N-[2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl]-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide | 1352238-53-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl]-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide
• CAS: 1352238-53-9
• 化学式: C₂₀H₁₇BF₇NO₃
• 分子量: 463.16
• InChiKey: QMCZFCGKAVWDHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.81
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  N-[2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl]-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide 在 copper(ll) bromide 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 以91%的产率得到2-bromo-N-[2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl]benzamide
  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：

  N-(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)benzamide 、 联硼酸频那醇酯 在 Pd(MeCN)2(OTf)2 K₂S₂O₈ 、 TsONa 作用下， 以 乙腈 为溶剂， 生成 N-[2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl]-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide
  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

文献信息

• Pd-Catalyzed Oxidative <i>ortho</i>-C–H Borylation of Arenes
  作者：Hui-Xiong Dai、Jin-Quan Yu

  DOI：10.1021/ja2097095

  日期：2012.1.11

  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.