N-<4(5)-(m-Nitrophenyl)-1H-imidazol-2-yl>acetamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-<4(5)-(m-Nitrophenyl)-1H-imidazol-2-yl>acetamide
• 英文别名: N-[5-(3-nitrophenyl)-1H-imidazol-2-yl]acetamide
• 化学式: C₁₁H₁₀N₄O₃
• 分子量: 246.225
• InChiKey: JTCJARCVJULYBE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-<4(5)-(m-Nitrophenyl)-1H-imidazol-2-yl>acetamide 在 硫酸 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 以73%的产率得到2-Amino-4(5)-(m-nitrophenyl)imidazole sulfate
  参考文献：
  名称：

  A Simple and Practical Synthesis of 2-Aminoimidazoles

  摘要：

  A new and simple two-step procedure to synthesize 2-aminoimidazoles (2-AI's) from readily available materials has been developed. The cyclization reaction of alpha-halo ketones and N-acetylguanidine in acetonitrile (MeCN) at reflux, or in dimethylformamide (DMF) at ambient temperature, gives 4(5)-substituted and 4,5-disubstituted N-(1H-imidazol-2-yl)acetamides, which are then hydrolyzed to their respective 2-AI's. In general, the purified products were isolated in good yields. We have prepared several examples and have demonstrated the usefulness of this method by its application in the total synthesis of 8, an interesting histamine analog, and oroidin, 15, a marine natural product isolated from various sponges.

  DOI：

  10.1021/jo00103a021
• 作为产物：
  描述：

  2-溴-3'-硝基苯乙酮 、 N-乙酰基胍 以 N,N-二甲基甲酰胺 为溶剂， 反应 96.0h， 以41%的产率得到N-<4(5)-(m-Nitrophenyl)-1H-imidazol-2-yl>acetamide
  参考文献：
  名称：

  A Simple and Practical Synthesis of 2-Aminoimidazoles

  摘要：

  A new and simple two-step procedure to synthesize 2-aminoimidazoles (2-AI's) from readily available materials has been developed. The cyclization reaction of alpha-halo ketones and N-acetylguanidine in acetonitrile (MeCN) at reflux, or in dimethylformamide (DMF) at ambient temperature, gives 4(5)-substituted and 4,5-disubstituted N-(1H-imidazol-2-yl)acetamides, which are then hydrolyzed to their respective 2-AI's. In general, the purified products were isolated in good yields. We have prepared several examples and have demonstrated the usefulness of this method by its application in the total synthesis of 8, an interesting histamine analog, and oroidin, 15, a marine natural product isolated from various sponges.

  DOI：

  10.1021/jo00103a021