6-chloro-2-(tetrahydrofuran-2-yl)benzo[d]thiazole | 1451260-74-4

• 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-chloro-2-(tetrahydrofuran-2-yl)benzo[d]thiazole
• 英文别名: Benzothiazole, 6-chloro-2-(tetrahydro-2-furanyl)-；6-chloro-2-(oxolan-2-yl)-1,3-benzothiazole
• CAS: 1451260-74-4
• 化学式: C₁₁H₁₀ClNOS
• 分子量: 239.725
• InChiKey: SCCKUVMZXYTFCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  50.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氨基-6-氯苯并噻唑 在 dipotassium peroxodisulfate 、 磷酸 、 copper(II) bis(trifluoromethanesulfonate) 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 14.0h， 生成 6-chloro-2-(tetrahydrofuran-2-yl)benzo[d]thiazole
  参考文献：
  名称：

  Cu-Catalyzed Cross-Dehydrogenative Coupling Reactions of (Benzo)thiazoles with Cyclic Ethers

  摘要：

  Copper-catalyzed cross-dehydrogenative coupling (CDC) reactions of (benzo)thiazoles with cyclic ethers were developed under mild conditions. In particular, the formation of C-C bonds via the CDC reactions between non-benzo-fused azoles and ethers are reported for the first time. In addition, the acetals, known as the masked 2-thiazolecarboxaldehydes, could be successfully obtained by this CDC reaction. The preliminary mechanism and supportive DFT calculations are discussed as well.

  DOI：

  10.1021/ol4022113

文献信息

• Visible Light‐Induced Metal‐Free and Oxidant‐Free Radical Cyclization of (2‐Isocyanoaryl)(methyl)sulfanes with Ethers
  作者：Xiao‐Yu Xie、Yang Li、Yun‐Tao Xia、Kai Luo、Lei Wu

  DOI：10.1002/ejoc.202100501

  日期：2021.8.13

  AbstractA novel cascade cyclization of (2‐isocyanoaryl) (methyl)sulfanes and ethers is developed. With 4CzIPN as a photocatalyst and the irradiation of blue LED light, ether radicals are efficiently generated without adding any oxidant, endowing the strategy with features of oxidant‐free, metal‐free, mild reaction conditions, and operational simplicity. This strategy provides efficient approach to access various ether‐containing benzothiazoles in acceptable to good yields.
• Cu-Catalyzed Cross-Dehydrogenative Coupling Reactions of (Benzo)thiazoles with Cyclic Ethers
  作者：Zengyang Xie、Yuping Cai、Hongwen Hu、Chen Lin、Juli Jiang、Zhaoxu Chen、Leyong Wang、Yi Pan

  DOI：10.1021/ol4022113

  日期：2013.9.6

  Copper-catalyzed cross-dehydrogenative coupling (CDC) reactions of (benzo)thiazoles with cyclic ethers were developed under mild conditions. In particular, the formation of C-C bonds via the CDC reactions between non-benzo-fused azoles and ethers are reported for the first time. In addition, the acetals, known as the masked 2-thiazolecarboxaldehydes, could be successfully obtained by this CDC reaction. The preliminary mechanism and supportive DFT calculations are discussed as well.