diethyl 4-p-methoxyphenylaminoquinoline-3-phosphonate | 228249-10-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: diethyl 4-p-methoxyphenylaminoquinoline-3-phosphonate
• 英文别名: 3-diethoxyphosphoryl-N-(4-methoxyphenyl)quinolin-4-amine
• CAS: 228249-10-3
• 化学式: C₂₀H₂₃N₂O₄P
• 分子量: 386.387
• InChiKey: TVHXRFPMQUYKHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  69.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl 4-p-methoxyphenylaminoquinoline-3-phosphonate 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.5h， 以91%的产率得到diethyl 4-aminoquinoline-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：

  Diethyl-(2-anilinovinyl)-phosphonat 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 diethyl 4-p-methoxyphenylaminoquinoline-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

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.