2,4,6-trifluoro-N-(quinolin-8-yl)benzamide | 1443144-29-3

• 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
• 英文名称: 2,4,6-trifluoro-N-(quinolin-8-yl)benzamide
• 英文别名: 2,4,6-trifluoro-N-quinolin-8-ylbenzamide
• CAS: 1443144-29-3
• 化学式: C₁₆H₉F₃N₂O
• 分子量: 302.255
• InChiKey: YFVCRDXQNCLMOA-UHFFFAOYSA-N

物化性质

• 沸点：
  367.0±42.0 °C(Predicted)
• 密度：
  1.451±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,4,6-trifluoro-N-(quinolin-8-yl)benzamide 在 sodium hydroxide 、 盐酸 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 24.0h， 以82%的产率得到2,4,6-三氟苯甲酸
  参考文献：
  名称：

  Copper-Catalyzed, Directing Group-Assisted Fluorination of Arene and Heteroarene C–H Bonds

  摘要：

  We have developed a method for direct, copper-catalyzed, auxiliary-assisted fluorination of beta-sp(2) C-H bonds of benzoic acid derivatives and gamma-sp(2) C-H bonds of alpha,alpha-disubstituted benzylamine derivatives. The reaction employs a CuI catalyst, a AgF fluoride source, and DMF, pyridine, or DMPU solvent at moderately elevated temperatures. Selective mono- or difluorination can be achieved by simply changing reaction conditions. The method shows excellent functional group tolerance and provides a straightforward way for the preparation of ortho-fluorinated benzoic acids.

  DOI：

  10.1021/ja4047125
• 作为产物：
  描述：

  4-fluoro-N-(quinolin-8-yl)benzamide 在 吡啶 、 copper(l) iodide 、 silver fluoride 、 N-甲基吗啉氧化物 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以61%的产率得到2,4,6-trifluoro-N-(quinolin-8-yl)benzamide
  参考文献：
  名称：

  Copper-Catalyzed, Directing Group-Assisted Fluorination of Arene and Heteroarene C–H Bonds

  摘要：

  We have developed a method for direct, copper-catalyzed, auxiliary-assisted fluorination of beta-sp(2) C-H bonds of benzoic acid derivatives and gamma-sp(2) C-H bonds of alpha,alpha-disubstituted benzylamine derivatives. The reaction employs a CuI catalyst, a AgF fluoride source, and DMF, pyridine, or DMPU solvent at moderately elevated temperatures. Selective mono- or difluorination can be achieved by simply changing reaction conditions. The method shows excellent functional group tolerance and provides a straightforward way for the preparation of ortho-fluorinated benzoic acids.

  DOI：

  10.1021/ja4047125

文献信息

• Copper-Catalyzed, Directing Group-Assisted Fluorination of Arene and Heteroarene C–H Bonds
  作者：Thanh Truong、Kristine Klimovica、Olafs Daugulis

  DOI：10.1021/ja4047125

  日期：2013.6.26

  We have developed a method for direct, copper-catalyzed, auxiliary-assisted fluorination of beta-sp(2) C-H bonds of benzoic acid derivatives and gamma-sp(2) C-H bonds of alpha,alpha-disubstituted benzylamine derivatives. The reaction employs a CuI catalyst, a AgF fluoride source, and DMF, pyridine, or DMPU solvent at moderately elevated temperatures. Selective mono- or difluorination can be achieved by simply changing reaction conditions. The method shows excellent functional group tolerance and provides a straightforward way for the preparation of ortho-fluorinated benzoic acids.