2-((3,5-dimethylphenyl)thio)benzo[d]thiazole | 1335609-16-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-((3,5-dimethylphenyl)thio)benzo[d]thiazole
• 英文别名: 2-(3,5-Dimethylphenyl)sulfanyl-1,3-benzothiazole
• CAS: 1335609-16-9
• 化学式: C₁₅H₁₃NS₂
• 分子量: 271.407
• InChiKey: QROPXSZKFOKYKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  66.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3,5-二甲基溴苯 、 2-巯基苯并噻唑 在 copper(l) iodide 、 sodium hydroxide 作用下， 反应 24.0h， 以90%的产率得到2-((3,5-dimethylphenyl)thio)benzo[d]thiazole
  参考文献：
  名称：

  Novel copper/PEG-400 catalyst systems for chemoselective S- and N-arylation of 2-mercaptobenzothiazole

  摘要：

  A novel approach for chemoselective S- and N-arylation of 2-mercaptobenzothiazole was developed by copper/PEG-400 catalyst systems. Copper source and reaction temperature play an important role in this protocol, selective S-arylation of 2-mercaptobenzothiazole was achieved by using CuI/PEG-400/50 degrees C catalyst system, while selective N-arylation was achieved with CuO/PEG-400/140 degrees C catalyst system. Both are compatible with a variety of aryl halides and selectively give the desired S- and N-arylation products in good to excellent yields, respectively. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.10.075

文献信息

• Copper-Mediated C–H Activation/C–S Cross-Coupling of Heterocycles with Thiols
  作者：Sadananda Ranjit、Richmond Lee、Dodi Heryadi、Chao Shen、Ji’En Wu、Pengfei Zhang、Kuo-Wei Huang、Xiaogang Liu

  DOI：10.1021/jo2017444

  日期：2011.11.4

  oles by direct thiolation of benzothiazoles with aryl or alkyl thiols via copper-mediated aerobic C–H bond activation in the presence of stoichiometric CuI, 2,2′-bipyridine and Na2CO3. We also show that the approach can be extended to thiazole, benzimidazole, and indole substrates. In addition, we present detailed mechanistic investigations on the Cu(I)-mediated direct thiolation reactions. Both computational

  我们报告了在化学计量的CuI，2,2'-联吡啶存在下，通过铜介导的需氧C–H键活化，通过苯并噻唑与芳基或烷基硫醇的直接硫醇化反应，合成了一系列芳基或烷基取代的2-巯基苯并噻唑和Na 2 CO 3。我们还表明该方法可以扩展到噻唑，苯并咪唑和吲哚底物。此外，我们目前对Cu（I）介导的直接硫醇化反应的详细机理研究。计算研究和实验结果均表明，铜-硫醇盐络合物[（L）Cu（SR）]（L：基于氮的双齿配体，例如2,2'-联吡啶； R：芳基或烷基）是第一反应性负责观察到的有机转化的中间体。此外，我们的计算研究表明，基于氢原子提取途径的逐步反应机理，比包括β-氢化物消除，单电子转移，氢原子转移，氧化加/还原消除和σ在内的许多其他可能途径在能量上更可行。键易位。
• Ag–Cu copromoted direct C2–H bond thiolation of azoles with Bunte salts as sulfur sources
  作者：Rui Wang、Hongyan Xu、Ying Zhang、Yuntao Hu、Yingsu Wei、Xiao Du、Huaiqing Zhao

  DOI：10.1039/d1ob00823d

  日期：——

  A direct C2–H thiolation of azoles with Bunte salts was achieved under the combined action of copper and silver salts, furnishing various substituted 2-thioazoles in moderate to good yields.

  使用铜盐和银盐的共同作用，实现了与Bunte盐的直接C2-H硫化作用，在中等到良好的产率下提供了各种取代的2-硫代咪唑。
• Novel copper/PEG-400 catalyst systems for chemoselective S- and N-arylation of 2-mercaptobenzothiazole
  作者：Xiaokang Li、Tangjun Yuan、Yu Yang、Junmin Chen

  DOI：10.1016/j.tet.2014.10.075

  日期：2014.12

  A novel approach for chemoselective S- and N-arylation of 2-mercaptobenzothiazole was developed by copper/PEG-400 catalyst systems. Copper source and reaction temperature play an important role in this protocol, selective S-arylation of 2-mercaptobenzothiazole was achieved by using CuI/PEG-400/50 degrees C catalyst system, while selective N-arylation was achieved with CuO/PEG-400/140 degrees C catalyst system. Both are compatible with a variety of aryl halides and selectively give the desired S- and N-arylation products in good to excellent yields, respectively. (C) 2014 Elsevier Ltd. All rights reserved.