Ethyl 6,7-difluoro-1,4-dihydro-8-methylthio-4-oxoquinoline-3-carboxylate | 144298-20-4

• 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 6,7-difluoro-1,4-dihydro-8-methylthio-4-oxoquinoline-3-carboxylate
• 英文别名: Jptwfbfpwonysz-uhfffaoysa-；ethyl 6,7-difluoro-8-methylsulfanyl-4-oxo-1H-quinoline-3-carboxylate
• CAS: 144298-20-4
• 化学式: C₁₃H₁₁F₂NO₃S
• 分子量: 299.298
• InChiKey: JPTWFBFPWONYSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Ethyl 6,7-difluoro-1,4-dihydro-8-methylthio-4-oxoquinoline-3-carboxylate 在 盐酸 、 溶剂黄146 作用下， 以 二甲基亚砜 为溶剂， 反应 31.0h， 生成 6-Fluoro-7-(4-methyl-1-piperazinyl)-1,4-dihydro-8-methylthio-4-oxoquinoline-3-carboxylic acid hydrochloride
  参考文献：
  名称：

  A practical route to C-8 substituted fluoroquinolones

  摘要：

  The ortho metalation of N-(tert-butoxycarbonyl)-3,4-difluoroaniline, with t-BuLi at -78-degrees-C in THF occured regioselectively at C-2 position. The resulting lithiated species reacted with a variety of electrophiles to give 2-substituted-3,4-difluoroanilines in good yields after hydrolysis. These compounds have been readily transformed into C-8 substituted fluoroquinolones. The nucleophilic substitution at C-7 by piperazines and the alkylation at N-1 on these quinolones have also been performed.

  DOI：

  10.1016/s0040-4020(01)88273-9
• 作为产物：
  描述：

  3,4-Difluoro-2-methylthioaniline 以 二苯醚 为溶剂， 反应 12.5h， 生成 Ethyl 6,7-difluoro-1,4-dihydro-8-methylthio-4-oxoquinoline-3-carboxylate
  参考文献：
  名称：

  A practical route to C-8 substituted fluoroquinolones

  摘要：

  The ortho metalation of N-(tert-butoxycarbonyl)-3,4-difluoroaniline, with t-BuLi at -78-degrees-C in THF occured regioselectively at C-2 position. The resulting lithiated species reacted with a variety of electrophiles to give 2-substituted-3,4-difluoroanilines in good yields after hydrolysis. These compounds have been readily transformed into C-8 substituted fluoroquinolones. The nucleophilic substitution at C-7 by piperazines and the alkylation at N-1 on these quinolones have also been performed.

  DOI：

  10.1016/s0040-4020(01)88273-9

文献信息

• A practical route to C-8 substituted fluoroquinolones
  作者：Juan C. Carretero、José L. García Ruano、Mercedes Vicioso

  DOI：10.1016/s0040-4020(01)88273-9

  日期：1992.1

  The ortho metalation of N-(tert-butoxycarbonyl)-3,4-difluoroaniline, with t-BuLi at -78-degrees-C in THF occured regioselectively at C-2 position. The resulting lithiated species reacted with a variety of electrophiles to give 2-substituted-3,4-difluoroanilines in good yields after hydrolysis. These compounds have been readily transformed into C-8 substituted fluoroquinolones. The nucleophilic substitution at C-7 by piperazines and the alkylation at N-1 on these quinolones have also been performed.