2-(4-chlorophenylethynyl)-5-methylbenzoxazole | 1221576-86-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: 2-(4-chlorophenylethynyl)-5-methylbenzoxazole
• 英文别名: 2-[2-(4-Chlorophenyl)ethynyl]-5-methyl-1,3-benzoxazole；2-[2-(4-chlorophenyl)ethynyl]-5-methyl-1,3-benzoxazole
• CAS: 1221576-86-8
• 化学式: C₁₆H₁₀ClNO
• 分子量: 267.714
• InChiKey: WICNJLZVHYKVEG-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：
  0.06
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-氯苯乙炔 、 5-甲基苯并唑 在 四(三苯基膦)钯 、 lithium tert-butoxide 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以64%的产率得到2-(4-chlorophenylethynyl)-5-methylbenzoxazole
  参考文献：
  名称：

  Palladium-Catalyzed Oxidative Alkynylation of Heterocycles with Terminal Alkynes under Air Conditions

  摘要：

  Pd-Catalyzed oxidative alkynylation of azoles with terminal alkynes was developed via simultaneous activation of both heterocyclic sp(2) C-H and alkynyl sp C-H bonds. The choice of palladium catalyst source and external base resulted in being important factors for performing the reaction with high efficiency and selectivity, and air was successfully utilized as an environmental oxidant in the present alkynylation procedure.

  DOI：

  10.1021/ol200154s

文献信息

• Highly Efficient and Versatile Pd-Catalyzed Direct Alkynylation of Both Azoles and Azolines
  作者：Seok Hwan Kim、Sukbok Chang

  DOI：10.1021/ol100488v

  日期：2010.4.16

  A highly efficient and versatile Pd-catalyzed direct alkynylation reaction of heterocycles with 1-bromoalkynes was developed. The substrate scope of the reaction was very broad to include not only azoles but also azolines for the first time, thus offering an important advance in the direct functionalization of heterocycles.

  开发了一种高效且通用的Pd催化杂环与1-溴代炔烃的直接炔基化反应。反应的底物范围非常广泛，首次不仅包括唑类，而且还包括偶氮类，因此在杂环的直接官能化方面提供了重要的进展。
• Ligand and solvent-free iron catalyzed oxidative alkynylation of azoles with terminal alkynes
  作者：Sachin S. Patil、Rahul P. Jadhav、Sachin V. Patil、Vivek D. Bobade

  DOI：10.1016/j.tetlet.2011.08.083

  日期：2011.10

  A highly efficient and versatile iron catalyzed oxidative alkynylation of azoles with terminal alkynes under ligand and solvent-free conditions is described. (C) 2011 Elsevier Ltd. All rights reserved.
• Palladium-Catalyzed Oxidative Alkynylation of Heterocycles with Terminal Alkynes under Air Conditions
  作者：Seok Hwan Kim、Jungho Yoon、Sukbok Chang

  DOI：10.1021/ol200154s

  日期：2011.3.18

  Pd-Catalyzed oxidative alkynylation of azoles with terminal alkynes was developed via simultaneous activation of both heterocyclic sp(2) C-H and alkynyl sp C-H bonds. The choice of palladium catalyst source and external base resulted in being important factors for performing the reaction with high efficiency and selectivity, and air was successfully utilized as an environmental oxidant in the present alkynylation procedure.