ethyl 2,4,5-trifluoro-β-oxo-3-(trifluoromethyl)benzenepropanoate | 118829-15-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2,4,5-trifluoro-β-oxo-3-(trifluoromethyl)benzenepropanoate
• 英文别名: Ethyl 3-oxo-3-[2,4,5-trifluoro-3-(trifluoromethyl)phenyl]propanoate
• CAS: 118829-15-5
• 化学式: C₁₂H₈F₆O₃
• 分子量: 314.184
• InChiKey: FNEOEJNSNFRCFJ-UHFFFAOYSA-N

物化性质

• 沸点：
  284.0±35.0 °C(Predicted)
• 密度：
  1.427±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  ethyl 2,4,5-trifluoro-β-oxo-3-(trifluoromethyl)benzenepropanoate 在 盐酸 、 乙酸酐 、 三乙胺 作用下， 以 四氢呋喃 、 二甲基亚砜 、 乙腈 为溶剂， 反应 173.0h， 生成 1-环丙基-6-氟-4-氧代-7-哌嗪-1-基-8-(三氟甲基)喹啉-3-羧酸
  参考文献：
  名称：

  New 8-(trifluoromethyl)-substituted quinolones. The benefits of the 8-fluoro group with reduced phototoxic risk

  摘要：

  A series of 8-(trifluoromethyl)-substituted quinolones has been prepared and evaluated for in vitro and in vivo antibacterial activity, and phototolerance in a mouse phototolerance assay. These analogues were compared to the corresponding series of 6,8-difluoro- and 6-fluoro-8H-quinolones (ciprofloxacin type). Although their in vitro antibacterial activities are less than the 6,8-difluoro analogues, the 8-(trifluoromethyl)quinolones are generally equivalent to their 8H analogues. In vivo, they are comparable to the 6,8-difluoro series and show up to 10-fold improvement in efficacy when compared to their ciprofloxacin counterparts vs Streptococcus pyogenes and Streptococcus pneumonia. In the phototolerance model, the 8-(trifluoromethyl)quinolones are comparable to the 8H-quinolones. Both of these series display much higher no effect doses (greater tolerance) than the corresponding 6,8-difluoroquinolones.

  DOI：

  10.1021/jm00080a023
• 作为产物：
  描述：

  2,-三氟-(氟甲基)苯甲酸 在 草酰氯 、 异丙基氯化镁 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.33h， 生成 ethyl 2,4,5-trifluoro-β-oxo-3-(trifluoromethyl)benzenepropanoate
  参考文献：
  名称：

  New 8-(trifluoromethyl)-substituted quinolones. The benefits of the 8-fluoro group with reduced phototoxic risk

  摘要：

  A series of 8-(trifluoromethyl)-substituted quinolones has been prepared and evaluated for in vitro and in vivo antibacterial activity, and phototolerance in a mouse phototolerance assay. These analogues were compared to the corresponding series of 6,8-difluoro- and 6-fluoro-8H-quinolones (ciprofloxacin type). Although their in vitro antibacterial activities are less than the 6,8-difluoro analogues, the 8-(trifluoromethyl)quinolones are generally equivalent to their 8H analogues. In vivo, they are comparable to the 6,8-difluoro series and show up to 10-fold improvement in efficacy when compared to their ciprofloxacin counterparts vs Streptococcus pyogenes and Streptococcus pneumonia. In the phototolerance model, the 8-(trifluoromethyl)quinolones are comparable to the 8H-quinolones. Both of these series display much higher no effect doses (greater tolerance) than the corresponding 6,8-difluoroquinolones.

  DOI：

  10.1021/jm00080a023

文献信息

• 8-trifluoromethyl quinolones as antibacterial agents
  申请人：Warner-Lambert Company

  公开号：US04780468A1

  公开（公告）日：1988-10-25

  A novel series of quinolone carboxylic acids for use as antibacterial agents are described. Methods for making the compounds, methods of using the compounds and compositions containing them are also described. Certain novel intermediates are also described.

  描述了一系列新的喹诺酮羧酸，用作抗菌剂。还描述了制备化合物的方法，使用化合物的方法以及含有它们的组合物。还描述了某些新的中间体。
• Quinolones as antibacterial agents
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0302525A2

  公开（公告）日：1989-02-08

  A novel series of quinolone carboxylic acid derivatives of the formula for use as antibacterial agents are described. Methods for making the compounds, methods of using the compounds and compositions containing them are also described. Certain novel intermediates are also described.

  本研究描述了一系列新型喹诺酮羧酸衍生物，其式为 描述了用作抗菌剂的一系列新型喹诺酮羧酸衍生物。还描述了制造这些化合物的方法、使用这些化合物的方法以及含有这些化合物的组合物。还介绍了某些新型中间体。
• BRIDGES, ALEXANDER J.;DOMAGALA, JOHN M.
  作者：BRIDGES, ALEXANDER J.、DOMAGALA, JOHN M.

  DOI：——

  日期：——
• US4780468A
  申请人：——

  公开号：US4780468A

  公开（公告）日：1988-10-25
• US4803205A
  申请人：——

  公开号：US4803205A

  公开（公告）日：1989-02-07