2-(3-chlorophenyl)-6-methylbenzo[d]thiazole | 1239843-92-5

• 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: 2-(3-chlorophenyl)-6-methylbenzo[d]thiazole
• 英文别名: 2-(3-Chlorophenyl)-6-methyl-1,3-benzothiazole
• CAS: 1239843-92-5
• 化学式: C₁₄H₁₀ClNS
• 分子量: 259.759
• InChiKey: OQPQGQBPMPPBIG-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：
  0.07
• 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：

  2-(3-chlorophenyl)-6-methylbenzo[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93%的产率得到2-(2,6-dibromo-3-chlorophenyl)-6-methylbenzo[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
• 作为产物：
  描述：

  乙烷,三氯氟- 、 3-氯苯乙酮 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 Glauber's salt 、 碘 、 四丁基碘化铵 、 二甲基亚砜 作用下， 以 氯苯 为溶剂， 反应 48.0h， 以67%的产率得到2-(3-chlorophenyl)-6-methylbenzo[d]thiazole
  参考文献：
  名称：

  Efficient 2-aryl benzothiazole formation from acetophenones, anilines, and elemental sulfur by iodine-catalyzed oxidative C(CO)-C(alkyl) bond cleavage

  摘要：

  A novel and efficient iodine-catalyzed one-pot reaction of aromatic amines, acetophenones, and elemental sulfur for the synthesis of 2-aryl benzothiazoles is described. The process involves sequential C-S and C-N bond formation followed by C(CO)-C bond cleavage from readily accessible starting materials. A wide range of functional groups is tolerated under oxidant and metal-free condition and moderate to good product yields are obtained. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2018.08.047

文献信息

• An efficient synthetic route to biologically relevant 2-phenylbenzothiazoles substituted on the benzothiazole ring
  作者：Ashley A. Weekes、Mark C. Bagley、Andrew D. Westwell

  DOI：10.1016/j.tet.2011.08.004

  日期：2011.10

  focus on their unsubstituted ring counterparts. Here we describe a new concise and efficient synthetic route to biologically relevant 2-phenylbenzothiazoles in high yield from the reaction of substituted 2-aminothiophenol disulfides and benzaldehydes, promoted by the inexpensive and non-toxic inorganic oxidant sodium metabisulfite in DMSO at 120 °C. Our new method is tolerant of a range of substituents

  某些在苯并噻唑环上含有取代基的2-苯基苯并噻唑具有重要的生物学特性，但是迄今为止描述的2-苯基苯并噻唑的大多数合成方法都集中在它们的未取代环对应物上。在这里，我们描述了一种新的简洁有效的合成路线，该路线是由廉价的且无毒的无机氧化剂偏亚硫酸氢钠在DMSO中于120°C促进的，是由取代的2-氨基硫代苯酚二硫化物与苯甲醛的反应以高收率获得生物相关的2-苯基苯并噻唑的新方法。我们的新方法可耐受苯并噻唑和苯环上的一系列取代基，并且无需柱色谱即可有效获得取代的2-苯基苯并噻唑。
• 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。
• 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。
• 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.
• Palladium-catalyzed direct ortho-acylation through an oxidative coupling of 2-arylbenzothiazoles with benzylic alcohols
  作者：Qiuping Ding、Huafang Ji、Changqing Ye、Jiajia Wang、Junyan Wang、Liyun Zhou、Yiyuan Peng

  DOI：10.1016/j.tet.2013.08.005

  日期：2013.10

  An efficient protocol was developed for Pd-catalyzed direct C H bond acylation by cross-dehydrogenative-coupling of arylbenzothiazoles and benzylic alcohols using tert-butyl hydroperoxide (TBHP) as the oxidant. The acylation reactions exhibit good reactivities and excellent regioselectivity. (C) 2013 Elsevier Ltd. All rights reserved.