ethyl 2-benzoyl-3-(2-hydroxy-8-methylimidazo[1,2-a]pyridin-3-yl)-3-(methylthio)acrylate | 1210317-29-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: ethyl 2-benzoyl-3-(2-hydroxy-8-methylimidazo[1,2-a]pyridin-3-yl)-3-(methylthio)acrylate
• CAS: 1210317-29-5
• 化学式: C₂₁H₂₀N₂O₄S
• 分子量: 396.467
• InChiKey: KFRNOVUPQBGVTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.87
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  80.9
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-benzoyl-3-(2-hydroxy-8-methylimidazo[1,2-a]pyridin-3-yl)-3-(methylthio)acrylate 100.0 ℃ 、399.97 Pa 条件下， 反应 0.25h， 以66%的产率得到3-benzoyl-9-methyl-4-(methylthio)-2H-pyrano[2',3':4,5]imidazo[1,2-a]pyridin-2-one
  参考文献：
  名称：

  A New Approach to Imidazo[1,2-a]pyridine Derivatives and Their Application to the Syntheses of Novel 2H-Pyrano[2’,3’:4,5]imidazo[1,2-a]pyridin-2-one Derivatives

  摘要：

  3-[Bis(methylthio)methylene]-2(3H)-imidazo[1,2-a]pyridinones were prepared from the S-alkylation of pyridinium 1-[1-carbamoyl-1-[(methylthio) thiocarbonyl]]methylides with methyl iodide followed by the alkaline treatment of the resulting pyridinium salts. The reactions of these 3-methylene-2(3H)-imidazo[1,2-a]pyridinones with some ethyl cyano- or acyl-substituted acetates in the presence of a base did not afford the initially expected 2H-pyrano[2',3':4,5]imidazo[1,2-a]pyridine-2-one derivatives, but, instead of them, provided ethyl 3[2-hydroxyimidazo[1,2-a]pyridin-3-yl]acrylates. The thermolyses of these acrylates without any solvent under reduced pressure gave the corresponding 2H-pyrano[2',3':4,5]imidazo[1,2-a]pyridine-2-one derivatives.

  DOI：

  10.3987/com-09-s(s)41
• 作为产物：
  描述：

  (bis(methylthio))methylidene-8-methylimidazo[1,2-a]pyridin-2(3H)-one 、 苯甲酰乙酸乙酯 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 反应 17.0h， 以98%的产率得到ethyl 2-benzoyl-3-(2-hydroxy-8-methylimidazo[1,2-a]pyridin-3-yl)-3-(methylthio)acrylate
  参考文献：
  名称：

  A New Approach to Imidazo[1,2-a]pyridine Derivatives and Their Application to the Syntheses of Novel 2H-Pyrano[2’,3’:4,5]imidazo[1,2-a]pyridin-2-one Derivatives

  摘要：

  3-[Bis(methylthio)methylene]-2(3H)-imidazo[1,2-a]pyridinones were prepared from the S-alkylation of pyridinium 1-[1-carbamoyl-1-[(methylthio) thiocarbonyl]]methylides with methyl iodide followed by the alkaline treatment of the resulting pyridinium salts. The reactions of these 3-methylene-2(3H)-imidazo[1,2-a]pyridinones with some ethyl cyano- or acyl-substituted acetates in the presence of a base did not afford the initially expected 2H-pyrano[2',3':4,5]imidazo[1,2-a]pyridine-2-one derivatives, but, instead of them, provided ethyl 3[2-hydroxyimidazo[1,2-a]pyridin-3-yl]acrylates. The thermolyses of these acrylates without any solvent under reduced pressure gave the corresponding 2H-pyrano[2',3':4,5]imidazo[1,2-a]pyridine-2-one derivatives.

  DOI：

  10.3987/com-09-s(s)41