2-(o-tolylthio)benzo[d]thiazole

• 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-(o-tolylthio)benzo[d]thiazole
• 英文别名: 2-(2-Methylphenyl)sulfanyl-1,3-benzothiazole；2-(2-methylphenyl)sulfanyl-1,3-benzothiazole
• 化学式: C₁₄H₁₁NS₂
• 分子量: 257.38
• InChiKey: KDQNAXPWFSFUFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 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-氨基苯硫醇 在 1,10-菲罗啉 、 potassium carbonate 、 copper(I) bromide 作用下， 以 水 为溶剂， 反应 18.0h， 生成 2-(o-tolylthio)benzo[d]thiazole
  参考文献：
  名称：

  铜（I）催化串联一锅法合成水中的2-芳硫基苯并噻唑和2-芳硫基苯并恶唑

  摘要：

  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。

  DOI：

  10.1021/acs.joc.8b01644

文献信息

• Visible-Light-Mediated Synthesis of Unsymmetrical Diaryl Sulfides via Oxidative Coupling of Arylhydrazine with Thiol
  作者：Golam Kibriya、Susmita Mondal、Alakananda Hajra

  DOI：10.1021/acs.orglett.8b03549

  日期：2018.12.7

  A metal-free visible-light-promoted oxidative coupling between thiols and arylhydrazines has been developed to afford diaryl sulfides using a catalytic amount of rose bengal as photocatalyst under aerobic conditions. A library of unsymmetrical diaryl sulfides with broad functionalities was synthesized in good yields at room temperature. The present methodology is also applicable to benzo[ d]thiazole-2-thiols

  已经开发出在硫醇和芳基肼之间的无金属的可见光促进的氧化偶合，以在有氧条件下使用催化量的孟加拉红作为光催化剂来提供二芳基硫醚。在室温下以高收率合成了具有广泛功能的不对称二芳基硫醚库。本方法学也适用于苯并[d]噻唑-2-硫醇，苯并[d]恶唑-2-硫醇，1 H-苯并[d]咪唑-2-硫醇和1 H-咪唑-2-硫醇。
• Mechanochemical Nickel‐Catalyzed Carbon‐Sulfur Bond Formation between Aryl Iodides and Aromatic Sulfur Surrogates
  作者：Xiujia Hao、Daming Feng、Hongguang Chen、Peng Huang、Fang Guo

  DOI：10.1002/chem.202302119

  日期：2023.10.26

  and mild carbon-sulfur coupling was realized by nickel catalysis under ball-milling conditions. The desired thioether products were generated from aryl iodides and aromatic thiol/disulfides with broad substrate scope. The Ni(i)/Ni(III) catalytic cycle was facilitated by the mechanochemistry process, thus providing an eco-friendly and time-saving strategy for the construction of the C−S bond in practical

  在球磨条件下通过镍催化实现了绿色温和的碳硫偶联。所需的硫醚产物由具有广泛底物范围的芳基碘化物和芳香族硫醇/二硫化物生成。机械化学过程促进了Ni(i)/Ni(III)催化循环，从而为实际合成化学中C−S键的构建提供了一种环保且省时的策略。
• Fe₃O₄@ABA-aniline-CuI nanocomposite as a highly efficient and reusable nanocatalyst for the synthesis of benzothiazole-sulfide aryls and heteroaryls
  作者：Mingzhe Sun、Wei Liu、Wei Wu、Qun Li、Li Shen

  DOI：10.1039/d3ra03069e

  日期：——

  difficult reactions and the synthesis of complexed molecules such as benzothiazole-sulfide aryls. In this work, CuI was successfully immobilized on the surface of magnetic Fe3O4 nanoparticles modified with aniline and 4-aminobenzoic acid [Fe3O4@ABA-Aniline-CuI nanocomposite] and its catalytic activity was investigated in the preparation of a broad range of benzothiazole-sulfide aryls and heteroaryls through

  研究二芳基硫醚和苯并噻唑在有机合成中很重要，因为许多天然和医药产品都含有这些支架。近年来，含有苯并噻唑硫芳基化合物作为重要的生物分子的合成研究受到了广泛关注。多组分反应是执行困难反应和合成复杂分子（例如苯并噻唑-硫化物芳基）的最流行的策略。在这项工作中，CuI 成功固定在苯胺和 4-氨基苯甲酸修饰的磁性 Fe3O4 纳米粒子 [ @ABA-苯胺-CuI 纳米复合材料] 的表面，并通过以下方法研究了其在制备多种苯并噻唑硫化物芳基和杂芳基中的催化活性：以KOAc为碱，以PEG-400为溶剂，2-碘苯胺与二硫化碳、芳基或杂芳基碘化物的一锅三组分反应。TEM和SEM图像显示 @ABA-苯胺-CuI颗粒的形状为球形，颗粒尺寸约为12-25纳米。
• N-heterocyclic carbene copper(I) complex-catalyzed direct C–H thiolation of benzothiazoles
  作者：Hiroshi Inomata、Ayumi Toh、Takashi Mitsui、Shin-ichi Fukuzawa

  DOI：10.1016/j.tetlet.2013.06.104

  日期：2013.8

  N-heterocyclic carbene (NHC) copper(I) complexes based on imidazol-2-ylidene and 1,2,3-triazol-5-ylidene catalyzed the direct C-H thiolation of benzothiazoles and benzoxazoles with aryl and alkyl thiols to give 2-aryl and 2-alkylthiobenzothiazoles in moderate-to-good yields. The NHC copper(I) complex [(IPr)CuI] was the most effective catalyst for the reaction among the NHC-Cu(I) complexes examined in this study. (C) 2013 Elsevier Ltd. All rights reserved.
• 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.