diethyl (4-oxo-1,4-dihydroquinolin-3-yl)phosphonate | 1346446-74-9

• 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-oxo-1,4-dihydroquinolin-3-yl)phosphonate
• CAS: 1346446-74-9；49667-05-2
• 化学式: C₁₃H₁₆NO₄P
• 分子量: 281.248
• InChiKey: LIVCSXCXXAVHOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.83
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  68.65
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  以 diphenyl ether-biphenyl eutectic 为溶剂， 反应 0.25h， 以29%的产率得到diethyl (4-oxo-1,4-dihydroquinolin-3-yl)phosphonate
  参考文献：
  名称：

  Efficient synthesis of phosphorylated ortho-fused azaheterocycles

  摘要：

  A simple and efficient two-step synthesis of various ortho-fused azaheterocycles, containing phosphorylated pyrimidinones as a parent component, was accomplished by the reaction of 2-diethoxyphosphoryl-3-methoxyacrylate with heteroaromatic amines followed by intramolecular N-acylation of the obtained substitution products. Optimization studies performed for the N-acylation reaction revealed that heating the addition products in Dowtherm A at 250 C gave the best results. The same conditions applied in the intramolecular cyclization of ethyl 2-diethoxyphosphoryl-3-aminophenylacrylate gave expected product of the electrophilic aromatic substitution, but in low yield. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.139