6-bromo-2-(2-chlorophenyl)benzo[d]thiazole | 1235453-34-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 6-bromo-2-(2-chlorophenyl)benzo[d]thiazole
• 英文别名: 6-Bromo-2-(2-chlorophenyl)-1,3-benzothiazole
• CAS: 1235453-34-5
• 化学式: C₁₃H₇BrClNS
• 分子量: 324.628
• InChiKey: FSPLQHCXJGZSHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(2-氯苯基)-1,3-苯并噻唑 在 N-溴代丁二酰亚胺(NBS) 、 silver hexafluoroantimonate 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 作用下， 以 1,2-二氯乙烷 为溶剂， 以92%的产率得到6-bromo-2-(2-chlorophenyl)benzo[d]thiazole
  参考文献：
  名称：

  Rhodium-catalyzed ortho-selective C–H halogenation of 2-arylbenzo[d]thiazoles using N-halosuccinimides as halogen sources

  摘要：

  A series Rh(III)-catalyzed ortho-selective C-H halogenation of 2-arylbenzo[d]thiazoles has been developed using N-halosuccinimides (NXS, X=Br and I) as halogen sources. ortho-Brominated and iodinated various 2-arylbenzo[d]thiazoles could be accessed in good to excellent yields and high regioselectivity under mild reaction conditions. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.03.004

文献信息

• Copper-Catalyzed Activation of Disulfides as a Key Step in the Synthesis of Benzothiazole Moieties
  作者：Jakub Hyvl、Jiri Srogl

  DOI：10.1002/ejoc.201000174

  日期：2010.5

  A convenient synthesis of substituted benzothiazoles has been accomplished by way of a copper catalyzed reaction of aromatic disulfide amines and aldehydes. The process, which involves copper catalyzed activation of disulfide functionality, proceeds in a tandem fashion via C–H bond activation, followed by aerobic oxidation of a resulting dihydrobenzothiazole intermediate. The scope and limitations

  取代苯并噻唑的方便合成已通过芳族二硫化物胺和醛的铜催化反应完成。该过程涉及铜催化二硫化物官能团的活化，通过 C-H 键活化以串联方式进行，然后对所得二氢苯并噻唑中间体进行有氧氧化。反应的范围和局限性在各种底物上得到证明。
• Regioselective One-Pot Synthesis of 2-Aryl-6-bromobenzothiazole from Arylaldehyde and 2-Aminothiophenol with Phenyltrimethylammonium Tribromide in the Presence of a Catalytic Amount of Antimony(III) Bromide
  作者：Shinsei Sayama

  DOI：10.3987/com-11-12178

  日期：——

  Various 2-aryl-6-bromo-1,3-benzothiazoles were regioselectively afforded in good yields by the reaction of arylaldehydes and 2-aminothiophenol with phenyltrimethylammonium tribromide in the presence of a catalytic amount of SbBr(3) in CH(2)Cl(2) at room temperature.
• Rhodium-catalyzed ortho-selective C–H halogenation of 2-arylbenzo[d]thiazoles using N-halosuccinimides as halogen sources
  作者：Qiuping Ding、Xiaoli Zhou、Shouzhi Pu、Banpeng Cao

  DOI：10.1016/j.tet.2015.03.004

  日期：2015.4

  A series Rh(III)-catalyzed ortho-selective C-H halogenation of 2-arylbenzo[d]thiazoles has been developed using N-halosuccinimides (NXS, X=Br and I) as halogen sources. ortho-Brominated and iodinated various 2-arylbenzo[d]thiazoles could be accessed in good to excellent yields and high regioselectivity under mild reaction conditions. (C) 2015 Elsevier Ltd. All rights reserved.