1,3,4-triphenyl-1,3-dihydro-imidazol-2-one | 71624-07-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,3,4-triphenyl-1,3-dihydro-imidazol-2-one
• 英文别名: 1,3,4-Triphenyl-1,3-dihydro-imidazol-2-on；1,3,4-Triphenyl-1H-imidazole-2(3H)-one；1,3,4-triphenylimidazol-2-one
• CAS: 71624-07-2
• 化学式: C₂₁H₁₆N₂O
• 分子量: 312.371
• InChiKey: ODYFNEZFPKKHPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-Phenyl-2-phenylamino-ethanone oxime 在 对甲苯磺酸 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 3.75h， 生成 1,3,4-triphenyl-1,3-dihydro-imidazol-2-one
  参考文献：
  名称：

  Reactivity of bis(arylcarbamoyl)-N-arylphenacylamine oximes. Synthesis of 1,3-dihydroimidazol-2-ones and N-unsubstituted O-arylcarbamoylhydroxylamines

  摘要：

  N-Arylphenacylamine oximes I reacted with aryl isocyanates in refluxing benzene to give bis(arylcarbamoyl)-N-arylphenacylamine oximes 2 in good yields. Compounds 2 reacted with equimolar amount of TsOH.H2O in THF at room temperature to give imidazol-2-ones 5 and O-arylcarbamoylhydroxylammonium tosylates 6 in high yields. Compounds 2 were heated under vacuum to induce Beckmann fragmentation but the resulting products were 1,3,4-triaryl-1,3-dihydroimidazol-2-ones 5 instead of the expected 1,3-diazetidinones 4. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01046-1

文献信息

• McCombie; Scarborough, Journal of the Chemical Society, 1913, vol. 103, p. 60
  作者：McCombie、Scarborough

  DOI：——

  日期：——
• Reactivity of bis(arylcarbamoyl)-N-arylphenacylamine oximes. Synthesis of 1,3-dihydroimidazol-2-ones and N-unsubstituted O-arylcarbamoylhydroxylamines
  作者：Necdet Coşkun

  DOI：10.1016/s0040-4020(98)01046-1

  日期：1999.1

  N-Arylphenacylamine oximes I reacted with aryl isocyanates in refluxing benzene to give bis(arylcarbamoyl)-N-arylphenacylamine oximes 2 in good yields. Compounds 2 reacted with equimolar amount of TsOH.H2O in THF at room temperature to give imidazol-2-ones 5 and O-arylcarbamoylhydroxylammonium tosylates 6 in high yields. Compounds 2 were heated under vacuum to induce Beckmann fragmentation but the resulting products were 1,3,4-triaryl-1,3-dihydroimidazol-2-ones 5 instead of the expected 1,3-diazetidinones 4. (C) 1998 Elsevier Science Ltd. All rights reserved.