2-(2-氯苯磺酰基)苯并噻唑 | 60372-34-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: 2-(2-氯苯磺酰基)苯并噻唑
• 英文名称: 2-((2-chlorophenyl)thio)benzo[d]thiazole
• 英文别名: 2-(2-Chlorophenylsulfanyl)benzothiazole；2-(2-chlorophenyl)sulfanyl-1,3-benzothiazole
• CAS: 60372-34-1
• 化学式: C₁₃H₈ClNS₂
• 分子量: 277.798
• InChiKey: UNGVMFFINJFURC-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：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为产物：
  描述：

  2-巯基苯并噻唑 在 potassium hydroxide 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 0.53h， 生成 2-(2-氯苯磺酰基)苯并噻唑
  参考文献：
  名称：

  New Synthesis and Biological Evaluation of Benzothiazole Derivates as Antifungal Agents

  摘要：

  In search of new antifungal agrochemicals that could replace commercially available, aryl-2-mercaptobenzothiazoles were synthesized. They were prepared by two methodologies, using both photostimulated reaction and microwave assisted reaction. These reactions took place without the use of metallic catalyst by a one-pot procedure with excellent yields (70-98%). Synthesized compounds were evaluated for fungal growth inhibition against Botrytis cinerea. Most of the compounds have an excellent antifungal activity, and three of these showed a superior inhibitory effect to commercial fungicide Triadimefon. IC50 values observed for 2-(phenylthio)benzothiazole, 2-(2-chlorophenylthio)benzothiazole, and 2-(3-chlorophenyl thio)benzothiazole were 0.75, 0.69, and 0.65 μg mL(-1), respectively.

  DOI：

  10.1021/acs.jafc.5b00150

文献信息

• Copper(I)-Catalyzed Tandem One-Pot Synthesis of 2-Arylthiobenzothiazoles and 2-Arylthiobenzoxazoles in Water
  作者：Xing Liu、Shi-Bo Zhang、Hui Zhu、Zhi-Bing Dong

  DOI：10.1021/acs.joc.8b01644

  日期：2018.10.5

  efficient tandem process for the preparation of 2-arylthiobenzothiazoles has been developed. By condensation of 2-aminobenzenethiol with tetramethylthiuram disulfide (TMTD), 2-mercaptobenzothiazoles was in situ generated, which susequently underwent coupling with iodobenzenes to give the desired 2-arylthiobenzothiazoles fluently in a one-pot manner. This method can also be used for the synthesis of 2-

  已经开发了用于制备2-芳基硫代苯并噻唑的有效串联方法。通过2-氨基苯硫醇与四甲基秋兰姆二硫化物（TMTD）的缩合，原位生成2-巯基苯并噻唑，其随后与碘代苯偶合，以单锅方式流畅地得到所需的2-芳基硫代苯并噻唑。该方法也可用于合成2-芳基硫代苯并恶唑。廉价的金属催化剂和配体，温和的反应温度以及水作为溶剂，使该方案在有机合成中具有实用价值和实用性。
• Ru‐catalyzed Formation of Thiosilanes and Selenosilanes using Dichalcogenides as a User‐Friendly Alternative to Thiols and Selenols
  作者：Krzysztof Kuciński、Marcin Gruszczyński、Grzegorz Hreczycho

  DOI：10.1002/cctc.202200961

  日期：2022.10.10

  The silylation/germylation of several disulfides/diselenides has been established by using commercially available ruthenium catalyst. As a result, several silylthioethers and their germanium and selenium analogs have been synthesized. Notably, the obtained thiosilanes were subsequently utilized in nucleophilic aromatic substitution reaction, leading to unsymmetrical sulfides.

  通过使用市售的钌催化剂已经建立了几种二硫化物/二硒化物的甲硅烷基化/胚芽化。结果，合成了几种甲硅烷基硫醚及其锗和硒类似物。值得注意的是，得到的硫硅烷随后被用于亲核芳族取代反应，导致硫化物不对称。
• The Direct Thiolation of Benzothiazole Catalyzed by Copper Complex in Superbase System
  作者：Yu Yuan、Xiaowei Wang、Yanjun Li

  DOI：10.1055/s-0032-1316891

  日期：——

  The copper-catalyzed direct thiolation of benzothiazole with iodobenzene and sulfur in superbase system under oxygen atmosphere is reported. The corresponding 2-thio-substituted benzothiazoles were formed in satisfactory yields.
• Copper Oxide Nanoparticle-Catalyzed Chalcogenation of the Carbon-Hydrogen Bond in Thiazoles: Synthesis of 2-(Organochalcogen)thiazoles
  作者：Alisson R. Rosario、Kamila K. Casola、Carla E. S. Oliveira、Gilson Zeni

  DOI：10.1002/adsc.201300497

  日期：2013.10.11

  AbstractWe present (homepage: www.ufsm.br) herein the application of copper nanoparticles/diorganyl dichalcogenides to promote the synthesis of 2‐(organochalcogen)thiazoles via direct carbon‐hydrogen bond activation in thiazoles. A systematic study of the catalytic system revealed that the presence and amount of base played an essential role in this reaction. The results revealed that electron‐donating and electron‐withdrawing substituents, in the aromatic ring bonded to the chalcogen atom of diorganyl dichalcogenides, required one equiv. of base, while when neutral substituents were present two equiv. of base were needed to deliver the products in similar yields.magnified image
• 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.