Diethyl (3,4-difluoro-2-methylthioanilinyl)methylidenemalonate | 144298-17-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: Diethyl (3,4-difluoro-2-methylthioanilinyl)methylidenemalonate
• 英文别名: Diethyl 2-[(3,4-difluoro-2-methylsulfanylanilino)methylidene]propanedioate
• CAS: 144298-17-9
• 化学式: C₁₅H₁₇F₂NO₄S
• 分子量: 345.367
• InChiKey: XMQAHUYFEPVDNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Diethyl (3,4-difluoro-2-methylthioanilinyl)methylidenemalonate 以 二苯醚 为溶剂， 反应 10.0h， 以58%的产率得到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
• 作为产物：
  描述：

  3,4-Difluoro-2-methylthio-N-(tert-butoxycarbonyl)aniline 在 盐酸 作用下， 以 乙醚 为溶剂， 反应 19.5h， 生成 Diethyl (3,4-difluoro-2-methylthioanilinyl)methylidenemalonate
  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.