3-phenylbenzo[d]thiazole-2(3H)-thione | 24097-02-7

• 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: 3-phenylbenzo[d]thiazole-2(3H)-thione
• 英文别名: 3-phenyl-3H-benzothiazole-2-thione；3-Phenylbenzothiazoline-2-thione；3-phenyl-1,3-benzothiazole-2-thione
• CAS: 24097-02-7
• 化学式: C₁₃H₉NS₂
• 分子量: 243.353
• InChiKey: DGQNHOUEAIUCKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  60.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-phenylbenzo[d]thiazole-2(3H)-thione 、 对甲苯磺酸甲酯 生成 2-methylsulfanyl-3-phenyl-benzothiazolium; toluene-4-sulfonate
  参考文献：
  名称：

  Color and Constitution. V.¹ The Absorption of Unsymmetrical Cyanines. Resonance as a Basis for a Classification of Dyes

  摘要：

  DOI：

  10.1021/ja01254a002
• 作为产物：
  描述：

  3-苯基苯并噻唑-2(3H)-酮 在 tetraphosphorus decasulfide 、 间二甲苯 作用下， 生成 3-phenylbenzo[d]thiazole-2(3H)-thione
  参考文献：
  名称：

  Color and Constitution. V.¹ The Absorption of Unsymmetrical Cyanines. Resonance as a Basis for a Classification of Dyes

  摘要：

  DOI：

  10.1021/ja01254a002

文献信息

• A catalyst-free and additive-free method for the synthesis of benzothiazolethiones from <i>o</i>-iodoanilines, DMSO and potassium sulfide
  作者：Xiaoming Zhu、Wenguang Li、Xiai Luo、Guobo Deng、Yun Liang、Jianbing Liu

  DOI：10.1039/c8gc00477c

  日期：——

  Under catalyst-free and additive-free conditions, a novel, convenient, environment-friendly method for the synthesis of benzothiazolethiones from o-iodoanilines, K₂S and DMSO has been developed.

  在无催化剂和添加剂的条件下，已开发了一种新颖、方便、环保的方法，用于从o-碘苯胺、K₂S和DMSO合成苯并噻唑硫醚。
• Cleaner and greener synthesis of 3<i>H</i>-benzothiazole-2-thione and its derivatives
  作者：Nitin Srivastava、Ram Kishore

  DOI：10.1080/17415993.2020.1803321

  日期：2021.1.2

  A cleaner and greener method of synthesis of 3H-benzothiazole-2-thione is being reported in this communication. In this method, various o-iodoaniline derivatives are reacted with carbon disulfide in the presence of Cs2CO3 and tetramethyl ammonium bromide (TMAB) to give 3H-benzothiazole-2-thione and its derivatives in higher yields. GRAPHICAL ABSTRACT

  本通讯报道了一种更清洁、更环保的 3H-苯并噻唑-2-硫酮合成方法。在该方法中，各种邻碘苯胺衍生物在 Cs2CO3 和四甲基溴化铵 (TMAB) 的存在下与二硫化碳反应，以更高的收率得到 3H-苯并噻唑-2-硫酮及其衍生物。图形概要
• Metal-Free Temperature-Controlled Intermolecular [3 + 2] Annulation to Access Benzo[<i>d</i>]thiazole-2(3<i>H</i>)-thiones and Benzo[<i>d</i>]thiazol-2(3<i>H</i>)-ones
  作者：Xiaoya Zhuo、Lvyin Zheng、Xiaoying Zou、Yumei Zhong、Wei Guo

  DOI：10.1021/acs.joc.2c01060

  日期：2022.8.5

  A facile access to benzo[d]thiazole-2(3H)-thiones and benzo[d]thiazol-2(3H)-ones has been developed through a temperature-controlled intermolecular [3 + 2] annulation of N,N-disubstituted arylhydrazines with CS2 in the presence of DMSO. This protocol can obviate the prefunctionalization of the starting materials. This direct C–S/C–N bond formation reaction was performed in the absence of any external

  通过温度控制的 N,N 分子间 [3 + 2] 环化，开发了一种容易获得苯并[ d ]噻唑-2(3 H )-硫酮和苯并[ d ]噻唑-2(3 H )-酮的方法-在DMSO存在下用CS 2二取代的芳基肼。该协议可以避免起始材料的预功能化。这种直接的 C-S/C-N 键形成反应是在没有任何外部催化剂、过渡金属、碱、配体和氧化剂的情况下进行的，具有高步骤经济性。
• Copper-Catalyzed Three-Component Synthesis of Benzothiazolethiones from <i>o</i>-Iodoanilines, Isocyanide, and Potassium Sulfide
  作者：Pan Dang、Weilan Zeng、Yun Liang

  DOI：10.1021/ol503186w

  日期：2015.1.2

  An efficient copper catalyzed strategy for the synthesis of a variety of benzothiazolethione derivatives has been developed. In the presence of CuCl, the three-component reaction of o-iodoanilines and K2S with p-toluenesulfonylmethyl isocyanide proceeded smoothly to obtain the corresponding benzothiazolethiones in good to excellent isolated yields. Notably, isocyanide functioned as a carbon source and K2S functioned as a sulfur source in this reaction.
• 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.