N-[2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl]naphthalene-2-carboxamide | 1352238-52-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-[2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl]naphthalene-2-carboxamide
• CAS: 1352238-52-8
• 化学式: C₁₈H₈F₇NO
• 分子量: 387.256
• InChiKey: INMPOSQHWKLYRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-[2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl]naphthalene-2-carboxamide 、 联硼酸频那醇酯 在 dipotassium peroxodisulfate 、 1,5-二(4-三氟甲基苯基)-戊-1,4-二烯-3-酮 、 palladium diacetate 、 对甲苯磺酸钠 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以72%的产率得到N-[2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl]-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalene-2-carboxamide
  参考文献：
  名称：

  Pd-Catalyzed Oxidative ortho-C–H Borylation of Arenes

  摘要：

  The development of a Pd-catalyzed oxidative ortho-C-H borylation with N-arylbenzamides is reported. A modified dibenzylideneacetone (dba) ligand, a weak base, and a strong oxidant are critical for obtaining good yields. The reaction is tolerant of electron-deficient and electron-rich benzamides derived from readily available benzoic acids. The borylated products can be converted to various synthons via diverse transformations.

  DOI：

  10.1021/ja2097095
• 作为产物：
  描述：

  4-氨基七氟甲苯 、 2-萘甲酰氯 以 甲苯 为溶剂， 生成 N-[2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl]naphthalene-2-carboxamide
  参考文献：
  名称：

  Pd(II)-Catalyzed Ortho Trifluoromethylation of Arenes and Insights into the Coordination Mode of Acidic Amide Directing Groups

  摘要：

  A Pd(II)-catalyzed trifluoromethylation of ortho C-H bonds with an array of N-arylbenzamides derived from benzoic acids is reported. N-Methylformamide has been identified as a crucial promoter of C-CF3 bond formation from the Pd center. X-ray characterization of the C-H insertion intermediate has revealed a rare coordination mode of acidic amides as directing groups and the origin of their capacity in directing C-H activation.

  DOI：

  10.1021/ja305259n