6,7-Difluoro-8-hydroxymethyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid | 144298-27-1

• 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: 6,7-Difluoro-8-hydroxymethyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
• 英文别名: 6,7-difluoro-8-(hydroxymethyl)-4-oxo-1H-quinoline-3-carboxylic acid
• CAS: 144298-27-1
• 化学式: C₁₁H₇F₂NO₄
• 分子量: 255.178
• InChiKey: XFDCFSQNDAJUKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  86.6
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2,3-Difluoro-6-(tert-butoxycarbamoyl)benzaldehyde 在 吡啶 、 盐酸 、 sodium hydroxide 、 sodium tetrahydroborate 作用下， 以 二苯醚 、 乙醚 、 乙醇 为溶剂， 反应 7.17h， 生成 6,7-Difluoro-8-hydroxymethyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
  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.