2-(3-phenoxyphenyl)benzoxazole | 1152493-76-9

• 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-(3-phenoxyphenyl)benzoxazole
• 英文别名: 2-(3-phenoxyphenyl)-1,3-benzoxazole
• CAS: 1152493-76-9
• 化学式: C₁₉H₁₃NO₂
• 分子量: 287.318
• InChiKey: KTNCDXQIGSZHBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  22
• 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：
  35.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-phenoxy-N-phenylbenzamide 在 air 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 邻二氯苯 为溶剂， 160.0 ℃ 、101.33 kPa 条件下， 反应 28.0h， 以79%的产率得到2-(3-phenoxyphenyl)benzoxazole
  参考文献：
  名称：

  Copper-Catalyzed Synthesis of Benzoxazoles via a Regioselective C−H Functionalization/C−O Bond Formation under an Air Atmosphere

  摘要：

  An efficient method for the synthesis of functionalized benzoxazoles is described that involves a copper(II)-catalyzed regioselective C-H functionalization/C-O bond formation protocol. The use of dichlorobenzene as a solvent at 160 degrees C allows the use of air as the tern-final oxidant in the catalytic synthesis of benzoxazoles in a process that has high functional group tolerance. The presence of a directing group at the meta position markedly improves the reaction efficacy and a variety of 7-substituted benzoxazoles are selectively produced under mild reaction conditions. The mechanism of the reaction is also discussed in this report.

  DOI：

  10.1021/jo900513z

文献信息

• Dess-Martin Periodinane Mediated Intramolecular Cyclization of Phenolic Azomethines: A Solution-Phase Strategy toward Benzoxazoles and Benzothiazoles
  作者：D. Bose、Mohd. Idrees

  DOI：10.1055/s-0029-1217136

  日期：2010.2

  Dess-Martin periodinane (DMP), a highly versatile hypervalent iodine(V) reagent, was found to efficiently mediate the intramolecular cyclization of phenolic azomethines/Schiff bases at ambient temperature leading to the rapid and expeditious synthesis of substituted benzoxazoles and benzothiazoles. Furthermore, a solution-phase strategy has been developed by treating the reaction mixtures sequentially with Amberlyst A-26 thiosulfate resin and diisopropylaminomethyl resin (PS-DIEA), which remove excess reagent and byproducts, to give pure products.

  研究发现，Dess-Martin periodinane（DMP）是一种用途广泛的高价碘（V）试剂，可在常温下有效地介导酚偶氮甲烷/席夫碱的分子内环化反应，从而快速合成取代的苯并恶唑和苯并噻唑。此外，还开发了一种溶液相策略，即用 Amberlyst A-26 硫代硫酸盐树脂和二异丙基氨基甲基树脂（PS-DIEA）依次处理反应混合物，从而去除多余的试剂和副产品，得到纯净的产品。
• Synthesis of 2-(3-phenoxyphenyl)-substituted benzoxazoles, based on nitriles containing the diphenyl oxide fragment
  作者：Yu. V. Popov、T. K. Korchagina、V. S. Lobasenko

  DOI：10.1007/s10593-011-0822-0

  日期：2011.9
• Copper-Catalyzed Synthesis of Benzoxazoles via a Regioselective C−H Functionalization/C−O Bond Formation under an Air Atmosphere
  作者：Satoshi Ueda、Hideko Nagasawa

  DOI：10.1021/jo900513z

  日期：2009.6.5

  An efficient method for the synthesis of functionalized benzoxazoles is described that involves a copper(II)-catalyzed regioselective C-H functionalization/C-O bond formation protocol. The use of dichlorobenzene as a solvent at 160 degrees C allows the use of air as the tern-final oxidant in the catalytic synthesis of benzoxazoles in a process that has high functional group tolerance. The presence of a directing group at the meta position markedly improves the reaction efficacy and a variety of 7-substituted benzoxazoles are selectively produced under mild reaction conditions. The mechanism of the reaction is also discussed in this report.