N-(4-bromo-2,6-dipropylbenzoyl)-8-aminoquinoline | 1215019-00-3

• 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: N-(4-bromo-2,6-dipropylbenzoyl)-8-aminoquinoline
• CAS: 1215019-00-3
• 化学式: C₂₂H₂₃BrN₂O
• 分子量: 411.341
• InChiKey: VHHFKOHDEWBXTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.15
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  41.99
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-(4-bromo-2,6-dipropylbenzoyl)-8-aminoquinoline 在 硫酸 、 水 作用下， 反应 24.0h， 以95%的产率得到4-bromo-2,6-dipropylbenzoic acid
  参考文献：
  名称：

  Auxiliary-Assisted Palladium-Catalyzed Arylation and Alkylation of sp² and sp³ Carbon−Hydrogen Bonds

  摘要：

  We have developed a method for auxiliary-directed, palladium-catalyzed beta-arylation and alkylation of sp(3) and sp(2) C-H bonds in carboxylic acid derivatives. The method employs a carboxylic acid 2-methylthioaniline- or 8-aminoquinoline amide substrate, aryl or alkyl iodide coupling partner, palladium acetate catalyst, and an inorganic base. By employing 2-methylthioaniline auxiliary, selective monoarylation of primary sp(3) C-H bonds can be achieved. If arylation of secondary sp(3) C-H bonds is desired, 8-aminoquinoline auxiliary may be used. For alkylation of sp(3) and sp(2) C-H bonds, 8-aminoquinoline auxiliary affords the best results. Some functional group tolerance is observed and amino- and hydroxy-acid derivatives can be functionalized. Preliminary mechanistic studies have been performed. A palladacycle intermediate has been isolated, characterized by X-ray crystallography, and its reactions have been studied.

  DOI：

  10.1021/ja910900p
• 作为产物：
  描述：

  4-bromo-N-quinolin-8-ylbenzamide 、 1-碘代丙烷 在 palladium diacetate 、 potassium carbonate 、 三甲基乙酸 作用下， 以 2-甲基-2-丁醇 为溶剂， 反应 12.5h， 以77%的产率得到N-(4-bromo-2,6-dipropylbenzoyl)-8-aminoquinoline
  参考文献：
  名称：

  Auxiliary-Assisted Palladium-Catalyzed Arylation and Alkylation of sp² and sp³ Carbon−Hydrogen Bonds

  摘要：

  We have developed a method for auxiliary-directed, palladium-catalyzed beta-arylation and alkylation of sp(3) and sp(2) C-H bonds in carboxylic acid derivatives. The method employs a carboxylic acid 2-methylthioaniline- or 8-aminoquinoline amide substrate, aryl or alkyl iodide coupling partner, palladium acetate catalyst, and an inorganic base. By employing 2-methylthioaniline auxiliary, selective monoarylation of primary sp(3) C-H bonds can be achieved. If arylation of secondary sp(3) C-H bonds is desired, 8-aminoquinoline auxiliary may be used. For alkylation of sp(3) and sp(2) C-H bonds, 8-aminoquinoline auxiliary affords the best results. Some functional group tolerance is observed and amino- and hydroxy-acid derivatives can be functionalized. Preliminary mechanistic studies have been performed. A palladacycle intermediate has been isolated, characterized by X-ray crystallography, and its reactions have been studied.

  DOI：

  10.1021/ja910900p