3-diethoxyphosphoryl-6-methyl-2-phenyl-1H-pyridin-4-one | 205651-77-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-diethoxyphosphoryl-6-methyl-2-phenyl-1H-pyridin-4-one
• CAS: 205651-77-0
• 化学式: C₁₆H₂₀NO₄P
• 分子量: 321.313
• InChiKey: POPSRCHETMYDDR-UHFFFAOYSA-N

物化性质

• 沸点：
  456.3±45.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-diethoxyphosphoryl-6-methyl-2-phenyl-1H-pyridin-4-one 在 三氯氧磷 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 以72%的产率得到(4-Chloro-6-methyl-2-phenyl-pyridin-3-yl)-phosphonic acid diethyl ester
  参考文献：
  名称：

  An Efficient Synthesis of 3-Phosphorylated 4(1H)-Pyridones and 4-Chloropyridines fromb-Enaminophosphonates

  摘要：

  An easy and efficient synthesis of 4(1H)-pyridones (1) substituted with a phosphate group in the 3-position is described. The key step is an addition of beta-enaminophosphonates (2) to acylketene (3) generated either from diketene (4) or from the "diketene-acetone adduct", 2,2,6-trimethyl-4H-1,3-dioxin-4-one (5), Subsequent treatment of 4(1H)-pyridones with phosphorus oxychloride in the presence of dimethylformamide afforded the substituted 4-chloropyridine (6).

  DOI：

  10.3987/com-97-s(n)70
• 作为产物：
  描述：

  2,2,6-三甲基-4H-1,3-二英-4-酮 、 diethyl 2-amino-2-phenylvinylphosphonate 以 neat (no solvent) 为溶剂， 反应 12.0h， 以92%的产率得到3-diethoxyphosphoryl-6-methyl-2-phenyl-1H-pyridin-4-one
  参考文献：
  名称：

  An Efficient Synthesis of 3-Phosphorylated 4(1H)-Pyridones and 4-Chloropyridines fromb-Enaminophosphonates

  摘要：

  An easy and efficient synthesis of 4(1H)-pyridones (1) substituted with a phosphate group in the 3-position is described. The key step is an addition of beta-enaminophosphonates (2) to acylketene (3) generated either from diketene (4) or from the "diketene-acetone adduct", 2,2,6-trimethyl-4H-1,3-dioxin-4-one (5), Subsequent treatment of 4(1H)-pyridones with phosphorus oxychloride in the presence of dimethylformamide afforded the substituted 4-chloropyridine (6).

  DOI：

  10.3987/com-97-s(n)70