methyl 3-(o-methoxyphenyl)-2-oxo-1,2-dihydroquinoline-8-carboxylate | 289657-45-0

• 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-methoxyphenyl)-2-oxo-1,2-dihydroquinoline-8-carboxylate
• 英文别名: methyl 3-(2-methoxyphenyl)-2-oxo-1H-quinoline-8-carboxylate
• CAS: 289657-45-0
• 化学式: C₁₈H₁₅NO₄
• 分子量: 309.321
• InChiKey: GEHLPHZNFDRPDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 3-(o-methoxyphenyl)-2-oxo-1,2-dihydroquinoline-8-carboxylate 在 吡啶盐酸盐 作用下， 反应 1.5h， 以84%的产率得到benzofuro[2,3-b]quinoline-7-carboxylic acid
  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-甲氧基苯乙酸 、 2-氨基-3-羧酸甲酯苯甲醛 在 乙酸酐 、 三乙胺 作用下， 反应 30.0h， 以74%的产率得到methyl 3-(o-methoxyphenyl)-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