5-methyl-2-(3-(trifluoromethyl)phenyl)benzo[d]oxazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-methyl-2-(3-(trifluoromethyl)phenyl)benzo[d]oxazole
• 英文别名: 5-Methyl-2-[3-(trifluoromethyl)phenyl]-1,3-benzoxazole；5-methyl-2-[3-(trifluoromethyl)phenyl]-1,3-benzoxazole
• 化学式: C₁₅H₁₀F₃NO
• 分子量: 277.246
• InChiKey: ZNCSEZIZWXXUDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-碘三氟甲苯 在 manganese(IV) oxide 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 copper(II) bis(trifluoromethanesulfonate) 、 三乙胺 作用下， 以 四氢呋喃 、 邻二甲苯 、 丙酮 为溶剂， 反应 19.0h， 生成 5-methyl-2-(3-(trifluoromethyl)phenyl)benzo[d]oxazole
  参考文献：
  名称：

  苯并恶唑的合成经由alkynones与2-氨基苯酚的铜催化加氢胺化

  摘要：

  我们在本文中描述了通过铜与2-氨基苯酚的炔属酮的铜催化加氢胺化来合成苯并恶唑衍生物的方法。该方法以高收率生产了多种官能化的苯并恶唑衍生物。初步的机理实验表明，该反应将通过铜催化的炔烃加氢胺化和β-亚氨基酮的连续分子内环化/铜催化剂促进的苯乙酮的消除而进行。

  DOI：

  10.1039/c9ob00572b

文献信息

• Nickel-Catalyzed Coupling of Azoles with Aromatic Nitriles
  作者：Mckenna G. Hanson、Noelle M. Olson、Zubaoyi Yi、Grace Wilson、Dipannita Kalyani

  DOI：10.1021/acs.orglett.7b01938

  日期：2017.8.18

  This manuscript describes the Ni-catalyzed coupling of azoles with aromatic nitriles. The use of BPh3 promotes these arylations with electronically diverse azoles and benzonitriles. While the nickel catalyst is necessary for the arylations of phenyl oxazoles, arylation of benzoxazoles with some nitriles affords the arylated products even in the absence of the Ni catalyst albeit in lower yield than

  该手稿描述了Ni催化的唑类化合物与芳族腈的偶联。BPh 3的使用可促进电子形式多样的唑和苄腈的这些芳基化。尽管镍催化剂对于苯基恶唑的芳基化是必需的，但是即使在不存在Ni催化剂的情况下，苯并恶唑与某些腈的芳基化也可以提供芳基化的产物，尽管收率比催化方法低。与未催化的转化相比，镍催化的方法显示出更高的速率和更广阔的范围。
• Ni-Catalyzed C–H Arylation of Oxazoles and Benzoxazoles Using Pharmaceutically Relevant Aryl Chlorides and Bromides
  作者：Helen Larson、Danielle Schultz、Dipannita Kalyani

  DOI：10.1021/acs.joc.9b02094

  日期：2019.10.18

  benzoxazoles with aryl halides. A series of aryl, heteroaryl, and druglike electrophiles relevant to pharmaceutical applications were surveyed. The desired arylated products were obtained in synthetically useful yields using electronically and structurally varied aryl halides. The use of microscale high-throughput experimentation was essential for both the rapid identification of optimal reaction parameters

  该手稿详细介绍了恶唑和苯并恶唑与芳基卤化物进行镍催化的芳基化反应的进展。调查了一系列与药物应用相关的芳基，杂芳基和类药物亲电试剂。使用电子和结构上变化的芳基卤化物以合成有用的产率获得所需的芳基化产物。微型高通量实验的使用对于快速确定最佳反应参数和研究芳基卤化物的范围都是必不可少的。
• DalPhos/Nickel-Catalyzed C2–H Arylation of 1,3-Azoles Using a Dual-Base System
  作者：Nicholas E. Bodé、Mark Stradiotto

  DOI：10.1021/acs.orglett.3c03393

  日期：2023.12.15

  orane/sodium trifluoroacetate (BTPP/NaTFA) “dual-base” system in combination with an air-stable Ni(II) precatalyst containing either CyPAd-DalPhos or PhPAd-DalPhos. These catalyst systems enable access to a reaction scope that encompasses a range of challenging oxidative addition partners, including (hetero)aryl chlorides as well as pivalates, tosylates, and other related phenol derivatives. The utility

  我们报告了一种用于（苯并）恶唑和（苯并）噻唑 C2 官能化的通用方法，采用叔丁基亚氨基三（吡咯烷）正膦/三氟乙酸钠（BTPP/NaTFA）“双碱”系统与空气稳定相结合含有 CyPAd-DalPhos 或 PhPAd-DalPhos 的 Ni(II) 预催化剂。这些催化剂系统能够实现涵盖一系列具有挑战性的氧化加成伙伴的反应范围，包括（杂）芳基氯以及新戊酸酯、甲苯磺酸酯和其他相关苯酚衍生物。通过活性药物成分的衍生化和噻唑衍生物的 5 mmol 合成证明了该方法的实用性。
• Nickel-catalyzed C−H arylation of benzoxazoles and oxazoles: Benchmarking the influence of electronic, steric and leaving group variations in phenolic electrophiles
  作者：Deborah F. Steinberg、Morgan C. Turk、Dipannita Kalyani

  DOI：10.1016/j.tet.2017.02.021

  日期：2017.4

  Electronic, steric and leaving group effects for Ni-catalyzed direct arylations using C-O electrophiles were benchmarked. The scope of arylations with pivalates was general with respect to both the electronics on the electrophile and the azoles. Furthermore, the arylation of azoles with tosylates, mesylates and carbamates with varying electronics was explored, and showed electronic trends similar to those of the pivalate reactions. Finally, the relative rate of arylation of 5-methyl benzoxazole with two electronically-similar electrophiles bearing different leaving groups was established. The results from these studies implicate the following order of relative reactivity: mesylates > pivalates > carbamates. (C) 2017 Elsevier Ltd. All rights reserved.
• Base-Promoted Formal Arylation of Benzo[<i>d</i>]oxazoles with Acyl Chloride
  作者：Lei Wang、Xinyi Ren、Jintao Yu、Yan Jiang、Jiang Cheng

  DOI：10.1021/jo402106q

  日期：2013.12.6

  A base-promoted formal arylation of benzo[d]-oxazoles with acyl chloride was achieved in moderate to good yields. This reaction was triggered by the N-acylation of oxazole to form an iminium intermediate. Then, the addition of H2O to the iminium formed the hemiacetal intermediate. After the sequential ring-opening, extrusion of CO, the ring closure, the dehydration delivered the formal arylation product. In comparison with the transition-metal-catalyzed methodology, it represents an alternative arylation method leading to 2-arylbenzooxazole.