2-m-chlorophenylsulfanyl-benzothiazole | 119993-76-9

• 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-m-chlorophenylsulfanyl-benzothiazole
• 英文别名: 2-((3-chlorophenyl)thio)benzo[d]thiazole；2-(3-Chlorophenyl)sulfanyl-1,3-benzothiazole
• CAS: 119993-76-9
• 化学式: C₁₃H₈ClNS₂
• 分子量: 277.798
• InChiKey: NAWOJCTZPWDWRQ-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

反应信息

• 作为产物：
  描述：

  2-巯基苯并噻唑 在 四丁基溴化铵 、 potassium hydroxide 作用下， 以 水 为溶剂， 反应 0.15h， 生成 2-m-chlorophenylsulfanyl-benzothiazole
  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-Catalyzed One-Pot Synthesis of Chalcogen-Benzothiazoles/Imidazo[1,2-a]pyridines with Sulfur/Selenium Powder and Aryl Boronic Acids
  作者：Tao Guo、Shu-Lei Han、Yong-Cheng Ma、Xu-Ning Wei、Ying-Li Zhu、Huan Chen

  DOI：10.1055/s-0037-1609758

  日期：2018.7

  An efficient and convenient copper-catalyzed oxidative chalcogenation of benzothiazoles and imidazo[1,2-a]pyridines with sulfur/selenium powder and aryl boronic acids was developed. This procedure allows access to a wide range of structurally diverse arylchalcogen-substituted benzothiazoles/imidazo[1,2-a]pyridines in good yields and with good functional group tolerance. A biological evaluation revealed

  开发了一种有效且方便的铜催化苯并噻唑和咪唑并 [1,2-a] 吡啶与硫/硒粉末和芳基硼酸的氧化硫属元素。该程序允许以良好的产率和良好的官能团耐受性获得各种结构多样的芳基硫属元素取代的苯并噻唑/咪唑并 [1,2-a] 吡啶。生物学评估表明，一些获得的产品在体外对人源性肺、胃、食管和乳腺癌细胞系具有抗增殖活性。
• Photo-induced copper-catalyzed C–H chalcogenation of azoles at room temperature
  作者：Parthasarathy Gandeepan、Jiayu Mo、Lutz Ackermann

  DOI：10.1039/c7cc03107f

  日期：——

  Inexpensive copper catalysts enabled direct C–H chalcogenations at ambient temperature by means of photo-induced catalysis. The expedient copper catalysis set the stage for C–S and C–Se bond formation from readily accessible non-volatile elemental chalcogens. The photo-assisted copper catalysis manifold proved suitable for a wide range of substrates with good functional group tolerance and exhibited

  廉价的铜催化剂可通过光诱导催化在环境温度下直接进行C–H硫属元素化作用。方便的铜催化作用为容易获得的非挥发性元素硫属元素形成C–S和C–Se键奠定了基础。事实证明，光辅助铜催化歧管适用于具有良好官能团耐受性的各种基材，即使在25°C的反应温度下也显示出高催化效率。
• 15-Membered Macrocyclic Schiff-Base-Pd(0) Complex Immobilized on Fe3O4 MNPs: An Novel Nanomagnetic Catalyst for the One-Pot Three-Component C–H Chalcogenation of Azoles by S8 and Aryl Iodides
  作者：Jin Liu、Shaofen Jin、Sanhai Qin、Jingjing Du、Yingxing Zhou、Bingcun Cui、Xing Kang、Xiangyang Zhang

  DOI：10.1007/s10562-022-04194-x

  日期：——

  This fact that diaryl sulfides are important structural components in polymers, agrochemicals, natural products, and pharmaceutical intermediates has increased the attention of chemists to synthesize these compounds. In recent times, the research on the preparation of diaryl sulfides using magnetically reusable catalysts have received profound attention in organic chemistry. In this paper, we describe

  二芳基硫醚是聚合物、农用化学品、天然产物和药物中间体中重要的结构成分，这一事实增加了化学家对合成这些化合物的关注。近年来，利用磁性可重复使用催化剂制备二芳基硫醚的研究在有机化学领域受到了广泛关注。在本文中，我们描述了磁性可重复使用的钯纳米材料的制备和表征，并评估了其通过唑类、S 8的一锅三组分偶联反应制备二芳基硫醚的催化活性。和芳基碘化物。通过一系列光谱技术，包括 FT-IR、SEM、TEM、EDX、XRD、VSM、TGA、ICP-OES 等，对磁性纳米粒子负载的钯的结构进行了很好的表征。据我们所知，这是首次利用Pd纳米磁性催化剂进行唑类、S 8和芳基碘化物的一锅三组分偶联反应的报道。 图形概要
• 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.
• Intra- and Intermolecular C−S Bond Formation Using a Single Catalytic System: First Direct Access to Arylthiobenzothiazoles
  作者：Siva Murru、Harisadhan Ghosh、Santosh K. Sahoo、Bhisma K. Patel

  DOI：10.1021/ol9017535

  日期：2009.10.1

  We have for the first time developed two ligand-assisted Cu(I)-catalyzed sequential intra- and intermolecular Sarylations leading to the direct synthesis of arylthiobenzothiazoles in one pot without an inert atmosphere. Low catalyst loading, inexpensive metal catalyst and ligand, lower reaction temperature, and shorter reaction times make this method superior to all reported methods for the synthesis of arylthiobenzothiazole.