N-(3-(2-oxopyrrolidin-1-yl)phenyl)cyclohexanecarboxamide | 922926-09-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: N-(3-(2-oxopyrrolidin-1-yl)phenyl)cyclohexanecarboxamide
• 英文别名: N-[3-(2-oxopyrrolidin-1-yl)phenyl]cyclohexanecarboxamide
• CAS: 922926-09-8
• 化学式: C₁₇H₂₂N₂O₂
• 分子量: 286.374
• InChiKey: KEHDFDMCFCBEJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(3-(2-oxopyrrolidin-1-yl)phenyl)cyclohexanecarboxamide 在 air 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 邻二氯苯 为溶剂， 120.0 ℃ 、101.33 kPa 条件下， 反应 12.0h， 以76%的产率得到1-(2-cyclohexylbenzoxazol-7-yl)pyrrolidin-2-one
  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
• 作为产物：
  描述：

  1-(3-氨基苯)吡咯烷-2-酮 、 环己甲酰氯 在 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 反应 4.0h， 以91%的产率得到N-(3-(2-oxopyrrolidin-1-yl)phenyl)cyclohexanecarboxamide
  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