methyl 3-(o-nitrophenyl)-2-oxo-1,2-dihydroquinoline-8-carboxylate | 289657-47-2

• 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: methyl 3-(o-nitrophenyl)-2-oxo-1,2-dihydroquinoline-8-carboxylate
• 英文别名: methyl 3-(2-nitrophenyl)-2-oxo-1H-quinoline-8-carboxylate
• CAS: 289657-47-2
• 化学式: C₁₇H₁₂N₂O₅
• 分子量: 324.293
• InChiKey: QUFWFLFALYBBSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3-(o-nitrophenyl)-2-oxo-1,2-dihydroquinoline-8-carboxylate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以100%的产率得到methyl 3-(o-aminophenyl)-2-oxo-1,2-dihydroquinoline-8-carboxylate
  参考文献：
  名称：

  摘要：

  The acid precursors of the title compounds were prepared from methyl 2-amino-3-formylbenzoate (3), by Friedlander synthesis with o-methoxy- and o-nitro-phenylacetic acids, phenylpyruvic acid and benzo[b]thiophen-2-one, respectively. Except for the last example, cyclization of an initial 3-arylquinoline derivative was then required to give the tetracycle. Growth inhibition properties of the carboxamides in a series of cancer cell lines were measured for comparison with previous data for an isomeric series. In all cases, the present set were found to be less active.

  DOI：

  10.1071/ch99166
• 作为产物：
  描述：

  2-硝基苯乙酸 、 2-氨基-3-羧酸甲酯苯甲醛 在 乙酸酐 、 三乙胺 作用下， 反应 48.0h， 以62%的产率得到methyl 3-(o-nitrophenyl)-2-oxo-1,2-dihydroquinoline-8-carboxylate
  参考文献：
  名称：

  摘要：

  The acid precursors of the title compounds were prepared from methyl 2-amino-3-formylbenzoate (3), by Friedlander synthesis with o-methoxy- and o-nitro-phenylacetic acids, phenylpyruvic acid and benzo[b]thiophen-2-one, respectively. Except for the last example, cyclization of an initial 3-arylquinoline derivative was then required to give the tetracycle. Growth inhibition properties of the carboxamides in a series of cancer cell lines were measured for comparison with previous data for an isomeric series. In all cases, the present set were found to be less active.

  DOI：

  10.1071/ch99166