2-Amino-4(5)-(p-bromophenyl)imidazole sulfate | 1177346-50-7

• 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-Amino-4(5)-(p-bromophenyl)imidazole sulfate
• 英文别名: 5-(4-bromophenyl)-1H-imidazol-2-amine sulphate (2:1)；5-(4-bromophenyl)-1H-imidazol-2-amine;sulfuric acid
• CAS: 1177346-50-7
• 化学式: 2C₉H₈BrN₃*H₂O₄S
• 分子量: 574.253
• InChiKey: YCLUTOYTUOKYQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.77
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  138
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-<4(5)-p-Bromophenyl-1H-imidazol-2-yl>acetamide 在 硫酸 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 以58%的产率得到2-Amino-4(5)-(p-bromophenyl)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

文献信息

• A Simple and Practical Synthesis of 2-Aminoimidazoles
  作者：Thomas L. Little、Stephen E. Webber

  DOI：10.1021/jo00103a021

  日期：1994.12

  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.