2-(perfluorophenyl)-4,5,6a,7-tetrahydro-dibenzo[de,g]quinoline-6-carboxylic acid tert-butyl ester

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 阿朴菲
• 英文名称: 2-(perfluorophenyl)-4,5,6a,7-tetrahydro-dibenzo[de,g]quinoline-6-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl 2-(2,3,4,5,6-pentafluorophenyl)-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-6-carboxylate
• 化学式: C₂₇H₂₂F₅NO₂
• 分子量: 487.469
• InChiKey: AGMDZMWWZARKEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  35
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-chloro-4,5,6a,7-tetrahydro-dibenzo[de,g]quinoline-6-carboxylic acid tert-butyl ester 、 五氟苯 在 2-双环己基膦-2',6'-二甲氧基联苯 、 palladium diacetate 、 potassium carbonate 作用下， 以 醋酸异丙酯 为溶剂， 反应 12.0h， 以99%的产率得到2-(perfluorophenyl)-4,5,6a,7-tetrahydro-dibenzo[de,g]quinoline-6-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Mild and General Conditions for the Cross-Coupling of Aryl Halides with Pentafluorobenzene and Other Perfluoroaromatics

  摘要：

  New reaction conditions are described that enable the direct arylation of pentafluorobenzene with sterically encumbered aryl bromides and aryl chlorides. These reactions occur in high yield and under mild conditions. Notably, the reactions can be performed at 80 C in isopropyl acetate with a catalyst generated by the in situ mixing of Pd(OAc)(2) and S-Phos. The enhanced scope of these transformations should further reduce the need to use pentafluorophenylboronic acid in the construction of perfluoroarenes.

  DOI：

  10.1021/ol0619967

文献信息

• Mild and General Conditions for the Cross-Coupling of Aryl Halides with Pentafluorobenzene and Other Perfluoroaromatics
  作者：Marc Lafrance、Daniel Shore、Keith Fagnou

  DOI：10.1021/ol0619967

  日期：2006.10.1

  New reaction conditions are described that enable the direct arylation of pentafluorobenzene with sterically encumbered aryl bromides and aryl chlorides. These reactions occur in high yield and under mild conditions. Notably, the reactions can be performed at 80 C in isopropyl acetate with a catalyst generated by the in situ mixing of Pd(OAc)(2) and S-Phos. The enhanced scope of these transformations should further reduce the need to use pentafluorophenylboronic acid in the construction of perfluoroarenes.