2-(2-(trifluoromethyl)phenyl)benzo[d]thiazole | 156215-39-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(2-(trifluoromethyl)phenyl)benzo[d]thiazole
• 英文别名: 2-(2'-trifluoromethylphenyl)benzothiazole；2-(2-trifluoromethylphenyl)benzothiazole；2-[2-(Trifluoromethyl)phenyl]-1,3-benzothiazole
• CAS: 156215-39-3
• 化学式: C₁₄H₈F₃NS
• 分子量: 279.285
• InChiKey: PWMCQSYGJVJXFU-UHFFFAOYSA-N

物化性质

• 熔点：
  132-134 °C
• 沸点：
  368.0±52.0 °C(Predicted)
• 密度：
  1.362±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  41.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  iridium(III) chloride trihydrate 、 2-(2-(trifluoromethyl)phenyl)benzo[d]thiazole 以 乙二醇乙醚 、 水 为溶剂， 反应 24.0h， 生成 C₅₆H₂₈Cl₂F₁₂Ir₂N₄S₄
  参考文献：
  名称：

  Inkable CF3-functionalized benzothiazole/benzimidazole-Ir(III) complexes for efficient bilayer-inkjet-printed OLEDs

  摘要：

  DOI：

  10.1016/j.jorganchem.2021.122157
• 作为产物：
  描述：

  邻三氟甲基苯甲醛 、 2-氨基苯硫醇 在 mesoporous mixed metal oxide nanocrystals of Al₂O₃-Fe₂O₃, Al₂O₃-V₂O₅, Al₂O₃-CuO 作用下， 反应 0.02h， 以89%的产率得到2-(2-(trifluoromethyl)phenyl)benzo[d]thiazole
  参考文献：
  名称：

  Mesoporous mixed metal oxide nanocrystals: Efficient and recyclable heterogeneous catalysts for the synthesis of 1,2-disubstituted benzimidazoles and 2-substituted benzothiazoles

  摘要：

  Present communication elicits the use of mesoporous mixed metal oxide nanocrystals of Al2O3-Fe2O3. Al2O3-V2O5 and Al2O3-CuO as heterogeneous catalysts for the preparation of series of medicinally significant 1,2-disubstituted benzimidazoles and 2-substituted benzothiazoles. These nanocrystalline catalysts exhibited remarkable catalytic activity with a high substrate to catalyst weight ratio (20:1) to achieve the synthetic targets in the range of yield 81-96%. The solvent-free microwave assisted synthesis of these compounds was an advantageous way which resulted in excellent yields in much lesser time (0.75-1.5 min) in comparison to conventional heating. The use of catalyst in eco-friendly green protocol and its reusability up to four cycles with similar catalytic response are the unique features of the heterogeneous catalysis. This protocol provided greater selectivity, cost-efficiency, clean reaction profiles, simple work-up procedure and high yields. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2011.03.027

文献信息

• Nickel-Catalyzed CH Arylation of Azoles with Haloarenes: Scope, Mechanism, and Applications to the Synthesis of Bioactive Molecules
  作者：Takuya Yamamoto、Kei Muto、Masato Komiyama、Jérôme Canivet、Junichiro Yamaguchi、Kenichiro Itami

  DOI：10.1002/chem.201101091

  日期：2011.8.29

  Novel nickel‐based catalytic systems for the CH arylation of azoles with haloarenes and aryl triflates have been developed. We have established that Ni(OAc)2/bipy/LiOtBu serves as a general catalytic system for the coupling with aryl bromides and iodides as aryl electrophiles. For couplings with more challenging electrophiles, such as aryl chlorides and triflates, the Ni(OAc)2/dppf (dppf=1,1′‐bis

  对于C新颖的镍基催化体系与卤代芳烃和芳基三氟甲磺酸酯唑h的芳基化得到了发展。我们已经确定，Ni（OAc）2 / bipy / LiO t Bu用作与芳基溴化物和碘化物作为芳基亲电子试剂偶联的一般催化体系。对于与更具挑战性的亲电试剂（例如芳基氯化物和三氟甲磺酸酯）偶联，发现Ni（OAc）2 / dppf（dppf = 1,1'-bis（diphenylphosphino）ferrocene）系统是有效的。噻唑，苯并噻唑，恶唑，苯并恶唑和苯并咪唑可用作杂芳烃偶联伴侣。经过进一步研究，我们发现了使用Mg（O t Bu）2进行本偶联的新方案作为LiO t Bu的温和且便宜的替代品。还描述了试图揭示这种镍催化的杂联芳基偶联机理的尝试。该新开发的方法已成功应用于非布索坦（一种有效治疗痛风和高尿酸血症的黄嘌呤氧化酶抑制剂），他法米第（一种有效治疗TTR淀粉样蛋白多神经病的药物）和texaline（一种天然的抗结核药物）的合成活动）。
• [EN] FUSED HETEROCYCLIC DERIVATIVES AS PPAR MODULATORS<br/>[FR] DERIVES HETEROCYCLIQUES FUSIONNES UTILISES EN TANT QUE MODULATEURS PPAR
  申请人：LILLY CO ELI

