(5-chlorobenzo[d]thiazol-2-yl)(4-fluorophenyl)methanone | 1268700-01-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5-chlorobenzo[d]thiazol-2-yl)(4-fluorophenyl)methanone
• 英文别名: (5-Chloro-1,3-benzothiazol-2-yl)-(4-fluorophenyl)methanone
• CAS: 1268700-01-1
• 化学式: C₁₄H₇ClFNOS
• 分子量: 291.733
• InChiKey: AOECMQKIYLKJGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-氯苯并噻唑 、 对氟甲苯 在 Selectfluor 、 三氟乙酸 作用下， 以 乙腈 为溶剂， 反应 10.0h， 以45%的产率得到(5-chlorobenzo[d]thiazol-2-yl)(4-fluorophenyl)methanone
  参考文献：
  名称：

  C2-arylacylation of 2H-benzothiazoles with methyl arenes via Selectfluor oxidation

  摘要：

  DOI：

  10.1016/j.tetlet.2021.153184

文献信息

• RuCl3·3H2O Catalyzed Tandem Reaction of Alkynylbromides with 2-Aminothiophenols in Water: A Convenient Synthesis of 2-Benzoylbenzothiazoles
  作者：Xuesen Fan、Yan He、Shenghai Guo、Xinying Zhang

  DOI：10.1071/ch11217

  日期：——

  RuCl3·3H2O catalyzed tandem reaction of alkynyl bromides with 2-aminothiophenols mediated by water is shown to represent a convenient synthesis of 2-benzoylbenzothiazoles. In addition, the Ru(iii) catalyst could be readily recovered and efficiently reused together with water up to three times.

  RuCl 3 ·3H 2 O催化炔基溴与水介导的2-氨基硫酚的串联反应表明可以方便地合成2-苯甲酰基苯并噻唑。另外，Ru（iii）催化剂可以容易地回收并与水一起有效地重复使用多达三遍。
• A Multipathway Coupled Domino Strategy: Metal-free Oxidative Cyclization for One-Pot Synthesis of 2-Acylbenzothiazoles from Multiform Substrates
  作者：Yan-ping Zhu、Feng-cheng Jia、Mei-cai Liu、An-xin Wu

  DOI：10.1021/ol301921t

  日期：2012.9.7

  A multipathway coupled domino strategy has been developed for the efficient synthesis of 2-acylbenzothiazoles from multiform substrates arylethenes, arylacetylenes, 2-hydroxy-aromatic ketones, and carbinols via four distinct pathways. Through a logical coupled oxidation/heterocyclization domino process, a variety of 2-acylbenzothiazoles were synthesized free of metal in one pot.

  已经开发了一种多途径偶联多米诺骨牌策略，用于通过多种不同的途径从多种形式的底物芳烃，芳基乙炔，2-羟基-芳族酮和甲醇中高效合成2-酰基苯并噻唑。通过逻辑耦合的氧化/杂环多米诺工艺，可以在一锅中合成多种不含金属的2-酰基苯并噻唑。
• 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。
• A Sustainable Synthesis of 2-Benzoxazyl and 2-Benzothiazyl Ketones from Alkynyl Bromides and 2-Amino(thio)phenols Promoted by a Recyclable Catalytic System
  作者：Liangyan Cui、Yan He、Xuesen Fan

  DOI：10.1002/cjoc.201100472

  日期：2012.4

  An environmentally and economically sustainable synthesis of 2‐benzoxazyl ketones and 2‐benzothiazyl ketones through FeCl3·6H2O catalyzed tandem reactions of alkynyl bromides with 2‐amino(thio)phenols in [bmim]BF4 has been developed. Remarkable advantages of this new synthetic strategy include high efficiency, readily available starting materials, and recyclable catalyst and reaction medium.

  通过FeCl 3 ·6H 2 O催化炔基溴化物与2-氨基（硫代）苯酚在[bmim] BF 4中的串联反应，在环境和经济上可持续地合成2-苯并恶唑酮和2-苯并噻唑酮。这种新的合成策略的显着优势包括高效，易于获得的原料以及可循环使用的催化剂和反应介质。
• A Novel PIFA/KOH Promoted Approach to Synthesize C2-arylacylated Benzothiazoles as Potential Drug Scaffolds
  作者：Xiao-Tong Sun、Zhi-Gang Hu、Zhen Huang、Ling-Li Zhou、Jian-Quan Weng

  DOI：10.3390/molecules27030726

  日期：——

  To discover an efficient and convenient method to synthesize C2-arylacylated benzothiazoles as potential drug scaffolds, a novel [bis(trifluoroacetoxy)iodo]benzene(PIFA)/KOH synergistically promoted direct ring-opening C2-arylacylation reaction of 2H-benzothiazoles with aryl methyl ketones has been developed. Various substrates were tolerated under optimized conditions affording the C2-arylacylation

  为了找到一种高效、便捷的合成C2-芳酰基化苯并噻唑作为潜在药物支架的方法，一种新型的[双(三氟乙酰氧基)碘]苯(PIFA)/KOH协同促进2H-苯并噻唑与芳基甲基的直接开环C2-芳基酰化反应酮已被开发出来。在优化条件下，各种底物均具有耐受性，38 个示例的 C2-芳基酰化产物产率为 70-95%。基于一系列受控实验，还提出了一种合理的机制。