(E)-6-(2-benzyloxycarbonylaminophenyl)-3-hexen-2-one | 1361525-08-7

• 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: (E)-6-(2-benzyloxycarbonylaminophenyl)-3-hexen-2-one
• CAS: 1361525-08-7
• 化学式: C₂₀H₂₁NO₃
• 分子量: 323.392
• InChiKey: ROPUHKJGQGJGDI-WEVVVXLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.51
• 重原子数：
  24.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (E)-6-(2-benzyloxycarbonylaminophenyl)-3-hexen-2-one 在 (6-甲氧基-4-喹啉基)-(5-乙烯基奎宁环-2-基)甲胺 、 五氟丙酸 作用下， 以 氯仿 为溶剂， 反应 1.0h， 生成 (2S)-N-benzyloxycarbonyl-2-(2-oxopropyl)-1,2,3,4-tetrahydroquinoline 、 (2R)-N-benzyloxycarbonyl-2-(2-oxopropyl)-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  Microwave-Assisted Organocatalytic Enantioselective Intramolecular aza-Michael Reaction with α,β-Unsaturated Ketones

  摘要：

  AbstractAn organocatalytic enantioselective intramolecular aza‐Michael reaction of carbamates bearing conjugated ketones as Michael acceptors is described. By using 9‐amino‐9‐deoxy‐epi‐hydroquinine as the catalyst and pentafluoropropionic acid as a co‐catalyst, a series of piperidines, pyrrolidines, and the corresponding benzo‐fused derivatives (indolines, isoindolines, tetrahydroquinolines, and tetrahydroisoquinolines) can be obtained in excellent yields and enantioselectivities. In addition, the use of microwave irradiation at 60 °C improves the efficiency of the process giving rise to the final products with comparable yields and enantiomeric excesses. Some mechanistic insights are also considered.

  DOI：

  10.1002/chem.201101292
• 作为产物：
  描述：

  N-benzyloxycarbonyl-2-homoallylaniline 、 丁烯酮 在 Hoveyda-Grubbs catalyst second generation 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以89%的产率得到(E)-6-(2-benzyloxycarbonylaminophenyl)-3-hexen-2-one
  参考文献：
  名称：

  Microwave-Assisted Organocatalytic Enantioselective Intramolecular aza-Michael Reaction with α,β-Unsaturated Ketones

  摘要：

  AbstractAn organocatalytic enantioselective intramolecular aza‐Michael reaction of carbamates bearing conjugated ketones as Michael acceptors is described. By using 9‐amino‐9‐deoxy‐epi‐hydroquinine as the catalyst and pentafluoropropionic acid as a co‐catalyst, a series of piperidines, pyrrolidines, and the corresponding benzo‐fused derivatives (indolines, isoindolines, tetrahydroquinolines, and tetrahydroisoquinolines) can be obtained in excellent yields and enantioselectivities. In addition, the use of microwave irradiation at 60 °C improves the efficiency of the process giving rise to the final products with comparable yields and enantiomeric excesses. Some mechanistic insights are also considered.

  DOI：

  10.1002/chem.201101292