E-2-(N-phenylamino)ethenyl diphenylphosphine oxide | 228248-94-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: E-2-(N-phenylamino)ethenyl diphenylphosphine oxide
• 英文别名: N-[(E)-2-diphenylphosphorylethenyl]aniline
• CAS: 228248-94-0
• 化学式: C₂₀H₁₈NOP
• 分子量: 319.343
• InChiKey: UUGZLCBNIVVOKW-WUKNDPDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  E-2-(N-phenylamino)ethenyl diphenylphosphine oxide 在 正丁基锂 、 六氯乙烷 、 三乙胺 、 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 26.0h， 生成 4-propylaminoquinoline-3-diphenylphosphine oxide
  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：

  (diphenylphosphinyl)acetaldehyde 、 苯胺 在 magnesium sulfate 作用下， 以 四氢呋喃 为溶剂， 以92%的产率得到E-2-(N-phenylamino)ethenyl diphenylphosphine oxide
  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

• Reaction of 1,3,5-Triazinanes with Phosphoryl Diazomethanes: Access to 5-Phosphoryl-1,2,3,4-tetrahydropyrimidines
  作者：Wenlai Xie、Chengzhuo Wang、Jiaxi Xu

  DOI：10.1021/acs.orglett.4c00881

  日期：2024.4.26

  s is achieved efficiently through the microwave-assisted reaction with phosphoryl diazomethanes. Both trialkyl and triaryl 1,3,5-triazinanes were converted by diazomethyldiarylphosphine oxides, dialkyl diazomethylphosphonates, and alkyl diazomethyl(aryl)phosphinates and functionalized simultaneously in good to excellent yields. The reaction is a sequence of 1,3,5-triazinane fragmentation, tandem nucleophilic

  通过与磷酰重氮甲烷的微波辅助反应，可以有效地将 1,3,5-三嗪转化为 5-磷酰基-1,2,3,4-四氢嘧啶。三烷基和三芳基1,3,5-三嗪烷均可通过重氮甲基二芳基氧化膦、重氮甲基膦酸二烷基酯和重氮甲基（芳基）次膦酸烷基酯转化并同时官能化，收率良好至优异。该反应是一系列 1,3,5-三嗪烷断裂、生成的福尔马亚胺和磷酰重氮甲烷的串联亲核加成，以及最终的N , N-缩醛化。
• 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.