(8R)-2-phenyl-8-benzoyloxy-5,6,7,8-tetrahydroquinoline | 887922-04-5

• 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: (8R)-2-phenyl-8-benzoyloxy-5,6,7,8-tetrahydroquinoline
• 英文别名: [(8R)-2-phenyl-5,6,7,8-tetrahydroquinolin-8-yl] benzoate
• CAS: 887922-04-5
• 化学式: C₂₂H₁₉NO₂
• 分子量: 329.398
• InChiKey: SWNBNWGFQWSFKI-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (8R)-2-phenyl-8-benzoyloxy-5,6,7,8-tetrahydroquinoline 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以89%的产率得到(R)-8-hydroxy-2-phenyl-5,6,7,8-tetrahydroquinoline
  参考文献：
  名称：

  Kinetic Resolution of Pyridyl Alcohols by Cu(II)(Borabox)-Catalyzed Acylation

  摘要：

  利用铜(II)(硼硼氧烷)催化的苯甲酰化作用实现了吡啶醇的动力学解析。观察到的选择性因子（krel）高达 125，并介绍了其在手性吡啶膦配体合成中的应用。

  DOI：

  10.1055/s-2007-983850
• 作为产物：
  描述：

  2-苯基-5,6,7,8-四氢喹啉 在 chiral boron-bridged bisoxazoline-based ligand 、 N,N-二异丙基乙胺 、 间氯过氧苯甲酸 、 三氟乙酸酐 、 copper dichloride 作用下， 以 二氯甲烷 为溶剂， 反应 50.0h， 生成 (8R)-2-phenyl-8-benzoyloxy-5,6,7,8-tetrahydroquinoline
  参考文献：
  名称：

  Kinetic Resolution of Diols and Pyridyl Alcohols by Cu(II)(borabox)-Catalyzed Acylation

  摘要：

  Boron-bridged bisoxazoline (borabox) ligands have been used in the copper(II)-catalyzed benzoylation of pyridyl alcohols and 1,2-diols. Efficient kinetic resolution of 1,2-diols was achieved using both borabox and bisoxazoline (box) ligands. Borabox ligands induced high selectivities in the benzoylation of suitable pyridyl alcohols, where they outperformed bisoxazolines. In addition, highly enantioselective Cu(II)(borabox)catalyzed benzoylation has been used for the synthesis of both enantiomers of a pyridyl alcohol.

  DOI：

  10.1021/ol060443t

文献信息

• Kinetic Resolution of Diols and Pyridyl Alcohols by Cu(II)(borabox)-Catalyzed Acylation
  作者：Clément Mazet、Stephen Roseblade、Valentin Köhler、Andreas Pfaltz

  DOI：10.1021/ol060443t

  日期：2006.4.1

  Boron-bridged bisoxazoline (borabox) ligands have been used in the copper(II)-catalyzed benzoylation of pyridyl alcohols and 1,2-diols. Efficient kinetic resolution of 1,2-diols was achieved using both borabox and bisoxazoline (box) ligands. Borabox ligands induced high selectivities in the benzoylation of suitable pyridyl alcohols, where they outperformed bisoxazolines. In addition, highly enantioselective Cu(II)(borabox)catalyzed benzoylation has been used for the synthesis of both enantiomers of a pyridyl alcohol.
• Kinetic Resolution of Pyridyl Alcohols by Cu(II)(Borabox)-Catalyzed Acylation
  作者：Andreas Pfaltz、Stephen Roseblade

  DOI：10.1055/s-2007-983850

  日期：2007.12

  Kinetic resolution of pyridyl alcohols has been achieved using copper(II)(borabox)-catalyzed benzoylation. Selectivity factors (krel) of up to 125 have been observed and application to the synthesis of chiral pyridyl phosphine ligands is described.

  利用铜(II)(硼硼氧烷)催化的苯甲酰化作用实现了吡啶醇的动力学解析。观察到的选择性因子（krel）高达 125，并介绍了其在手性吡啶膦配体合成中的应用。