(2R)-N-benzyloxycarbonyl-2-(2-oxopropyl)-1,2,3,4-tetrahydroquinoline | 1361525-16-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (2R)-N-benzyloxycarbonyl-2-(2-oxopropyl)-1,2,3,4-tetrahydroquinoline
• 英文别名: benzyl (2R)-2-(2-oxopropyl)-3,4-dihydro-2H-quinoline-1-carboxylate
• CAS: 1361525-16-7
• 化学式: C₂₀H₂₁NO₃
• 分子量: 323.392
• InChiKey: OKPCQCDYYSCPBB-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-benzyloxycarbonyl-2-homoallylaniline 在 (6-甲氧基-4-喹啉基)-(5-乙烯基奎宁环-2-基)甲胺 、 Hoveyda-Grubbs catalyst second generation 、 五氟丙酸 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 13.0h， 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

文献信息

• Microwave-Assisted Organocatalytic Enantioselective Intramolecular aza-Michael Reaction with α,β-Unsaturated Ketones
  作者：Santos Fustero、Carlos del Pozo、Cristina Mulet、Rubén Lazaro、María Sánchez-Roselló

  DOI：10.1002/chem.201101292

  日期：2011.12.9

  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.