1-bromo-2,4-dimethoxy-5-(trifluoromethyl)benzene | 1446436-53-8

• 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: 1-bromo-2,4-dimethoxy-5-(trifluoromethyl)benzene
• CAS: 1446436-53-8
• 化学式: C₉H₈BrF₃O₂
• 分子量: 285.061
• InChiKey: QCNSZZGCDRABNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.49
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  2,4-二甲氧基溴苯 、 [copper(III)(1,10-phenanthroline)(CF₃)₃] 在 potassium pyrosulfate 作用下， 以 二甲基亚砜 为溶剂， 以42 %的产率得到1-bromo-2,4-dimethoxy-5-(trifluoromethyl)benzene
  参考文献：
  名称：

  Direct Arene Trifluoromethylation Enabled by a High‐Valent Cu ^III −CF ₃ Compound

  摘要：

  AbstractDirect C−H trifluoromethylation of arenes and heteroarenes poses an important synthetic challenge that is highly desirable. High‐valent CuIII−CF3compounds have often been invoked in copper‐mediated trifluoromethylation reactions, but the fundamental reactivity toward arenes is elusive. Herein, direct C−H trifluoromethylation of arenes/heteroarenes by a high‐valent CuIII−CF3compound is disclosed for the first time. The CuIII−CF3compound serves CF3radical and a CuIIoxidant by homolytic cleavage of a CuIII−CF3bond, which engage synergistically in a SEAr type reaction with arenes. The presence of K2S2O8co‐oxidant can significantly improve the reaction yields. This reaction shows good efficiency, broad functional group tolerance, and the potential in late‐stage functionalization. The reactivity of high‐valent CuIII−CF3compounds disclosed in this study represents an important progress in organofluorine and CuIIIchemistry.

  DOI：

  10.1002/anie.202209029

文献信息

• Silver-catalysed trifluoromethylation of arenes at room temperature
  作者：Sangwon Seo、John B. Taylor、Michael F. Greaney

  DOI：10.1039/c3cc41829d

  日期：——

  A variety of heteroarenes and electron rich arenes can be trifluoromethylated at room temperature with TMSCF3, catalytic silver and PhI(OAc)2.

  多种杂芳烃和富电子芳烃可以在室温下使用TMSCF3、催化性银和PhI(OAc)2进行三氟甲基化。
• Direct arene trifluoromethylation enabled by promiscuous activity of fungal laccase
  作者：Yi Ling Goh、Shi Yang Preston Long、Mun Fei Eddy Wong、Lee Ling Tan、Elaine Tiong、Fong Tian Wong、Zhennan Liu

  DOI：10.1039/d3ob01779f

  日期：——

  Laccase from Trametes versicolor was found to oxidize non-phenolic arenes and enable the trifluoromethylation of arenes in the presence of in situ generated CF3 radicals at a catalyst loading as low as 0.0034%. The biocatalytic trifluoromethylation proceeded under mild conditions and could increase the yield by up to 12 fold, compared to the control.

  研究发现，来自Trametes versicolor的漆酶可以氧化非酚类芳烃，并在原位生成的CF 3自由基存在下，在催化剂负载量低至0.0034% 的情况下实现芳烃的三氟甲基化。生物催化三氟甲基化在温和条件下进行，与对照相比，产量可提高高达 12 倍。