香豆素衍生物的合成及结构表征

doi:10.7517/j.issn.1674-0475.2008.05.393

影像科学与光化学 ›› 2008, Vol. 26 ›› Issue (5): 393-402.DOI: 10.7517/j.issn.1674-0475.2008.05.393

香豆素衍生物的合成及结构表征

孙一峰¹, 马世营¹, 张东娣², 程学礼¹

1. 泰山学院, 化学系, 山东, 泰安271021;
2. 河南大学药学院, 河南, 开封475002

收稿日期:2008-01-02 修回日期:2008-03-13 出版日期:2008-09-23 发布日期:2008-09-23
通讯作者: 孙一峰(1967- ),男,博士,副教授,主要从事有机功能材料和药物合成研究,E-mail:sunyf50@yahoo.com.cn.
基金资助:
泰山学院科研基金资助项目(Y04-2-02)

Synthesis and Structure Characterization of Coumarin Derivatives

SUN Yi-feng¹, MA Shi-ying¹, ZHANG Dong-di², CHENG Xue-li¹

1. Department of Chemistry, Taishan University, Taian 271021, Shandong, P. R. China;
2. College of Pharmacy, Henan University, kaifeng 475002, Henan, P. R. China

Received:2008-01-02 Revised:2008-03-13 Online:2008-09-23 Published:2008-09-23

摘要/Abstract

摘要： 合成了11个香豆素衍生物,产率53%—79%,利用元素分析、MS和¹HNMR对其结构进行了表征.同时,由2-氨基苯并噻唑(ABT)和8-甲氧基香豆素-3-甲酸乙酯(MCC)合成了给体-受体加合物ABT-MCC,通过X射线单晶衍射法测定了其晶体结构,晶体属三斜晶系,P1空间群,晶胞参数为:a=9.5978(19)Å,b=10.686(2)Å,c=10.693(2)Å,α=71.30(3)°,β=70.43(3)°,γ=88.99(3)°,V=973.9(3)Å³,Z=2,D_x=1.359 mg/m³,μ=0.200 mm^-1,F(000)=416,R=0.0463,wR=0.0992.结果表明,在ABT-MCC晶体中,分子间通过N—H…N和N—H…O氢键作用形成对称的A…D…D′…A′氢键四聚体,并通过弱的C—H…O氢键连接成为一维超分子链状结构,进而分子间通过π-π堆积作用形成层状结构.

关键词: 香豆素衍生物, 2-氨基苯并噻唑, 给体-受体加合物, 晶体结构

Abstract: Eleven new coumarin derivatives were prepared in 53% to 79% yields.The structures of the title compounds were characterized by elemental analysis,¹HNMR and MS.The crystal structure of donor-acceptor complex ABT-MCC derived from 2-amino-1,3-benzothiazole(ABT) and ethyl 8-mthoxycoumarin-3-carboxylate(MCC) was determined by X-ray diffraction analysis.The crystal of ABT-MCC belongs to the triclinic system,space group P1,cell parameters: a=9.5978(19)Å,b=10.686(2)Å,c=10.693(2)Å,α=71.30(3)°,β=70.43(3)°,γ=88.99(3) °,V=973.9(3)Å³,Z=2,D_x=1.359 mg/m³,μ=0.200 mm^-1,F(000)=416,R=0.0463, wR=0.0992.X-ray diffraction reveals that the complex shows the A…D…D’…A’ H-bonded tetramer.The molecules are connected via intermolecular hydrogen bonds into a one-dimensional chain structure,and are further assembled to form a layer structure via the π-π stacking.

Key words: coumarin derivatives, 2-aminobenzothiazole, donor-acceptor complex, synthesis, crystal structure

中图分类号:

孙一峰, 马世营, 张东娣, 程学礼. 香豆素衍生物的合成及结构表征[J]. 影像科学与光化学, 2008, 26(5): 393-402.

SUN Yi-feng, MA Shi-ying, ZHANG Dong-di, CHENG Xue-li. Synthesis and Structure Characterization of Coumarin Derivatives[J]. Imaging Science and Photochemistry, 2008, 26(5): 393-402.

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香豆素衍生物的合成及结构表征

Synthesis and Structure Characterization of Coumarin Derivatives

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