dimethyl 6-fluoro-4-oxo-1,4-dihydroquinoline-2,3-dicarboxylate | 251986-63-7

• 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: dimethyl 6-fluoro-4-oxo-1,4-dihydroquinoline-2,3-dicarboxylate
• 英文别名: dimethyl 6-fluoro-4-oxo-1H-quinoline-2,3-dicarboxylate
• CAS: 251986-63-7
• 化学式: C₁₃H₁₀FNO₅
• 分子量: 279.225
• InChiKey: FKGJAEOJBOFTEY-UHFFFAOYSA-N

物化性质

• 沸点：
  390.5±42.0 °C(Predicted)
• 密度：
  1.413±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  dimethyl 6-fluoro-4-oxo-1,4-dihydroquinoline-2,3-dicarboxylate 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 1.0h， 以99%的产率得到6-fluoro-3-methoxycarbonyl-4-oxo-1H-quinoline-2-carboxylic acid
  参考文献：
  名称：

  A Synthesis of 4-Quinolone-3-carboxylic Acids via Pyrolysis of N-Aryldioxopyrrolines

  摘要：

  A synthesis of 4-quinolone-3-carboxylic acids (8) was achieved by pyrolysis of 4,5-dimethoxycarbonyl-1-aryl-1H-pyrrole-2,3-diones (3) followed by selective demethoxycarbonylation of the resulting 2,3-dimethoxycarbonyl-4-quinolones (4) in excellent overall yields.

  DOI：

  10.3987/com-99-8629
• 作为产物：
  描述：

  4,5-dimethoxycarbonyl-1-(4'-fluorophenyl)-1H-pyrrole-2,3-dione 以 二苯醚 为溶剂， 反应 0.5h， 以89%的产率得到dimethyl 6-fluoro-4-oxo-1,4-dihydroquinoline-2,3-dicarboxylate
  参考文献：
  名称：

  A Synthesis of 4-Quinolone-3-carboxylic Acids via Pyrolysis of N-Aryldioxopyrrolines

  摘要：

  A synthesis of 4-quinolone-3-carboxylic acids (8) was achieved by pyrolysis of 4,5-dimethoxycarbonyl-1-aryl-1H-pyrrole-2,3-diones (3) followed by selective demethoxycarbonylation of the resulting 2,3-dimethoxycarbonyl-4-quinolones (4) in excellent overall yields.

  DOI：

  10.3987/com-99-8629

文献信息

• Switchable Access to 3-Carboxylate-4-quinolones and 1-Vinyl-3-carboxylate-4-quinolones via Oxidative Cyclization of Isatins and Alkynes
  作者：Shi-Fen Jiang、Cheng Xu、Zhi-Wen Zhou、Qin Zhang、Xiao-Hui Wen、Feng-Cheng Jia、An-Xin Wu

  DOI：10.1021/acs.orglett.8b01645

  日期：2018.7.20

  An efficient transition-metal-free oxidative cyclization reaction using isatins and alkynes for the facile synthesis of structurally diverse 4-quinolones has been developed. Intriguingly, switchable access to substituted 3-carboxylate-4-quinolones and 1-vinyl-3-carboxylate-4-quinolones could be achieved by choosing a different base in the reaction. The obtained products could undergo further transformations, increasing the application potential of the method in organic synthesis.