2-(2,2-dibromovinyl)-1-methyl-1H-imidazole-4,5-dicarbonitrile | 1226622-39-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(2,2-dibromovinyl)-1-methyl-1H-imidazole-4,5-dicarbonitrile
• 英文别名: 2-(2,2-Dibromovinyl)-1-methyl-1h-imidazole-4,5-dicarbonitrile；2-(2,2-dibromoethenyl)-1-methylimidazole-4,5-dicarbonitrile
• CAS: 1226622-39-4
• 化学式: C₈H₄Br₂N₄
• 分子量: 315.955
• InChiKey: VHIBIQDVPZNSHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  65.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2,2-dibromovinyl)-1-methyl-1H-imidazole-4,5-dicarbonitrile 、 4-二甲基氨基苯乙炔 在 copper(l) iodide 、 bis(triphenylphosphine)palladium(II) dichloride 作用下， 以 四氢呋喃 、 三乙胺 为溶剂， 反应 2.0h， 以96%的产率得到2-(4-(4-(N,N-dimethylamino)phenyl)-2-((4-(N,N-dimethylamino)phenyl)ethynyl)but-1-en-3-ynyl)-1-methyl-1H-imidazole-4,5-dicarbonitrile
  参考文献：
  名称：

  Branched charge-transfer chromophores featuring a 4,5-dicyanoimidazole unit

  摘要：

  Six branched and stable push-pull chromophores featuring 4,5-dicyanoimidazole as an acceptor moiety, an N,N-dimethylamino group as a donor and various pi-conjugated linkers are reported. Systematic extension of the pi-linker revealed that the optical and electrochemical properties of A-pi-D chromophores are mainly affected by the nature of the pi-conjugated backbone (length and planarity) as well as by the number of appended donors. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.02.067
• 作为产物：
  描述：

  四溴化碳 、 2-formyl-1-methyl-1H-imidazole-4,5-dicarbonitrile 在 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以92%的产率得到2-(2,2-dibromovinyl)-1-methyl-1H-imidazole-4,5-dicarbonitrile
  参考文献：
  名称：

  Crystal Structure of 2-(2,2-Dibromovinyl)-1-methyl-1H-imidazole-4,5-dicarbonitrile

  摘要：

  2-(2,2-二溴乙烯基)-1-甲基-1H-咪唑-4,5-二腈（C8H4Br2N4，分子量315.92）的晶体结构已通过单晶X射线衍射分析确定。该化合物在单斜晶系中结晶，空间群为P21/c，晶胞参数为：a=15.144(2)Å，b=16.382(3)Å，c=8.267(1)Å，β=95.76(2)°，Z=8。2505个观察到的反射的最终可靠性指数为0.0297。2-(2,2-二溴乙烯基)-4,5-二氰基-1-甲基咪唑的两个分子位于晶胞的独立部分。晶体堆积通过C-H·N氢键和Br·N分子间相互作用稳定。

  DOI：

  10.1007/s10870-011-0007-9

文献信息

• Branched charge-transfer chromophores featuring a 4,5-dicyanoimidazole unit
  作者：Filip Bureš、Jiří Kulhánek、Tomáš Mikysek、Jiří Ludvík、Ján Lokaj

  DOI：10.1016/j.tetlet.2010.02.067

  日期：2010.4

  Six branched and stable push-pull chromophores featuring 4,5-dicyanoimidazole as an acceptor moiety, an N,N-dimethylamino group as a donor and various pi-conjugated linkers are reported. Systematic extension of the pi-linker revealed that the optical and electrochemical properties of A-pi-D chromophores are mainly affected by the nature of the pi-conjugated backbone (length and planarity) as well as by the number of appended donors. (C) 2010 Elsevier Ltd. All rights reserved.
• Crystal Structure of 2-(2,2-Dibromovinyl)-1-methyl-1H-imidazole-4,5-dicarbonitrile
  作者：Jan Lokaj、Jan Moncol、Filip Bureš、Jiří Kulhánek

  DOI：10.1007/s10870-011-0007-9

  日期：2011.6

  The crystal structure of 2-(2,2-dibromovinyl)-1-methyl-1H-imidazole-4,5-dicarbonitrile (C8H4Br2N4, Mr = 315.92) has been determined by single crystal X-ray diffraction analysis. The compound crystallizes in the monoclinic crystal system with space group P21/c and unit cell parameters: a = 15.144(2), b = 16.382(3), c = 8.267(1) Å, β = 95.76(2)o and Z = 8. The final reliability index is 0.0297 for 2505 observed reflections. The two molecules of 2-(2,2-dibromovinyl)-4,5-dicyano-1-methylimidazole are localized in independent part of unit cell. The crystal packing is stabilized by C–H···N hydrogen bonds and Br···N intermolecular interactions.

  2-(2,2-二溴乙烯基)-1-甲基-1H-咪唑-4,5-二腈（C8H4Br2N4，分子量315.92）的晶体结构已通过单晶X射线衍射分析确定。该化合物在单斜晶系中结晶，空间群为P21/c，晶胞参数为：a=15.144(2)Å，b=16.382(3)Å，c=8.267(1)Å，β=95.76(2)°，Z=8。2505个观察到的反射的最终可靠性指数为0.0297。2-(2,2-二溴乙烯基)-4,5-二氰基-1-甲基咪唑的两个分子位于晶胞的独立部分。晶体堆积通过C-H·N氢键和Br·N分子间相互作用稳定。