2-(2,6-difluorophenyl)benzo[d]thiazole | 152993-87-8

• 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-(2,6-difluorophenyl)benzo[d]thiazole
• 英文别名: 2-(2,6-Difluorophenyl)-1,3-benzothiazole
• CAS: 152993-87-8
• 化学式: C₁₃H₇F₂NS
• 分子量: 247.268
• InChiKey: OHZGIOLGRPKMGJ-UHFFFAOYSA-N

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

• 作为产物：
  描述：

  2-苯基苯并噻唑 在 四(三苯基膦)钯 、 N-氟代双苯磺酰胺 、 L-脯氨酸 作用下， 以 环己烷 为溶剂， 反应 10.0h， 生成 2-(2,6-difluorophenyl)benzo[d]thiazole
  参考文献：
  名称：

  Pd(PPh3)4-catalyzed direct ortho-fluorination of 2-arylbenzothiazoles with an electrophilic fluoride N-fluorobenzenesulfonimide (NFSI)

  摘要：

  An efficient protocol was developed for regio-selective Pd-catalyzed direct ortho-fluorination of 2-alylbenzo[d]thiazoles using N-fluorobenzenesulfonimide (NFSI) as the F+ source, and L-proline as the crucial promoter. The present method offered a practical route to synthesize valuable fluorinated products, which are of potential importance in the pharmaceutical and agrochemical industries. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.11.034

文献信息

• Cobalt-Catalyzed Decarboxylative C–H (Hetero)Arylation for the Synthesis of Arylheteroarenes and Unsymmetrical Biheteroaryls
  作者：Yanrong Li、Fen Qian、Mengshi Wang、Hongjian Lu、Guigen Li

  DOI：10.1021/acs.orglett.7b02730

  日期：2017.10.20

  benzothiazoles or benzoxazoles is reported. This represents a first example of metal-catalyzed decarboxylative C–H heteroarylation of benzo-fused heterocycles. The transformation provides a convenient route, with good yields and functional group tolerance, to various important arylheteroaryl and unsymmetrical biheteroaryl structural motifs.

  报道了（杂）芳基羧酸与苯并噻唑或苯并恶唑的钴催化的脱羧交叉偶联反应。这代表了金属催化的苯并稠合杂环的脱羧CH杂杂芳基化反应的第一个例子。该转化为各种重要的芳基杂芳基和不对称的双杂芳基结构基序提供了一条方便的途径，具有良好的收率和官能团耐受性。
• Pd-Catalyzed Decarboxylative Arylation of Thiazole, Benzoxazole, and Polyfluorobenzene with Substituted Benzoic Acids
  作者：Kai Xie、Zhiyong Yang、Xingjian Zhou、Xiujian Li、Sizhuo Wang、Ze Tan、Xiangyu An、Can-Cheng Guo

  DOI：10.1021/ol100296b

  日期：2010.4.2

  with various substituted benzoic acids is developed. The reaction is compatible with both electron-rich and electron-poor benzoic acids. It can also be extended to the synthesis of polyfluoro-substituted biaryls using polyfluorobenzenes as the starting materials.

  建立了Pd催化的噻唑和苯并恶唑与各种取代的苯甲酸的脱羧偶联反应。该反应与富电子和贫电子的苯甲酸都相容。它也可以扩展到以多氟苯为原料合成多氟取代的联芳基。
• Synthesis of some benzothiazoles by developing a new protocol using urea nitrate as a catalyst and their antimicrobial activities
  作者：Parvin Kumar、Rimpy Bhatia、Radhika Khanna、Aarti Dalal、Dinesh Kumar、Parveen Surain、Ramesh C. Kamboj

  DOI：10.1080/17415993.2017.1334781

  日期：——

  ABSTRACT The present communication demonstrates the development of urea nitrate as an effective and efficient catalyst for the synthesis of some 2-substituted benzothiazoles. Instant progress of reaction at room temperature under solvent-free condition, very high catalytic activity, inexpensive, clean reaction profile, operational simplicity, large-scale synthesis and appreciable yields are the main

  摘要 本通讯展示了硝酸尿素作为合成一些 2-取代苯并噻唑的有效催化剂的发展。该协议的主要优点是室温下无溶剂条件下反应的即时进展、非常高的催化活性、廉价、清洁的反应曲线、操作简单、大规模合成和可观的产率。已经评估了这些合成的苯并噻唑对革兰氏阳性菌（枯草芽孢杆菌 MTCC 121）的抗菌和抗真菌活性；两种革兰氏阴性菌（大肠杆菌 MTCC 1652 和铜绿假单胞菌 MTCC 741）和两种真菌（白色念珠菌 MTCC 3017 和酿酒酵母 MTCC 170）。发现化合物 3n 对所有测试微生物的活性最强。图形概要
• Methanesulfonic Acid/SiO₂ as an Efficient Combination for the Synthesis of 2-Substituted Aromatic and Aliphatic Benzothiazoles from Carboxylic Acids
  作者：Hashem Sharghi、Omid Asemani

  DOI：10.1080/00397910802431214

  日期：2009.2.9

  Methanesulfonic acid/SiO2 (1 mL/0.3 g) was found to be as an expeditious mixture in the synthesis of 2-substituted aromatic and aliphatic benzothiazoles at 140 °C using carboxylic acids. After a simple workup, benzothiazoles were obtained in good yields. Simplicity, use of widely available and diverse carboxylic acids, and easy handling of the reaction conditions are among the benefits of the method.

  摘要 甲磺酸/SiO2 (1 mL/0.3 g) 被发现是在 140 °C 下使用羧酸合成 2-取代芳香族和脂肪族苯并噻唑的快速混合物。经过简单的处理后，苯并噻唑以良好的收率获得。该方法的优点包括简单、使用广泛可用的多种羧酸以及易于处理反应条件。
• Magnetic nanoparticles-supported tungstosilicic acid: as an efficient magnetically separable solid acid for the synthesis of benzoazoles in water
  作者：Ali Khalafi-Nezhad、Farhad Panahi、Reza Yousefi、Sina Sarrafi、Yasaman Gholamalipour

  DOI：10.1007/s13738-013-0400-8

  日期：2014.10

  The magnetic nanoparticles-supported tungstosilicic acid (TSAMNP) was found to be a highly efficient solid acid for the synthesis of benzoazoles in water. TSAMNP catalyst was achieved by the immobilization of tungstosilicic acid [H4(W12SiO40)] species on the silica core–shell magnetic nanoparticles (Fe3O4@SiO2). A variety of aldehydes were successfully condensed with 1,2-diaminobenzene, 2-aminophenol and 2-aminothiophenol in water as a green solvent to synthesize benzoazoles in good-to-excellent yields. TSAMNP catalyst was easily separated from the reaction mixture and reused several times without any loss of efficiency.

  磁性纳米粒子支持的钨硅酸（TSAMNP）被发现是一种高效的固体酸，用于在水中合成苯并噁唑。TSAMNP催化剂是通过将钨硅酸[H4(W12SiO40)]物种固定在硅核壳磁性纳米粒子（Fe3O4@SiO2）上实现的。多种醛类与1,2-二氨基苯、2-氨基酚和2-氨基硫代苯酚在水这一绿色溶剂中成功缩合，合成了苯并噁唑，产率良好到优异。TSAMNP催化剂能够轻松从反应混合物中分离，并在多次重复使用中没有效率损失。