ethyl 3-(acetylamino)-2-oxo-1,2-dihydroquinoline-4-carboxylate | 1325711-20-3

• 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: ethyl 3-(acetylamino)-2-oxo-1,2-dihydroquinoline-4-carboxylate
• 英文别名: ethyl 3-acetamido-2-oxo-1H-quinoline-4-carboxylate
• CAS: 1325711-20-3
• 化学式: C₁₄H₁₄N₂O₄
• 分子量: 274.276
• InChiKey: MNELWXMLSCYUEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  84.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  靛红 在 四氯化锡 、 二乙胺 作用下， 以 乙醇 为溶剂， 反应 72.0h， 生成 ethyl 3-(acetylamino)-2-oxo-1,2-dihydroquinoline-4-carboxylate 、 ethyl 3-(2-aminophenyl)-2-propynoate
  参考文献：
  名称：

  Exploring the Synthetic Versatility of the Lewis Acid Induced Decomposition Reaction of α-Diazo-β-hydroxy Esters. The Case of Ethyl Diazo(3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)acetate

  摘要：

  Ethyl diazo(3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)acetate was prepared by aldol-type condensation of ethyl diazoacetate with isatin. A systematic and mechanistic study on the Lewis acid induced decomposition reaction of this valuable diazo precursor was carried out with the aim to gain new insights into the mechanistic aspects of the reaction as well as to further understand the factors and experimental conditions which affect the relative product distribution. The reaction, which may proceed via cationic and noncationic mechanisms, was found to be significantly influenced by the reaction environment determined by the characteristics of the Lewis acid employed, by the ability of the Lewis acid to form a complex with the alcohol functionality of the alpha-diazo-beta-hydroxy ester, and by the polarity and nucleophilicity of the solvent used.

  DOI：

  10.1021/jo201205u