5-chloro-2-(3-(trifluoromethyl)phenyl)benzo[d]oxazole | 1207429-58-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-chloro-2-(3-(trifluoromethyl)phenyl)benzo[d]oxazole
• 英文别名: 5-Chloro-2-[3-(trifluoromethyl)phenyl]-1,3-benzoxazole；5-chloro-2-[3-(trifluoromethyl)phenyl]-1,3-benzoxazole
• CAS: 1207429-58-0
• 化学式: C₁₄H₇ClF₃NO
• 分子量: 297.664
• InChiKey: VGVHDHLFWYWLEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-(三氟甲基)苯甲酰氯 、 5-氯苯并唑 在 potassium carbonate 作用下， 以 水 、 氯苯 为溶剂， 反应 24.0h， 以71%的产率得到5-chloro-2-(3-(trifluoromethyl)phenyl)benzo[d]oxazole
  参考文献：
  名称：

  Base-Promoted Formal Arylation of Benzo[d]oxazoles with Acyl Chloride

  摘要：

  A base-promoted formal arylation of benzo[d]-oxazoles with acyl chloride was achieved in moderate to good yields. This reaction was triggered by the N-acylation of oxazole to form an iminium intermediate. Then, the addition of H2O to the iminium formed the hemiacetal intermediate. After the sequential ring-opening, extrusion of CO, the ring closure, the dehydration delivered the formal arylation product. In comparison with the transition-metal-catalyzed methodology, it represents an alternative arylation method leading to 2-arylbenzooxazole.

  DOI：

  10.1021/jo402106q

文献信息

• Palladium-Catalyzed Direct Arylations, Alkenylations, and Benzylations through C−H Bond Cleavages with Sulfamates or Phosphates as Electrophiles
  作者：Lutz Ackermann、Sebastian Barfüsser、Jola Pospech

  DOI：10.1021/ol9028034

  日期：2010.2.19

  A catalytic system comprised of Pd(OAc)2 and bidentate ligand dppe enabled first direct arylations with moisture-stable aryl sulfamates as electrophiles, and proved applicable to unprecedented C−H bond functionalizations with easily accessible alkenyl phosphates as well as benzyl phosphates.

  由Pd（OAc）2和二齿配体dppe组成的催化体系能够首先将湿气稳定的芳基氨基磺酸盐作为亲电子试剂进行直接芳基化反应，并证明适用于空前的C-H键官能化，且易于获得的烯基磷酸酯和磷酸苄酯。
• Base-Promoted Formal Arylation of Benzo[<i>d</i>]oxazoles with Acyl Chloride
  作者：Lei Wang、Xinyi Ren、Jintao Yu、Yan Jiang、Jiang Cheng

  DOI：10.1021/jo402106q

  日期：2013.12.6

  A base-promoted formal arylation of benzo[d]-oxazoles with acyl chloride was achieved in moderate to good yields. This reaction was triggered by the N-acylation of oxazole to form an iminium intermediate. Then, the addition of H2O to the iminium formed the hemiacetal intermediate. After the sequential ring-opening, extrusion of CO, the ring closure, the dehydration delivered the formal arylation product. In comparison with the transition-metal-catalyzed methodology, it represents an alternative arylation method leading to 2-arylbenzooxazole.