E-2-(diethylphosphinoyl)-3-phenyl-3-(N-phenylamino)-N-propylprop-2-enamide

• 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: E-2-(diethylphosphinoyl)-3-phenyl-3-(N-phenylamino)-N-propylprop-2-enamide
• 英文别名: (E)-3-anilino-2-diethoxyphosphoryl-3-phenyl-N-propylprop-2-enamide
• 化学式: C₂₂H₂₉N₂O₄P
• 分子量: 416.457
• InChiKey: BBTRYUIAVJBOJV-QZQOTICOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  E-2-(diethylphosphinoyl)-3-phenyl-3-(N-phenylamino)-N-propylprop-2-enamide 在 六氯乙烷 、 三乙胺 、 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 20.0h， 以64%的产率得到diethyl 2-phenyl-4-propylaminoquinoline-3-phosphonate
  参考文献：
  名称：

  A simple synthesis of 3-phosphonyl-4-aminoquinolines from β-enaminophosphonates

  摘要：

  An easy and efficient synthesis of 4-aminoquinolines substituted with a phosphorylated group or a phosphine oxide group in the 3-position is described. The key step is a regioselective addition of lithiated beta-enamino phosphonates to isocyanates to give functionalized amides. Subsequent cyclization of these compounds with triphenylphosphine and hexachloroethane in the presence of triethylamine afforded substituted 4-aminoquinolines. The deprotection of N-PMP substituted 4-amino-quinolines with CAN in acetonitrile gave primary 4-aminoquinolines. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00257-4
• 作为产物：
  描述：

  异氰酸丙酯 、 (2-氧代-2-苯乙基)膦酸二乙酯 、 苯胺 生成 E-2-(diethylphosphinoyl)-3-phenyl-3-(N-phenylamino)-N-propylprop-2-enamide
  参考文献：
  名称：

  A simple synthesis of 3-phosphonyl-4-aminoquinolines from β-enaminophosphonates

  摘要：

  An easy and efficient synthesis of 4-aminoquinolines substituted with a phosphorylated group or a phosphine oxide group in the 3-position is described. The key step is a regioselective addition of lithiated beta-enamino phosphonates to isocyanates to give functionalized amides. Subsequent cyclization of these compounds with triphenylphosphine and hexachloroethane in the presence of triethylamine afforded substituted 4-aminoquinolines. The deprotection of N-PMP substituted 4-amino-quinolines with CAN in acetonitrile gave primary 4-aminoquinolines. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00257-4

文献信息

• A simple synthesis of 3-phosphonyl-4-aminoquinolines from β-enaminophosphonates
  作者：Francisco Palacios、Ana M. Ochoa de Retana、Julen Oyarzabal

  DOI：10.1016/s0040-4020(99)00257-4

  日期：1999.4

  An easy and efficient synthesis of 4-aminoquinolines substituted with a phosphorylated group or a phosphine oxide group in the 3-position is described. The key step is a regioselective addition of lithiated beta-enamino phosphonates to isocyanates to give functionalized amides. Subsequent cyclization of these compounds with triphenylphosphine and hexachloroethane in the presence of triethylamine afforded substituted 4-aminoquinolines. The deprotection of N-PMP substituted 4-amino-quinolines with CAN in acetonitrile gave primary 4-aminoquinolines. (C) 1999 Elsevier Science Ltd. All rights reserved.