Synthesis, Crystal Structure and Biological Activity of 1,5-Bis(4-methoxyphenyl)-3-(4-methyl-1,2,3-thiadiazol-5-yl)pentane-1,5-dione  

作　　者：毛武涛 国丹丹 范志金 谷希树 宋海斌 王盾 范谦 Kalinina Tatiana Yury Yu.Morzherin Vasiliy A.Bakulev 

机构地区：[1]Department of Chemistry,School of Science,Tianjin University [2]State Key Laboratory of Elemento-organic Chemistry,Nankai University [3]Institute of Plant Protection,Tianjing Academy of Agricultural Sciences [4]Sichuan Functional Heterocyclic Compounds Engineering Technology Research Center,Lier Chemicals Co.,Ltd. [5]The Ural Federal University Named after the First President of Russia B. N. Yeltsin

出　　处：《Chinese Journal of Structural Chemistry》2013年第3期357-362,共6页结构化学（英文）

基　　金：funded in part by the NNSFC (20872071);the NSF of Tianjin (10JCZDJC17500);the National Key Project for Basic Research(2010CB126105);National Key Technology Research and Development Program (2011BAE06B02 and 2011BAE06B05);the Foundation of Achievements Transformation and Application of Tianjin Agricultural Science and Technology (201002250);Tianjin Key Technology Research and Development Program (11ZCGYNC00100)

摘　　要：The title compound 1,5-bis（4-methoxyphenyl）-3-（4-methyl-1,2,3-thiadiazol-5-yl）-pentane-1,5-dione （C22H22N2O4S, Mr=410.49） has been synthesized by the reaction of 4-methyl-1,2,3-thiadiazole-5-carbaldehyde with 4-methoxyacetophenone, and its structure was characterized by IR, 1H NMR, H RMS, elemental analysis and single-crystal X-ray diffraction. The crystal of the title compound belongs to monoclinic, space group P21/c with a=11.159（3）, b=9.002（3）, c=20.192（6）, β=93.393（5）°, Z=4, V=2024.6（10） 3 , Dc=1.347 g/cm3 , μ=0.191 mm-1 , F（000）=864, R=0.0333 and wR （I〉2σ （I））=0.0840. In this molecule, the 1,2,3-thiadiazol ring is nearly vertical with both phenyl rings, and intermolecular weak hydrogen bonds of C-H…O and C-H…N types together with π-π stacking interactions and interactions between S（1）…N（2） are observed. The above three kinds of interactions extend the molecules into a two-dimensional layer framework. The preliminary biological test showed that the title compound had fungicidal activity.The title compound 1,5-bis（4-methoxyphenyl）-3-（4-methyl-1,2,3-thiadiazol-5-yl）-pentane-1,5-dione （C22H22N2O4S, Mr=410.49） has been synthesized by the reaction of 4-methyl-1,2,3-thiadiazole-5-carbaldehyde with 4-methoxyacetophenone, and its structure was characterized by IR, 1H NMR, H RMS, elemental analysis and single-crystal X-ray diffraction. The crystal of the title compound belongs to monoclinic, space group P21/c with a=11.159（3）, b=9.002（3）, c=20.192（6）, β=93.393（5）°, Z=4, V=2024.6（10） 3 , Dc=1.347 g/cm3 , μ=0.191 mm-1 , F（000）=864, R=0.0333 and wR （I〉2σ （I））=0.0840. In this molecule, the 1,2,3-thiadiazol ring is nearly vertical with both phenyl rings, and intermolecular weak hydrogen bonds of C-H…O and C-H…N types together with π-π stacking interactions and interactions between S（1）…N（2） are observed. The above three kinds of interactions extend the molecules into a two-dimensional layer framework. The preliminary biological test showed that the title compound had fungicidal activity.

关 键 词：X-ray diffraction crystal structure SYNTHESIS 1 2 3-thiadiazole fungicidal activity 

分 类 号：O621.3[理学—有机化学]