  公开号：WO2004063155A1

  公开（公告）日：2004-07-29

  The present invention is directed to compounds represented by the following structural formula, Formula I: wherein (a) X is selected from the group consisting of a single bond, O, S. S(O)2 and N; (b) U is an aliphatic linker; (c) Y is selected from the group consisting of C, O, S, NH and a single bond; (d) E is C(R3) (R4)A or A and wherein (i) A is selected from the group consisting of carboxyl, tetrazole, C1-C6 alkylnitrile, carboxamidek, sulfonamide and acylsulfonamide; (e) B is selected from the group consisting of S, O, C, and N; (f) Z is selected from the group consisting of N and C; with the proviso that when B is C then Z is N.

  本发明涉及由以下结构式I表示的化合物：其中（a）X选自单键、O、S、S（O）2和N组成的群；（b）U是脂肪链连接物；（c）Y选自C、O、S、NH和单键组成的群；（d）E是C（R3）（R4）A或A，其中（i）A选自羧基、四唑基、C1-C6烷基腈、羧酰胺、磺酰胺和酰基磺酰胺组成的群；（e）B选自S、O、C和N组成的群；（f）Z选自N和C组成的群；但当B为C时，则Z为N。
• Graphene oxide-catalyzed synthesis of benzothiazoles with amines and elemental sulfur via oxidative coupling strategy of amines to imines
  作者：Haiping He、Dehao Duan、Hong Li、Yifei Wei、Liang Nie、Bo Tang、Hanyu Wang、Xiaowei Han、Panpan Huang、Xiangjun Peng

  DOI：10.1016/j.tet.2021.132624

  日期：2022.1

  The graphene oxide-catalyzed coupling and cyclization reactions of primary amines with elemental sulfur was developed to afford various optically property benzothiazoles. This coupling and cyclization strategies proceeded under the oxidant system graphene oxide/O2 and constructed carbon-heteroatom (N, S) bonds with amines and elemental sulfur. Due to benzothiazoles as common chromophores, these products

  开发了氧化石墨烯催化的伯胺与元素硫的偶联和环化反应，以提供各种光学性质的苯并噻唑。这种偶联和环化策略在氧化剂体系氧化石墨烯/O 2下进行，并与胺和元素硫构建了碳-杂原子（N，S）键。由于苯并噻唑是常见的发色团，这些产品表现出有趣的荧光特性，包括出色的斯托克斯位移（高达 161 nm）和量子产率（高达 74%）。利用产品在不同溶剂中的独特荧光响应，β-萘噻唑4a在 1,2-二氯乙烷中表现出优异的聚集诱导发射特性，是四氢呋喃中的 60 倍。
• Compounds
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：US10207985B2

  公开（公告）日：2019-02-19

  Compounds of the formula in which the substituents are as defined in claim 1, are suitable for use as nematicides.

  权利要求 1 所定义的式中取代基的化合物适合用作杀线虫剂。
• 10.1007/s10562-024-04707-w
  作者：Yu, Xiaofeng、Tian, Ruixin、Shi, Chunjie、Song, Renyuan、Wei, Zhengyou

  DOI：10.1007/s10562-024-04707-w

  日期：——

  commercially accessible nickel catalysts facilitate the synthesis of 2-arylbenzothiazoles from various aryllithium compounds and 2-chlorobenzothiazole. This catalytic process is effective irrespective of the presence of electron-withdrawing or electron-donating groups on the benzene ring of aryllithium. Among these zero-valent, divalent nickel, and divalent nickel complexes, divalent nickel complexes have the

  在 Kumada 反应中，市售的镍催化剂有助于从各种芳基锂化合物和 2-氯苯并噻唑合成 2-芳基苯并噻唑。无论芳基锂的苯环上是否存在吸电子基团或给电子基团，该催化过程都是有效的。在这些零价、二价镍和二价镍配合物中，二价镍配合物的催化效果最好。 NiCl 2 (PCy 3 ) 2 (Cy = 环己基) 具有最好的催化性能。由C 6 H 4 Li和2-氯苯并吡唑合成2-C 6 H 4 苯并吡唑的最高产率为92.1%。使用 NiCl 2 (PCy 3 ) 2 催化剂。该方法无需合成昂贵的钯试剂和镍络合物。  图形概要