2-溴-3-氟-5,7-二甲基喹啉-4-羧酸 | 834884-18-3

• 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
• 中文名称: 2-溴-3-氟-5,7-二甲基喹啉-4-羧酸
• 英文名称: 2-bromo-3-fluoro-5,7-dimethylquinoline-4-carboxylic acid
• CAS: 834884-18-3
• 化学式: C₁₂H₉BrFNO₂
• 分子量: 298.111
• InChiKey: BGLPIPQHETVTAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-溴-3-氟-5,7-二甲基喹啉-4-羧酸 在 正丁基锂 、 正丁基氯化镁 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 水 为溶剂， 反应 3.0h， 生成 3-fluoro-5,7-dimethyl-2-[(thiocarbamoyl)hydrazonomethyl]quinoline-4-carboxylic acid
  参考文献：
  名称：

  Metalation/functionalization sequences applied to 2-bromo-3-fluoroquinolines

  摘要：

  Mono- and disubstituted 2-bromo-3-fluoroquinotines 3 are readily accessible. They can be converted into the 3-fluoroquinoline-2-carboxylic acids 5 by consecutive halogen/metal permutation and into the 2-bromo-3-fluoroquinoline-4-carboxylic acids 6 by consecutive deprotonation and carboxylation. The latter compounds can be reduced to afford the 3-fluoroquinoline-4-carboxylic acids 7. The yields are excellent throughout. Rather than to introduce one functional group alternatively at the 2- or 4-position, one may also attach two different functional groups sequentially to both sites. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2004.10.053
• 作为产物：
  描述：

  3-fluoro-5,7-dimethylquinol-2(1H)-one 在 正丁基锂 、 二异丙胺 、 三溴氧磷 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.0h， 生成 2-溴-3-氟-5,7-二甲基喹啉-4-羧酸
  参考文献：
  名称：

  Metalation/functionalization sequences applied to 2-bromo-3-fluoroquinolines

  摘要：

  Mono- and disubstituted 2-bromo-3-fluoroquinotines 3 are readily accessible. They can be converted into the 3-fluoroquinoline-2-carboxylic acids 5 by consecutive halogen/metal permutation and into the 2-bromo-3-fluoroquinoline-4-carboxylic acids 6 by consecutive deprotonation and carboxylation. The latter compounds can be reduced to afford the 3-fluoroquinoline-4-carboxylic acids 7. The yields are excellent throughout. Rather than to introduce one functional group alternatively at the 2- or 4-position, one may also attach two different functional groups sequentially to both sites. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2004.10.053

文献信息

• Metalation/functionalization sequences applied to 2-bromo-3-fluoroquinolines
  作者：Levente Ondi、Jean-Noël Volle、Manfred Schlosser

  DOI：10.1016/j.tet.2004.10.053

  日期：2005.1

  Mono- and disubstituted 2-bromo-3-fluoroquinotines 3 are readily accessible. They can be converted into the 3-fluoroquinoline-2-carboxylic acids 5 by consecutive halogen/metal permutation and into the 2-bromo-3-fluoroquinoline-4-carboxylic acids 6 by consecutive deprotonation and carboxylation. The latter compounds can be reduced to afford the 3-fluoroquinoline-4-carboxylic acids 7. The yields are excellent throughout. Rather than to introduce one functional group alternatively at the 2- or 4-position, one may also attach two different functional groups sequentially to both sites. (C) 2004 Published by Elsevier Ltd.