ethyl 7-chloro-1-cyclopropyl-8-fluoro-6-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylate | 258345-91-4

• 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 7-chloro-1-cyclopropyl-8-fluoro-6-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylate
• CAS: 258345-91-4
• 化学式: C₁₅H₁₂ClFN₂O₅
• 分子量: 354.722
• InChiKey: CPGBMKHQGPAJIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.21
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  91.44
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ethyl 7-chloro-1-cyclopropyl-8-fluoro-6-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylate 在 镍 盐酸 、 氢气 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 20.0~90.0 ℃ 、207.72 kPa 条件下， 反应 45.0h， 生成 6-Amino-1-cyclopropyl-8-methoxy-7-(4-methyl-piperazin-1-yl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid
  参考文献：
  名称：

  Studies on 6-Aminoquinolones: synthesis and antibacterial evaluation of 6-amino-8-ethyl- and 6-amino-8-methoxyquinolones

  摘要：

  From our quantitative structure-activity relationship (QSAR) study on a large set of 6-aminoquinolones, which indicated that a group larger than methyl could be allocated at C-8 position, we have synthesized two new series of 6-aminoquinolones characterized by the presence of an ethyl or a methoxy group at C-8 position. The antibacterial evaluation shows that, while the 8-ethyl derivatives were devoid of any antibacterial activity, the introduction of methoxy group gave compounds with good antibacterial activity, especially against Gram-positive bacteria. A tentative explanation of the different behaviours among the 8-substituted analogues is given taking into account both the length and electronic properties of the C-8 groups. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00207-2
• 作为产物：
  描述：

  ethyl 2-(2,4-dichloro--3-fluoro-5-nitrobenzoyl)-3-(dimethylamino)acrylate 在 27 potassium carbonate 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 4.0h， 生成 ethyl 7-chloro-1-cyclopropyl-8-fluoro-6-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylate
  参考文献：
  名称：

  Studies on 6-Aminoquinolones: synthesis and antibacterial evaluation of 6-amino-8-ethyl- and 6-amino-8-methoxyquinolones

  摘要：

  From our quantitative structure-activity relationship (QSAR) study on a large set of 6-aminoquinolones, which indicated that a group larger than methyl could be allocated at C-8 position, we have synthesized two new series of 6-aminoquinolones characterized by the presence of an ethyl or a methoxy group at C-8 position. The antibacterial evaluation shows that, while the 8-ethyl derivatives were devoid of any antibacterial activity, the introduction of methoxy group gave compounds with good antibacterial activity, especially against Gram-positive bacteria. A tentative explanation of the different behaviours among the 8-substituted analogues is given taking into account both the length and electronic properties of the C-8 groups. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00207-2