6-chloro-2-(2-chlorophenyl)benzo[d]thiazole | 15952-12-2

• 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-chloro-2-(2-chlorophenyl)benzo[d]thiazole
• 英文别名: 6-Chloro-2-(2-chlorophenyl)-1,3-benzothiazole；6-chloro-2-(2-chlorophenyl)-1,3-benzothiazole
• CAS: 15952-12-2
• 化学式: C₁₃H₇Cl₂NS
• 分子量: 280.177
• InChiKey: NPTBANVUGCCPEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 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

• 作为反应物：
  描述：

  6-chloro-2-(2-chlorophenyl)benzo[d]thiazole 在 四(三苯基膦)钯 、 N-氟代双苯磺酰胺 、 L-脯氨酸 作用下， 以 环己烷 为溶剂， 反应 5.0h， 以71%的产率得到6-chloro-2-(2-chloro-6-fluorophenyl)benzo[d]thiazole
  参考文献：
  名称：

  Pd(PPh3)4-catalyzed direct ortho-fluorination of 2-arylbenzothiazoles with an electrophilic fluoride N-fluorobenzenesulfonimide (NFSI)

  摘要：

  An efficient protocol was developed for regio-selective Pd-catalyzed direct ortho-fluorination of 2-alylbenzo[d]thiazoles using N-fluorobenzenesulfonimide (NFSI) as the F+ source, and L-proline as the crucial promoter. The present method offered a practical route to synthesize valuable fluorinated products, which are of potential importance in the pharmaceutical and agrochemical industries. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.11.034

文献信息

• Substrate-assisted rhodium-catalyzed C H bond cyanation of 2-arylbenzothiazoles
  作者：Yuanyuan Ping、Qiuping Ding、Zhaobin Chen、Yiyuan Peng

  DOI：10.1016/j.jorganchem.2016.04.034

  日期：2016.8

  A mild and efficient substrate-assisted CH bond cyanation of 2-arylbenzothiazoles has been developed using CuCN as cyano-group source. The reaction exhibits broad functional groups tolerance giving the desired products in moderate to excellent yields. Regioselective cyanation was in favor of the less sterically hindered position to those meta-substituted substrate.

  使用CuCN作为氰基源，已经开发出了温和有效的2-芳基苯并噻唑的基质辅助CH键氰化方法。该反应显示出宽泛的官能团耐受性，以中等至极好的产率提供所需产物。区域选择性氰化有利于那些间位取代的底物的空间位阻较小。
• Regioselective ortho-trifluoromethylthiolation of 2-arylbenzo[d]thiazole via tandem substrate-assisted C–H iodination and trifluoromethylthiolation
  作者：Puying Luo、Qiuping Ding、Yuanyuan Ping、Jianan Hu

  DOI：10.1039/c6ob00005c

  日期：——

  A mild and efficient tandem benzo[d]thiazole directed C–H iodination and trifluoromethylthiolation for the synthesis ofortho-trifluoromethylthiolated 2-arylbenzo[d]thiazoles have been developed using AgSCF₃as a coupling partner.

  通过使用AgSCF₃作为偶联试剂，开发了一种温和高效的串联苯并[d]噻唑定向C-H碘化和三氟甲硫基化合成ortho-三氟甲硫基化2-芳基苯并[d]噻唑的方法。
• Palladium-catalyzed C–H bond functionalization/oxidative acyloxylation of 2-aryl-benzo[d]thiazoles
  作者：Qiuping Ding、Huafang Ji、Ziyi Nie、Qin Yang、Yiyuan Peng

  DOI：10.1016/j.jorganchem.2013.04.026

  日期：2013.9

  A chelation-assisted Pd-catalyzed ortho-acyloxylation reaction of the 2-arylbenzo[d]thiazole is described via sp2 C–H bond activation. A wide substrate scope with good functional group tolerance has been demonstrated, affording mono- or diacyloxylation products in moderate to good yields. This method is an alternative route for the preparation of 2-arylbenzo[d]thiazole derivatives via a C–H activation

  通过sp 2 C–H键活化描述了2-芳基苯并[ d ]噻唑的螯合辅助Pd催化邻位酰氧基化反应。已经证明具有良好的官能团耐受性的广泛的底物范围，以中等至良好的产率提供了单或二酰氧基化产物。该方法是通过CH活化机理制备2-芳基苯并[ d ]噻唑衍生物的另一种方法。
• Pd-catalysed <i>ortho</i>-C-H Acylation/cross Coupling of 2-arylbenzo[d]thiazoles with Aldehydes Using <i>tert</i>-butyl Hydroperoxide as Oxidant
  作者：Jian Wang、Ziyi Nie、Yan Li、Shuang Tan、Jiantao Jiang、Pusheng Jiang、Qiuping Ding

  DOI：10.3184/174751913x13639769724276

  日期：2013.5

  An efficient palladium-catalysed protocol for direct C–H bond acylation by cross coupling of 2-arylbenzo[d]thiazoles and aldehydes using tert-butyl hydroperoxide as the oxidant is reported. The process provides a useful method for the synthesis of aromatic ketones directly from aldehydes. In addition, the reaction can tolerate various functional groups in good yield with high regioselectivity.

  报道了使用叔丁基过氧化氢作为氧化剂通过 2-芳基苯并 [d] 噻唑和醛的交叉偶联直接 C-H 键酰化的有效钯催化方案。该方法为直接从醛合成芳香酮提供了一种有用的方法。此外，该反应可以以良好的收率和高区域选择性耐受各种官能团。
• 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.