ethyl 2,3a-diphenyl-5-(p-tolyl)-3a,4,5,6-tetrahydroimidazo[1,5-b]isoxazole-3-carboxylate | 592543-07-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: ethyl 2,3a-diphenyl-5-(p-tolyl)-3a,4,5,6-tetrahydroimidazo[1,5-b]isoxazole-3-carboxylate
• 英文别名: Ethyl 5-(4-methylphenyl)-2,3a-diphenyl-4,6-dihydroimidazo[1,5-b][1,2]oxazole-3-carboxylate
• CAS: 592543-07-2
• 化学式: C₂₇H₂₆N₂O₃
• 分子量: 426.515
• InChiKey: KWTSXXCAHSTNET-UHFFFAOYSA-N

物化性质

• 沸点：
  584.3±60.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  42
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2,3a-diphenyl-5-(p-tolyl)-3a,4,5,6-tetrahydroimidazo[1,5-b]isoxazole-3-carboxylate 反应 0.25h， 以95%的产率得到4-phenyl-1-(p-tolyl)-1H-imidazole
  参考文献：
  名称：

  Synthesis of 4‐Oxo‐3a,4,5,6‐tetrahydroimidazo[1,5‐b]isoxazole‐3‐carboxylic Acid Esters

  摘要：

  3-Imidazoline 3-oxides react regioselectively with 3-phenylpropanoic acid alkyl esters to give the corresponding 2-phenyl-3a,4,5,6-tetrahydroimidazol 1,5-b]isoxazole-3-carboxylic acid alkyl esters. This adducts convert to imidazole and the corresponding. alkyl 3-oxo-3-phenylpropanoic acid esters when treated with alkoxides or heated under vacuum. Attempts to oxidise the carbon-carbon double bond using KMnO4-FeSO4 led to the formation of heretofore unknown 4-oxo-3a,4,5,6-tetrahydroimidazo[1,5-b]isoxazoles.

  DOI：

  10.1081/scc-120030749
• 作为产物：
  描述：

  4-phenyl-1-(p-tolyl)-2,5-dihydro-1H-imidazole 3-oxide 、 苯丙炔酸乙酯 以 甲苯 为溶剂， 反应 24.0h， 以90%的产率得到ethyl 2,3a-diphenyl-5-(p-tolyl)-3a,4,5,6-tetrahydroimidazo[1,5-b]isoxazole-3-carboxylate
  参考文献：
  名称：

  Synthesis of 4‐Oxo‐3a,4,5,6‐tetrahydroimidazo[1,5‐b]isoxazole‐3‐carboxylic Acid Esters

  摘要：

  3-Imidazoline 3-oxides react regioselectively with 3-phenylpropanoic acid alkyl esters to give the corresponding 2-phenyl-3a,4,5,6-tetrahydroimidazol 1,5-b]isoxazole-3-carboxylic acid alkyl esters. This adducts convert to imidazole and the corresponding. alkyl 3-oxo-3-phenylpropanoic acid esters when treated with alkoxides or heated under vacuum. Attempts to oxidise the carbon-carbon double bond using KMnO4-FeSO4 led to the formation of heretofore unknown 4-oxo-3a,4,5,6-tetrahydroimidazo[1,5-b]isoxazoles.

  DOI：

  10.1081/scc-120030749

文献信息

• Synthesis of 4‐Oxo‐3a,4,5,6‐tetrahydroimidazo[1,5‐<i>b</i>]isoxazole‐3‐carboxylic Acid Esters
  作者：Necdet Coşkun、Bilal Yılmaz

  DOI：10.1081/scc-120030749

  日期：2004.12.31

  3-Imidazoline 3-oxides react regioselectively with 3-phenylpropanoic acid alkyl esters to give the corresponding 2-phenyl-3a,4,5,6-tetrahydroimidazol 1,5-b]isoxazole-3-carboxylic acid alkyl esters. This adducts convert to imidazole and the corresponding. alkyl 3-oxo-3-phenylpropanoic acid esters when treated with alkoxides or heated under vacuum. Attempts to oxidise the carbon-carbon double bond using KMnO4-FeSO4 led to the formation of heretofore unknown 4-oxo-3a,4,5,6-tetrahydroimidazo[1,5-b]isoxazoles.