6-fluoro-2-(tetrahydrofuran-2-yl)benzo[d]thiazole | 1451260-73-3

• 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-2-(tetrahydrofuran-2-yl)benzo[d]thiazole
• 英文别名: Benzothiazole, 6-fluoro-2-(tetrahydro-2-furanyl)-；6-fluoro-2-(oxolan-2-yl)-1,3-benzothiazole
• CAS: 1451260-73-3
• 化学式: C₁₁H₁₀FNOS
• 分子量: 223.271
• InChiKey: QDCMHPUIQQYORH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 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：
  4

反应信息

• 作为产物：
  描述：

  6-氟-2-巯基苯并噻唑 在 oxone 、 TBADT 、 sodium hydride 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 36.5h， 生成 6-fluoro-2-(tetrahydrofuran-2-yl)benzo[d]thiazole
  参考文献：
  名称：

  N-杂芳烃与醛在水相中的光催化羟烷基化

  摘要：

  羟烷基化N -杂芳烃是广泛的生物活性天然分子中有趣的支架。在此，建立了一种光氧化还原催化的唑衍生物在空气气氛下在水相中与醛的羟烷基化方法。此外，我们的催化体系也适用于唑类衍生物与烷烃的烷基化反应。该方法具有生态友好、无需外加、官能团相容性好等特点。

  DOI：

  10.1039/d3gc00162h

文献信息

• Iron-catalyzed direct α-arylation of ethers with azoles
  作者：Arkaitz Correa、Béla Fiser、Enrique Gómez-Bengoa

  DOI：10.1039/c5cc05005g

  日期：——

  The direct α-arylation of cyclic and acyclic ethers with azoles has been achieved, which features a novel iron-catalyzed cross-dehydrogenative coupling (CDC) process.

  环状和非环状醚与唑类化合物的直接α-芳基化已经实现，其中包括一种新颖的铁催化的交叉脱氢偶联（CDC）过程。
• FeCl₃‐Catalyzed C(<i>sp</i>³)−H Heteroarylation Enabled by Photoinduced Ligand‐to‐Metal Charge Transfer
  作者：Pengcheng Li、Jia‐Lin Tu、Han Gao、Chengcheng Shi、Yining Zhu、Lin Guo、Chao Yang、Wujiong Xia

  DOI：10.1002/adsc.202301020

  日期：2024.1.30

  alkanes via synergistic visible light-driven redox reaction and FeCl3 catalysis. This transformation involves C−H activation by a chlorine radical generated during the iron-promoted ligand-to-metal charge transfer process, triggering subsequent C−H pyrimidination. The substrates and catalysts are inexpensive and readily available, while the reaction conditions and procedures are simple without the need

  在此，我们报告了一种通过协同可见光驱动的氧化还原反应和 FeCl 3催化进行惰性烷烃嘧啶化的策略。这种转变涉及铁促进的配体到金属电荷转移过程中产生的氯自由基对 CH 的活化，从而引发随后的 CH 嘧啶化。底物和催化剂廉价易得，反应条件和程序简单，不需要外部氧化剂。这项工作为合成具有高结构多样性的嘧啶衍生物提供了一种实用方法。
• 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.