2-fluoro-4-nitro-N-(quinolin-8-yl)benzamide | 1443144-21-5

• 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-fluoro-4-nitro-N-(quinolin-8-yl)benzamide
• 英文别名: 2-fluoro-N-(quinolin-8-yl)-4-nitrobenzamide；2-fluoro-4-nitro-N-quinolin-8-ylbenzamide
• CAS: 1443144-21-5
• 化学式: C₁₆H₁₀FN₃O₃
• 分子量: 311.272
• InChiKey: DBVWSSIDNGHIPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 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：
  87.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-nitro-N-(quinolin-8-yl)benzamide 在 吡啶 、 copper(l) iodide 、 silver fluoride 、 N-甲基吗啉氧化物 作用下， 反应 2.13h， 以60%的产率得到2-fluoro-4-nitro-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‐Mediated Aminoquinoline‐Directed Radiofluorination of Aromatic C−H Bonds with K ¹⁸ F
  作者：So Jeong Lee、Katarina J. Makaravage、Allen F. Brooks、Peter J. H. Scott、Melanie S. Sanford

  DOI：10.1002/anie.201812701

  日期：2019.3.4

  A Cu-mediated ortho-C-H radiofluorination of aromatic carboxylic acids that are protected as 8-aminoquinoline benzamides is described. The method uses K18 F and is compatible with a wide range of functional groups. The reaction is showcased in the high specific activity automated synthesis of the RARβ2 agonist [18 F]AC261066.

  描述了被保护为8-氨基喹啉苯甲酰胺的芳香族羧酸的Cu介导的邻位CH氟化。该方法使用K18 F，并且与多种官能团兼容。该反应在RARβ2激动剂[18 F] AC261066的高比活性自动合成中得到展示。
• 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.