6-fluoro-2-(m-tolyl)benzo[d]thiazole

• 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-fluoro-2-(m-tolyl)benzo[d]thiazole
• 英文别名: 6-Fluoro-2-(3-methylphenyl)-1,3-benzothiazole
• 化学式: C₁₄H₁₀FNS
• 分子量: 243.305
• InChiKey: RCDGIWPXUSIYCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  41.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-fluoro-2-(m-tolyl)benzo[d]thiazole 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89%的产率得到2-(2-bromo-5-methylphenyl)-6-fluorobenzo[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

• Synthesis of 2-Arylbenzothiazole and 2-Arylthiazole Derivatives via a Ru-Catalyzed <i>meta</i>-Selective C–H Nitration Reaction
  作者：Deming Liu、Puying Luo、Junying Ge、Zilin Jiang、Yiyuan Peng、Qiuping Ding

  DOI：10.1021/acs.joc.9b01194

  日期：2019.10.18

  A Ru-catalyzed meta-selective C-H nitration of 2-arylbenzothiazoles and 2-arylthiazoles has been developed. A wide range of functional groups are tolerated, providing the meta-nitrated products in good to excellent yields using Cu(NO3)2·3H2O as the nitro source. The nitration could be carried out on a gram scale and used for the synthesis of promising therapeutic leads for human African trypanosomiasis

  已经开发了Ru催化的2-芳基苯并噻唑和2-芳基噻唑的亚选择性CH硝化反应。可以容忍各种官能团，使用Cu（NO3）2·3H2O作为硝基源，可以提供高至极佳收率的亚硝化产物。硝化作用可以以克为单位进行，并用于合成人类非洲锥虫病的有希望的治疗先导。
• 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。
• Process for producing biaryl compound
  申请人：Hagiya Koji

  公开号：US20050096471A1

  公开（公告）日：2005-05-05

  A process for producing a biaryl compound, characterized by reacting an arylhydrazine compound, hydrogen peroxide and an aryl compound. When the reaction is conducted in the presence of a given metal or a compound of the metal or in the presence of a metal oxide obtained by reacting the given metal or a compound of the metal with hydrogen peroxide, then the yield of the biaryl compound is improved.

  一种生产双芳基化合物的工艺，其特征在于使芳基肼化合物、过氧化氢和芳基化合物反应。当反应是在某种金属或金属化合物存在下进行，或在某种金属或金属化合物与过氧化氢反应得到的金属氧化物存在下进行时，双芳基化合物的产率会提高。
• Pd(PPh3)4-catalyzed direct ortho-fluorination of 2-arylbenzothiazoles with an electrophilic fluoride N-fluorobenzenesulfonimide (NFSI)
  作者：Qiuping Ding、Changqing Ye、Shouzhi Pu、Banpeng Cao

  DOI：10.1016/j.tet.2013.11.034

  日期：2014.1

  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.