2-(3,5-difluorophenyl)benzo[d]thiazole | 156215-40-6

• 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: 2-(3,5-difluorophenyl)benzo[d]thiazole
• 英文别名: 2-(3',5'-difluorophenyl)benzothiazole；2-(3,5-Difluorophenyl)-1,3-benzothiazole
• CAS: 156215-40-6
• 化学式: C₁₃H₇F₂NS
• 分子量: 247.268
• InChiKey: OGYOVVLJBWGWNX-UHFFFAOYSA-N

物化性质

• 沸点：
  358.7±52.0 °C(Predicted)
• 密度：
  1.373±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  17
• 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：
  41.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-溴苯腈 、 2-(3,5-difluorophenyl)benzo[d]thiazole 在 三甲基乙酸钾 、 palladium dichloride 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 16.0h， 以69%的产率得到
  参考文献：
  名称：

  带有苯并恶唑或苯并噻唑的二氟苯和二氯苯的钯催化无定向CH键芳基化

  摘要：

  在本文中，我们报道了钯催化带有苯并恶唑或苯并噻唑部分的二氟苯和二氯苯的直接芳基化，它们不充当引导基团。在芳基溴化物上具有适度的吸电子取代基作为偶联伙伴的情况下，使用无膦的PdCl 2催化剂和新戊酸钾/二甲基乙酰胺钾（PivOK / DMA）作为催化体系，反应可以顺利进行。该反应是区域选择性的，发生在氟或氯原子受阻较小的邻位。

  DOI：

  10.1016/j.catcom.2015.07.025
• 作为产物：
  描述：

  3,5-二氟苯甲醛 、 2-氨基苯硫醇 在 cerium(IV) oxide 作用下， 以 水 为溶剂， 反应 0.33h， 以76%的产率得到2-(3,5-difluorophenyl)benzo[d]thiazole
  参考文献：
  名称：

  Nano ceria catalyzed synthesis of substituted benzimidazole, benzothiazole, and benzoxazole in aqueous media

  摘要：

  A series of substituted benzimidazoles, benzothiazoles, and benzoxazoles was synthesized by combining 1,2-phenylenediamine, 2-aminothiophenol, or 2-aminophenol with aryl, heteroaryl, aliphatic, alpha,beta-unsaturated aldehydes in the presence of nano ceria (CeO2) as an efficient heterogeneous catalyst. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.09.092

文献信息

• Phosphine free Mn-complex catalysed dehydrogenative C–C and C–heteroatom bond formation: a sustainable approach to synthesize quinoxaline, pyrazine, benzothiazole and quinoline derivatives
  作者：Kalicharan Das、Avijit Mondal、Dipankar Srimani

  DOI：10.1039/c8cc05877f

  日期：——

  Herein the first sustainable synthesis of quinoxalines, pyrazines and benzothiazoles catalysed by a phosphine free Mn(I) complex via acceptorless dehydrogenative coupling (ADC) is reported. This method is also applied successfully to synthesize quinolines via the dehydrogenation (removal of H2) and condensation (removal of H2O) reaction between 2-aminobenzyl alcohols and secondary alcohols.

  本文报道了无膦的Mn（I）配合物通过无受体脱氢偶联（ADC）催化的喹喔啉，吡嗪和苯并噻唑的首次可持续合成。该方法也成功地应用于合成喹啉经由脱氢（脱H 2）和缩合（脱H 2 O）2 -氨基苄醇和仲醇之间的反应。
• Oxidant/Solvent-Controlled I₂-Catalyzed Domino Annulation for Selective Synthesis of 2-Aroylbenzothiazoles and 2-Arylbenzothiazoles under Metal-Free Conditions
  作者：Renchao Ma、Yuxin Ding、Rener Chen、Zhiming Wang、Lei Wang、Yongmin Ma

  DOI：10.1021/acs.joc.0c02095

  日期：2021.1.1

  A simple and practical domino protocol for the selective synthesis of 2-aroylbenzothiazoles and 2-aryl benzothiazoles catalyzed by I2 is developed under metal-free conditions. The reaction outcomes are exclusively controlled by the reaction oxidant/medium. With DMSO employed as both the solvent and the oxidant, an oxidation of aromatic methyl ketones takes precedence over the condensation with 2-aminobenzenethiols

  在无金属条件下开发了一种简单实用的多米诺协议，该协议可选择性合成I 2催化的2-芳酰基苯并噻唑和2-芳基苯并噻唑。反应结果完全由反应氧化剂/介质控制。在同时使用DMSO作为溶剂和氧化剂的情况下，芳族甲基酮的氧化作用优先于与2-氨基苯硫醇的缩合反应。另一方面，当反应在PhNO 2或含PhNO 2的1,4-二恶烷中进行时，芳族甲基酮与2-氨基苯硫醇的缩合反应优先形成亚胺，随后甲基被氧化由酮得到2-芳基苯并噻唑的唯一产物。PhNO 2 / I2首次提出共催化体系。
• Mettey, Yvette; Michaud, Sabine; Vierfond, Jean Michel, Heterocycles, 1994, vol. 38, # 5, p. 1001 - 1006
  作者：Mettey, Yvette、Michaud, Sabine、Vierfond, Jean Michel

  DOI：——

  日期：——
• THERMALLY ACTIVATED DELAYED FLUORESCENCE CHROMOPHORES AND ORGANIC LAYERS INCLUDING THE SAME
  申请人：Wright State University

  公开号：US20200131436A1

  公开（公告）日：2020-04-30

  Thermally activated delayed fluorescence chromophores may comprise a donor ligand, an acceptor ligand, and an acceptor tuner ligand. The donor ligand may be selected from one or more of carbazole, diphenylamine, phenothiazine, phenoxazine, or acridine. The acceptor ligand may be selected from one or more of benzoxazole, benzothiazole, or diphenyl sulfone. The acceptor tuner ligand may comprise a benzene ring. The benzene ring may be at least partially substituted. Organic layers, such as polymers or films, comprising the thermally activated delayed fluorescence chromophores are also disclosed.
• Nano ceria catalyzed synthesis of substituted benzimidazole, benzothiazole, and benzoxazole in aqueous media
  作者：Radheshyam Shelkar、Sachin Sarode、Jayashree Nagarkar

  DOI：10.1016/j.tetlet.2013.09.092

  日期：2013.12

  A series of substituted benzimidazoles, benzothiazoles, and benzoxazoles was synthesized by combining 1,2-phenylenediamine, 2-aminothiophenol, or 2-aminophenol with aryl, heteroaryl, aliphatic, alpha,beta-unsaturated aldehydes in the presence of nano ceria (CeO2) as an efficient heterogeneous catalyst. (C) 2013 Elsevier Ltd. All rights reserved.