4-(5-methylbenzo[d]oxazol-2-yl)benzonitrile | 920145-51-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(5-methylbenzo[d]oxazol-2-yl)benzonitrile
• 英文别名: 2-(4-cyanophenyl)-5-methyl-1,3-benzoxazole；4-(5-methyl-1,3-benzoxazol-2-yl)benzonitrile；5-methyl-2-(4-cyanophenyl)benzoxazole
• CAS: 920145-51-3
• 化学式: C₁₅H₁₀N₂O
• 分子量: 234.257
• InChiKey: AFVSAHGEUHZJIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 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：
  49.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-(3-hydroxy-3-phenylprop-1-yn-1-yl)benzonitrile 在 manganese(IV) oxide 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 邻二甲苯 、 丙酮 为溶剂， 反应 19.0h， 生成 4-(5-methylbenzo[d]oxazol-2-yl)benzonitrile
  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

• 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。
• Palladium(II) Immobilized Onto the Glucose Functionalized Magnetic Nanoparticle as a New and Efficient Catalyst for the One-pot Synthesis of Benzoxazoles
  作者：Firouz Matloubi Moghaddam、Vahid Saberi、Sepideh Kalhor、Nazila Veisi

  DOI：10.1002/aoc.4240

  日期：2018.4

  Palladium(II) have been immobilized into the nano magnetic Fe3O4 which was functionalized with glucose in order to achieve a one‐pot synthesis of 2‐substituted benzoxazole derivatives with high yields in the diverse range of organic solvents. The nano catalyst is highly dispersive in polar solvents and can be easily recovered and reused for 6 runs without significant loss of its activity. Finally,

  钯（II）已被固定在纳米磁性的Fe 3 O 4中，并用葡萄糖对其进行了功能化，以便在各种有机溶剂中以高收率一次合成2取代的苯并恶唑衍生物。纳米催化剂在极性溶剂中具有高度分散性，可以轻松回收并重复使用6次，而不会显着降低其活性。最后，通过FT-IR，TGA，CHN，SEM，EDX和原子吸收光谱对催化剂进行了全面表征。
• A one-pot, two-step microwave-assisted synthesis of highly functionalized benzoxazoles using solid-supported reagents (SSRs)
  作者：Marco Radi、Sara Saletti、Maurizio Botta

  DOI：10.1016/j.tetlet.2008.05.059

  日期：2008.7

  A one-pot, two-step protocol for the microwave-assisted solid-phase synthesis of substituted benzoxazoles has been developed starting from different polymer-bound esters we previously designed as solid-supported reagents (SSRs) for the acylation of amines, alcohols and phenols. The combination of a parallel synthesizer and a microwave reactor allowed to quickly prepare a collection of substituted benzoxaxoles

  已开发了一锅，两步的微波辅助固相合成取代苯并恶唑的规程，它是从我们先前设计为胺，醇和胺的酰化的固载试剂（SSR）的不同聚合物结合的酯开始的。酚类。平行合成器和微波反应器的组合可以快速制备高纯度和令人满意的收率的取代苯并恶唑的集合。该协议适用于自动化，可用于药物发现程序中组合库的制备。
• Compounds, Compositions and Methods for Stabilizing Transthyretin and Inhibiting Transthyretin Misfolding
  申请人：Labaudinière Richard

  公开号：US20110092545A1

  公开（公告）日：2011-04-21

  Compounds, compositions and methods are provided for stabilizing transthyretin and for treating, preventing, or ameliorating one or more symptoms of transthyretin mediated diseases. In one embodiment, the compounds are benzoxazoles and related compounds.

  提供了稳定甲状腺素转运蛋白和治疗、预防或改善甲状腺素转运蛋白介导疾病的复合物、组合物和方法。在一种实施例中，化合物是苯并噁唑和相关化合物。
• Direct C–H Bond Arylation of (Benzo)oxazoles with Aryl Chlorides Catalyzed by <i>N</i>-Heterocyclic Carbene–Palladium(II)–1-Methylimidazole Complex
  作者：Xiao-Bao Shen、Yun Zhang、Wen-Xin Chen、Zheng-Kang Xiao、Ting-Ting Hu、Li-Xiong Shao

  DOI：10.1021/ol500531m

  日期：2014.4.4

  The direct C-H bond arylation of (benzo)oxazoles with aryl chlorides was achieved catalyzed by a well-defined NHC-Pd(II)-Im complex. Under the optimal conditions, various aryl chlorides were successfully applied as the arylating reagents to achieve the 2-aryl (benzo)oxazoles in acceptable to high yields, providing a convenient and alternative method for the direct C-H bond arylation of (benzo)oxazoles and enriching the chemistry of the NHC-Pd(II) complex in organic synthesis.