(S)-2-(2-acetoxy-ethyl)-piperidine-1-carboxylic acid tert-butyl ester | 639458-49-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (S)-2-(2-acetoxy-ethyl)-piperidine-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (2S)-2-(2-acetyloxyethyl)piperidine-1-carboxylate
• CAS: 639458-49-4
• 化学式: C₁₄H₂₅NO₄
• 分子量: 271.357
• InChiKey: WHHORRRNBFCREF-LBPRGKRZSA-N

物化性质

• 沸点：
  339.2±15.0 °C(Predicted)
• 密度：
  1.048±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-(2-acetoxy-ethyl)-piperidine-1-carboxylic acid tert-butyl ester 在 lithium aluminium tetrahydride 、 草酰氯 、 sodium carbonate 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 sedamine
  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
• 作为产物：
  描述：

  乙酸乙烯酯 、 N-叔丁氧羰基-2-哌啶-2-基乙醇 生成 (S)-2-(2-acetoxy-ethyl)-piperidine-1-carboxylic acid tert-butyl 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

• Enzyme assisted enantioselective synthesis of the alkaloid (+)-aloperine
  作者：Alessio Barilli、Francesca Belinghieri、Daniele Passarella、Giordano Lesma、Sergio Riva、Alessandra Silvani、Bruno Danieli

  DOI：10.1016/j.tetasy.2004.06.056

  日期：2004.9

  The enantioselective synthesis of the lupinine alkaloid (+)-aloperine is described. The synthetic scheme presents three steps that are mediated by enzymes: kinetic resolution, oxidation of a primary alcohol to an aldehyde and oxidation of a secondary alcohol to a ketone. (C) 2004 Elsevier Ltd. All rights reserved.