N,5-diphenyl-1,3-oxazole-4-carboxamide

• 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: N,5-diphenyl-1,3-oxazole-4-carboxamide
• 化学式: C₁₆H₁₂N₂O₂
• 分子量: 264.283
• InChiKey: QZHYXBRLJHISAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  55.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯基三甲氧基硅烷 、 5-phenyloxazole-4-carboxamide 在 四丁基氟化铵 、 copper diacetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以27%的产率得到N,5-diphenyl-1,3-oxazole-4-carboxamide
  参考文献：
  名称：

  α-Nitrogen activating effect in the room temperature copper-promoted N-arylation of heteroarylcarboxamides with phenyl siloxane or p-toluylboronic acid

  摘要：

  Heteroarylcarboxamides containing a-nitrogens undergo copper-promoted N-phenylation with hypervalent phenyl trimethylsiloxane at room temperature, in the absence of base and in air. Arylboronic acid can substitute for phenyl trimethylsiloxane as the organometalloid. The ol-heteroatom chelating effect is in the decreasing order of N>O, S. This discovery opens up the possibility of using other alpha -nitrogen functional groups to direct the N-arylation of peptides and simple amides under conditions as mild as that of amide bond formation. (C) 2001 Dupont Pharmaceutical Company. Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00203-9

文献信息

• α-Nitrogen activating effect in the room temperature copper-promoted N-arylation of heteroarylcarboxamides with phenyl siloxane or p-toluylboronic acid
  作者：Patrick Y.S Lam、Sophie Deudon、Elisabeth Hauptman、Charles G Clark

  DOI：10.1016/s0040-4039(01)00203-9

  日期：2001.3

  Heteroarylcarboxamides containing a-nitrogens undergo copper-promoted N-phenylation with hypervalent phenyl trimethylsiloxane at room temperature, in the absence of base and in air. Arylboronic acid can substitute for phenyl trimethylsiloxane as the organometalloid. The ol-heteroatom chelating effect is in the decreasing order of N>O, S. This discovery opens up the possibility of using other alpha -nitrogen functional groups to direct the N-arylation of peptides and simple amides under conditions as mild as that of amide bond formation. (C) 2001 Dupont Pharmaceutical Company. Published by Elsevier Science Ltd. All rights reserved.