5-methoxy-7-fluoroquinoline

• 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: 5-methoxy-7-fluoroquinoline
• 英文别名: 7-Fluoro-5-methoxyquinoline；7-fluoro-5-methoxyquinoline
• 化学式: C₁₀H₈FNO
• 分子量: 177.178
• InChiKey: ZMKZIATVLZFCOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  甲醇 、 5, 7-二氟喹啉 在 sodium 作用下， 以 氨 为溶剂， 生成 5-fluoro-7-methoxyquinoline 、 5-methoxy-7-fluoroquinoline
  参考文献：
  名称：

  Regioselectivity and relative substrate activity of difluoroquinolines containing fluorine atoms in benzene ring in reaction with sodium methoxide

  摘要：

  Methoxydefluorination of 5,7-, 6,7-, 6,8-, and 5,8-difluoroquinoline (1-4) by the action of sodium methoxide has been studied in liquid ammonia and Me,SO. The regioselectivity of methoxydefluorination of I and 2 in the temperature interval 218-240 K in liquid ammonia and 1 and 4 in the interval 298-378 K in Me2SO as well as the activity correlation of individual reaction centers in different substrates have been established as enthalpically controlled. The overall pattern of relative reactivity is consistent with the ab initio (RHF/6-31G*) calculated relative stabilities and electronic structures of the sigma-complexes formed by the substrates with the hydroxide anion as a model nucleophile. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2005.08.010

文献信息

• Regioselectivity and relative substrate activity of difluoroquinolines containing fluorine atoms in benzene ring in reaction with sodium methoxide
  作者：Larisa V. Politanskaya、Lyudmila A. Malysheva、Irina V. Beregovaya、Irina Yu. Bagryanskaya、Yuri V. Gatilov、Evgenij V. Malykhin、Vitalij D. Shteingarts

  DOI：10.1016/j.jfluchem.2005.08.010

  日期：2005.12

  Methoxydefluorination of 5,7-, 6,7-, 6,8-, and 5,8-difluoroquinoline (1-4) by the action of sodium methoxide has been studied in liquid ammonia and Me,SO. The regioselectivity of methoxydefluorination of I and 2 in the temperature interval 218-240 K in liquid ammonia and 1 and 4 in the interval 298-378 K in Me2SO as well as the activity correlation of individual reaction centers in different substrates have been established as enthalpically controlled. The overall pattern of relative reactivity is consistent with the ab initio (RHF/6-31G*) calculated relative stabilities and electronic structures of the sigma-complexes formed by the substrates with the hydroxide anion as a model nucleophile. (c) 2005 Elsevier B.V. All rights reserved.