2-(2-hydroxy-ethyl)-piperidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester | 155229-77-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 2-(2-hydroxy-ethyl)-piperidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester
• 英文别名: (9H-fluoren-9-yl)methyl 2-(2-hydroxyethyl)piperidine-1-carboxylate；9H-fluoren-9-ylmethyl 2-(2-hydroxyethyl)piperidine-1-carboxylate
• CAS: 155229-77-9
• 化学式: C₂₂H₂₅NO₃
• 分子量: 351.445
• InChiKey: QLJZHVTVXRVZGI-UHFFFAOYSA-N

物化性质

• 沸点：
  528.9±23.0 °C(Predicted)
• 密度：
  1.193±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-哌啶乙醇 、 (9H-芴-9-基)甲基 2,5-二氧代吡咯烷-1-羧酸 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以85%的产率得到2-(2-hydroxy-ethyl)-piperidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester
  参考文献：
  名称：

  Remote Stereocenter Discrimination in the Enzymatic Resolution of Piperidine-2-ethanol. Short Enantioselective Synthesis of Sedamine and Allosedamine

  摘要：

  Kinetic resolution of N-Boc-piperidine-2-ethanol (2), a case of remote stereocenter discrimination, was accomplished by sequential transesterification mediated by two enzymes, Lipase PS and porcine pancreatic lipase, showing opposite enantioselectivity. The gram-scale availability of the two enantiomeric N-Boc alcohols 2a (R) and 2c (S) enlarges their synthetic exploitation for the enantioselective preparation of piperidine alkaloids. As an example, the convenient three-step synthesis of both the enantiomers of sedamine and allosedamine is described.

  DOI：

  10.1021/jo035215g

文献信息

• JPH0614798A
  申请人：——

  公开号：JPH0614798A

  公开（公告）日：1994-01-25
• Remote Stereocenter Discrimination in the Enzymatic Resolution of Piperidine-2-ethanol. Short Enantioselective Synthesis of Sedamine and Allosedamine
  作者：Marco Angoli、Alessio Barilli、Giordano Lesma、Daniele Passarella、Sergio Riva、Alessandra Silvani、Bruno Danieli

  DOI：10.1021/jo035215g

  日期：2003.11.1

  Kinetic resolution of N-Boc-piperidine-2-ethanol (2), a case of remote stereocenter discrimination, was accomplished by sequential transesterification mediated by two enzymes, Lipase PS and porcine pancreatic lipase, showing opposite enantioselectivity. The gram-scale availability of the two enantiomeric N-Boc alcohols 2a (R) and 2c (S) enlarges their synthetic exploitation for the enantioselective preparation of piperidine alkaloids. As an example, the convenient three-step synthesis of both the enantiomers of sedamine and allosedamine is described.