5-phenyl-2-(phenylethynyl)benzoxazole | 1226889-95-7

• 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: 5-phenyl-2-(phenylethynyl)benzoxazole
• 英文别名: 5-phenyl-2-(phenylethynyl)benzo[d]oxazole；5-Phenyl-2-(2-phenylethynyl)-1,3-benzoxazole
• CAS: 1226889-95-7
• 化学式: C₂₁H₁₃NO
• 分子量: 295.34
• InChiKey: DVGWFOXUHFPFIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  5-phenylbenzoxazole 、 苯乙炔 在 NiBr2*diglyme 、 氧气 、 4,4'-二叔丁基-2,2'-二吡啶 、 lithium tert-butoxide 作用下， 以 甲苯 为溶剂， 50.0 ℃ 、101.33 kPa 条件下， 以55%的产率得到5-phenyl-2-(phenylethynyl)benzoxazole
  参考文献：
  名称：

  在O 2或大气条件下，镍和铜催化的氮杂腈和多氟芳烃与末端炔烃的直接炔基化

  摘要：

  在镍/ O 2催化体系下，唑类与末端炔烃的直接CH炔基化反应有效进行。另一方面，铜/空气催化剂能够使多氟芳烃与末端炔烃偶联。这些催化剂通过正式的直接Sonogashira偶联为芳基乙炔提供了新的途径。

  DOI：

  10.1021/ol100699g

文献信息

• 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.
• Dehydrogenative and decarboxylative C–H alkynylation of heteroarenes catalyzed by Pd(II)–carbene complex
  作者：Thupakula Parsharamulu、Police Vishnuvardhan Reddy、Pravin R. Likhar、Mannepalli Lakshmi Kantam

  DOI：10.1016/j.tet.2015.02.020

  日期：2015.4

  The direct alkynylation of heteroarenes was accomplished with easily prepared Pd(II) carbene complex (Pd Cat.) by two complementary strategies. Pd Cat. catalysed cross-dehydrogenative coupling of terminal alkynes with heteroarenes was achieved in the first method and decarboxylative coupling of aryl propiolic acids with heteroarenes was investigated in the second method. Both the methodologies tolerate a broad variety of heteroarenes that include benzoxazoles, benzothiazoles, imidazole and benzimidazoles. (C) 2015 Elsevier Ltd. All rights reserved.