6-fluoro-3-methyl-1,3-benzothiazole-2(3H)-thione | 24097-04-9

• 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: 6-fluoro-3-methyl-1,3-benzothiazole-2(3H)-thione
• 英文别名: 6-fluoro-3-methylbenzo[d]thiazole-2(3H)-thione；6-fluoro-3-methyl-3H-benzothiazole-2-thione；3-Methyl-6-fluoro-2-benzothiazolthion；6-Fluoro-3-methyl-1,3-benzothiazole-2-thione
• CAS: 24097-04-9
• 化学式: C₈H₆FNS₂
• 分子量: 199.273
• InChiKey: KYGDJMKTITZLBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  60.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-碘-4-氟苯胺 在 potassium sulfide 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 6-fluoro-3-methyl-1,3-benzothiazole-2(3H)-thione
  参考文献：
  名称：

  A catalyst-free and additive-free method for the synthesis of benzothiazolethiones from o-iodoanilines, DMSO and potassium sulfide

  摘要：

  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。

  DOI：

  10.1039/c8gc00477c

文献信息

• Ortho-Selective Nucleophilic Aromatic Substitution Reactions of Polyhaloanilines with Potassium/Sodium <i>O</i>-Ethyl Xanthate:  A Convenient Access to Halogenated 2(3<i>H</i>)-Benzothiazolethiones
  作者：Lei Zhu、Mingbao Zhang

  DOI：10.1021/jo049056s

  日期：2004.10.1

  Polyhaloanilines bearing an ortho halogen atom undergo smooth nucleophilic aromatic substitution reactions with anionic sulfur nucleophiles at relatively mild temperatures (95−120 °C). These reactions are very efficient and highly ortho-selective. With potassium/sodium O-ethyl xanthate as a nucleophile, subsequent cyclization follows to afford halogenated 2(3H)-benzothiazolethiones (2-mercaptobenzothiazoles)

  带有邻卤原子的聚卤苯胺在相对温和的温度下（95-120°C）与阴离子硫亲核试剂进行平滑的亲核芳族取代反应。这些反应非常有效且具有高邻位选择性。以O-乙基黄原酸钾/钠为亲核试剂，随后的环化反应以高收率提供卤代的2（3 H）-苯并噻唑硫酮（2-巯基苯并噻唑）。
• 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.