1-(p-methoxybenzyl)-2-ethynyl-4,5-dicyanoimidazole | 753003-12-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(p-methoxybenzyl)-2-ethynyl-4,5-dicyanoimidazole
• 英文别名: 2-Ethynyl-1-[(4-methoxyphenyl)methyl]-1H-imidazole-4,5-dicarbonitrile；2-ethynyl-1-[(4-methoxyphenyl)methyl]imidazole-4,5-dicarbonitrile
• CAS: 753003-12-2
• 化学式: C₁₅H₁₀N₄O
• 分子量: 262.271
• InChiKey: KMXZEBOBOJZNRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  74.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(p-methoxybenzyl)-2-ethynyl-4,5-dicyanoimidazole 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 17.0h， 生成 2-ethynyl-4,5-dicyanoimidazole
  参考文献：
  名称：

  New Acetylenic Monomers and Polymers from 4,5-Dicyanoimidazole

  摘要：

  An efficient synthesis of 1-methyl-2-ethynyl-4,5-dicyanoimidazole via Sonogashira coupling is described. Our optimized method generates 1-methyl-2-ethynyl-4,5-dicyanoimidazole in almost 80% yield from 1-methyl-2-bromo-4,5-dicyanoimidazole. Syntheses of the ethyl, propyl, and p-methoxybenzyl derivatives of 2-ethynyl-4,5-dicyanoimidazole are also reported. The polymerization of 1-methyl-2-ethynyl-4,5-dicyanoimidazole with transition-metal catalysts and triethylamine is described. Variation of catalyst concentration, reaction time, and temperature is also described. A more complete mechanistic picture of acetylene polymerizations, especially those with electron-withdrawing substituents, is presented. Solid samples of 1-methyl-2-ethynyl-4,5-dicyanoimidazole oligomers are EPR-active, and the number of free spins was quantified. Cyclic voltammetry was used to investigate the reduction of 1-methyl-2-ethynyl-4,5-dicyanoimidazole oligomers and other dicyanoimidazole derivatives.

  DOI：

  10.1021/ma035920r
• 作为产物：
  描述：

  2-溴-4,5-二氰基咪唑 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium fluoride 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 50.0h， 生成 1-(p-methoxybenzyl)-2-ethynyl-4,5-dicyanoimidazole
  参考文献：
  名称：

  New Acetylenic Monomers and Polymers from 4,5-Dicyanoimidazole

  摘要：

  An efficient synthesis of 1-methyl-2-ethynyl-4,5-dicyanoimidazole via Sonogashira coupling is described. Our optimized method generates 1-methyl-2-ethynyl-4,5-dicyanoimidazole in almost 80% yield from 1-methyl-2-bromo-4,5-dicyanoimidazole. Syntheses of the ethyl, propyl, and p-methoxybenzyl derivatives of 2-ethynyl-4,5-dicyanoimidazole are also reported. The polymerization of 1-methyl-2-ethynyl-4,5-dicyanoimidazole with transition-metal catalysts and triethylamine is described. Variation of catalyst concentration, reaction time, and temperature is also described. A more complete mechanistic picture of acetylene polymerizations, especially those with electron-withdrawing substituents, is presented. Solid samples of 1-methyl-2-ethynyl-4,5-dicyanoimidazole oligomers are EPR-active, and the number of free spins was quantified. Cyclic voltammetry was used to investigate the reduction of 1-methyl-2-ethynyl-4,5-dicyanoimidazole oligomers and other dicyanoimidazole derivatives.

  DOI：

  10.1021/ma035920r