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有机化学
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有机化学 ›› 2004, Vol. 24 ›› Issue (12): 1622-1625. 上一篇    下一篇

研究简报

3,6-二苯基-1,2-二氢-1,2,4,5-四嗪-1,2-二甲酸乙酯的合成和晶体结构

饶国武, 胡惟孝*   

  1. 浙江工业大学药学院 浙江 杭州 310014
  • 收稿日期:2003-12-08 修回日期:2004-06-22 接受日期:2004-06-22 发布日期:2022-09-20

Synthesis and Crystal Structure of Diethyl 3,6-Diphenyl-1,2-dihydro- 1,2,4,5-tetrazine-1,2-dicarboxylate

RAO Guo-Wu, HU Wei-Xiao*   

  1. College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014
  • Received:2003-12-08 Revised:2004-06-22 Accepted:2004-06-22 Published:2022-09-20
  • Contact: *E-mail: ygwang@mail.ccnu.edu.cn

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氯甲酸乙酯和3,6-二苯基-1,2-二氢-1,2,4,5-四嗪反应生成的是标题化合物3,6-二苯基-1,2-二氢-1,2,4,5-四嗪-1,2-二甲酸乙酯,而不是预期的3,6-二苯基-1,4-二氢-1,2,4,5-四嗪-1,4-二甲酸乙酯,其结构通过X射线单晶结构分析得以证实.此晶体属三斜晶系,P-1空间群,晶胞参数分别为:a=0.8915(2) nm,b=1.0444(2) nm, c=1.1509(3) nm, α=103.268(3)°, β=102.844(3)°, γ=100.765(3)°, Z=2, R1=0.0593和wR2=0.1691.结果表明该化合物中心六元环的2,3-二氮杂丁二烯基团不共平面,没有很好地共轭.且该化合物中心六元环呈扭式构象,N(1)和N(2)原子分别偏离环平面-0.03611(41)和0.02944(40) nm.

关键词: 1,2,4,5-四嗪, 晶体结构, 共轭, 扭式构象

The reaction of ethyl chloroformate with 3,6-diphenyl-1,2-dihydro-1,2,4,5-tetrazine gave the title compound, diethyl 3,6-diphenyl-1,2-dihydro-1,2,4,5-tetrazine-1,2-dicarboxylate, rather than the expected diethyl 3,6-diphenyl-1,4-dihydro-1,2,4,5-tetrazine-1,4-dicarboxylate. The structure of the title compound was determined by X-ray diffraction analysis. Thetitle compound crystallized in triclinic system with space group P-1, a=0.8915(2) nm, b=1.0444(2) nm, c=1.1509(3) nm, α=103.268(3)°, β=102.844(3)°, γ=100.765 (3)°, Z=2, R1=0.0593, and wR2=0.1691. The 2,3-diazabutadiene group in the central six-membered ringisnot coplanar, indicating a lack of conjugation. The ring has a twisted conformation, in which adjacent atoms N(1) and N(2) deviate from the plane of the ring by -0.03611(41) and 0.02944(40) nm, respectively.

Key words: 1,2,4,5-tetrazine, crystal structure, conjugation, twisted conformation