(2R,6S)-2-(2-oxoethyl)-6-methylpiperidine-1-carboxylic acid tert-butyl ester | 1150660-12-0

• 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: (2R,6S)-2-(2-oxoethyl)-6-methylpiperidine-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (2S,6R)-2-methyl-6-(2-oxoethyl)piperidine-1-carboxylate
• CAS: 1150660-12-0
• 化学式: C₁₃H₂₃NO₃
• 分子量: 241.331
• InChiKey: LEOSDSPYIPKYKP-WDEREUQCSA-N

物化性质

• 沸点：
  327.4±15.0 °C(predicted)
• 密度：
  1.007±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,6S)-2-(2-oxoethyl)-6-methylpiperidine-1-carboxylic acid tert-butyl ester 、 甲基三苯基碘化膦 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 以53%的产率得到(2R,6S)-2-allyl-6-methylpiperidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Enantiopure N-Boc piperidine-2-ethanol for the synthesis of (+)- and (−)-dumetorine, and (+)- and (−)-epidihydropinidine

  摘要：

  The convenient synthesis of both enantiomers of the piperidine alkaloids such as dumetorine and epidihydropinidine is described. Pure enantiomers of 2-(2-hydroxy-ethyl)-piperidine-1-carboxylic acid tert-butyl ester are used as a common starting material. The syntheses are based on a RCM reaction and on methylation of the piperidine ring according to Beak-Lee methodology, respectively. (C) 2008 Elsevier Ltd. All rights reserved

  DOI：

  10.1016/j.tetasy.2008.12.008
• 作为产物：
  描述：

  (2R,6S)-2-(2-hydroxyethyl)-6-methylpiperidine-1-carboxylic acid tert-butyl ester 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以99%的产率得到(2R,6S)-2-(2-oxoethyl)-6-methylpiperidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Enantiopure N-Boc piperidine-2-ethanol for the synthesis of (+)- and (−)-dumetorine, and (+)- and (−)-epidihydropinidine

  摘要：

  The convenient synthesis of both enantiomers of the piperidine alkaloids such as dumetorine and epidihydropinidine is described. Pure enantiomers of 2-(2-hydroxy-ethyl)-piperidine-1-carboxylic acid tert-butyl ester are used as a common starting material. The syntheses are based on a RCM reaction and on methylation of the piperidine ring according to Beak-Lee methodology, respectively. (C) 2008 Elsevier Ltd. All rights reserved

  DOI：

  10.1016/j.tetasy.2008.12.008

文献信息

• Enantiopure N-Boc piperidine-2-ethanol for the synthesis of (+)- and (−)-dumetorine, and (+)- and (−)-epidihydropinidine
  作者：Daniele Passarella、Sergio Riva、Gabriele Grieco、Francesco Cavallo、Begoña Checa、Federica Arioli、Elena Riva、Daniela Comi、Bruno Danieli

  DOI：10.1016/j.tetasy.2008.12.008

  日期：2009.2

  The convenient synthesis of both enantiomers of the piperidine alkaloids such as dumetorine and epidihydropinidine is described. Pure enantiomers of 2-(2-hydroxy-ethyl)-piperidine-1-carboxylic acid tert-butyl ester are used as a common starting material. The syntheses are based on a RCM reaction and on methylation of the piperidine ring according to Beak-Lee methodology, respectively. (C) 2008 Elsevier Ltd. All rights reserved