2-[5-amino-1-(2-chloroethyl)-1H-imidazol-4-ylmethylene]-malononitrile | 810660-39-0

• 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-[5-amino-1-(2-chloroethyl)-1H-imidazol-4-ylmethylene]-malononitrile
• 英文别名: 2-[[5-Amino-1-(2-chloroethyl)imidazol-4-yl]methylidene]propanedinitrile
• CAS: 810660-39-0
• 化学式: C₉H₈ClN₅
• 分子量: 221.649
• InChiKey: UNGSTZHYVPSTFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  91.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[5-amino-1-(2-chloroethyl)-1H-imidazol-4-ylmethylene]-malononitrile 在 sodium ethanolate 、 碳酸氢钠 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 生成 5-amino-3-vinyl-3H-imidazo[4,5-b]pyridine-6-carbonitrile
  参考文献：
  名称：

  Routes toN-vinyl-nitroimidazoles andN-vinyl-deazapurines

  摘要：

  AbstractThe preparations of 4‐ and 5‐nitro‐1‐vinylimidazole (2 and 7) are described. Selective reduction of the nitro group using Fe/dil.HCl is achieved for the 4‐nitro derivative but this is not effective when ethoxymethylenemalononitrile is used to trap the amine. For 5‐nitroimidazole studies the N‐vinyl substituent is kept masked as a 2‐chloroethyl group, which remains unchanged during catalytic reduction of the nitro function (Pd/C), and is revealed by HCl elimination at a later stage. In this way, the 1‐deazapurine 13 and the tricyclic derivative 14 have been prepared.

  DOI：

  10.1002/jhet.5570410508
• 作为产物：
  描述：

  1-(2-氯乙基)-5-硝基-1H-咪唑 在 palladium on activated charcoal 氢气 作用下， 以 1,4-二氧六环 为溶剂， 生成 2-[5-amino-1-(2-chloroethyl)-1H-imidazol-4-ylmethylene]-malononitrile
  参考文献：
  名称：

  Routes toN-vinyl-nitroimidazoles andN-vinyl-deazapurines

  摘要：

  AbstractThe preparations of 4‐ and 5‐nitro‐1‐vinylimidazole (2 and 7) are described. Selective reduction of the nitro group using Fe/dil.HCl is achieved for the 4‐nitro derivative but this is not effective when ethoxymethylenemalononitrile is used to trap the amine. For 5‐nitroimidazole studies the N‐vinyl substituent is kept masked as a 2‐chloroethyl group, which remains unchanged during catalytic reduction of the nitro function (Pd/C), and is revealed by HCl elimination at a later stage. In this way, the 1‐deazapurine 13 and the tricyclic derivative 14 have been prepared.

  DOI：

  10.1002/jhet.5570410508