaction, a syringe pump that can control the dropping rate of reactant solution was used in order to avoid the high concentration of reactant. The high concentration of reactant will produce intermolecular reaction. By using the syringe pump, the yields of the last step of intermolecular Eglinton coupling reaction were greatly improved.In the third chapter, compounds of double helical structure with unit of two ethynyls were designed and synthesized. First, important intermediate compounds 57 and 65 were synthesized from binaphthyl by the introduction of protecting group and the conneting of linking bridges , then target compounds 29 and 30 were got throught intermolecular Eglinton coupling reactionThe structures of the new intermediates and target molecules were identified by 1H NMR, 13C NMR, DEPT, IR. To further study of their properties, the UV-Vis and circular dichroism （CD） spectra of the target compounds were measured.

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CLC: > Mathematical sciences and chemical > Chemistry > Organic Chemistry > Organic Chemistry general issues > Properties of organic compounds
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