2-(2,6-dichloro-4-(trifluoromethyl)phenyl)pyrimidine | 1217189-19-9

• 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: 2-(2,6-dichloro-4-(trifluoromethyl)phenyl)pyrimidine
• 英文别名: 2-(2,6-Dichloro-4-(trifluoromethyl)phenyl)pyrimidine；2-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrimidine
• CAS: 1217189-19-9
• 化学式: C₁₁H₅Cl₂F₃N₂
• 分子量: 293.075
• InChiKey: SUQPCAUNGHSLIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-(4-(trifluoromethyl)phenyl)pyrimidine 在 2-(2'-pyrimidyl)phenylpalladium(II) acetate 、 copper(II) trifluoroacetate 、 calcium chloride 作用下， 以 溶剂黄146 为溶剂， 反应 96.0h， 以90%的产率得到2-(2,6-dichloro-4-(trifluoromethyl)phenyl)pyrimidine
  参考文献：
  名称：

  Direct synthesis of ortho-dihalogenated arylpyrimidines using calcium halides as halogen sources

  摘要：

  Pyrimidines and their derivatives have been used as important motifs in materials and medicinal chemistry. In this Letter, a wide variety of ortho-dihalogenated arylpyrimidines were synthesized with high yields and functional-group tolerance using calcium halides as crucial halogenating agents and cupric trifluoroacetate as oxidant in the presence of air. The generated dichlorinated products could be further manipulated by stepwise Suzuki-Miyaura reaction to afford a wide range of ortho-functionalized arylpyrimidines amenable to physical and biological evaluations. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.10.061

文献信息

• Palladium-Catalyzed Monoselective Halogenation of CH Bonds: Efficient Access to Halogenated Arylpyrimidines using Calcium Halides
  作者：Bingrui Song、Xiaojian Zheng、Jun Mo、Bin Xu

  DOI：10.1002/adsc.200900778

  日期：2010.2.15

  A wide variety of ortho-halogenated arylpyrimidines were prepared with high monoselectivity and functional-group tolerance by using calcium halides as crucial halogenating agents and cupric trifluoroacetate as oxidant in the presence of air.

  通过在空气中使用卤化钙作为关键的卤化剂和三氟乙酸铜作为氧化剂，制备了具有高单选择性和官能团耐受性的多种邻卤代芳基嘧啶。
• Copper-catalyzed aromatic C–H bond halogenation with lithium halides under aerobic conditions
  作者：Song Mo、Yamin Zhu、Zengming Shen

  DOI：10.1039/c3ob40185e

  日期：——

  A concise and practical Cu-catalyzed protocol for the preparation of chloro- and bromoarenes via C–H bond activation has been developed. The advantages of this strategy are the employment of cheap Cu(NO3)2·3H2O, LiX and O2, and its compatibility with both electron-donating and electron-withdrawing substituents on aryl rings.

  已经开发了一种简洁实用的Cu催化方案，可通过C–H键激活来制备氯代和溴代芳烃。该策略的优点是使用廉价的Cu（NO 3）2 ·3H 2 O，LiX和O 2，并且它与芳环上的供电子和吸电子取代基兼容。