(S)-2-((S)-2-acryloyloxy-4-methylpent-4-enyl)-piperidine-1-carboxylic acid tert-butyl ester | 1150660-05-1

• 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-((S)-2-acryloyloxy-4-methylpent-4-enyl)-piperidine-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (2S)-2-[(2S)-4-methyl-2-prop-2-enoyloxypent-4-enyl]piperidine-1-carboxylate
• CAS: 1150660-05-1
• 化学式: C₁₉H₃₁NO₄
• 分子量: 337.459
• InChiKey: KPEVBQRFLDNLHA-HOTGVXAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 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-((S)-2-acryloyloxy-4-methylpent-4-enyl)-piperidine-1-carboxylic acid tert-butyl ester 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以60%的产率得到(S)-2-((S)-4-methyl-6-oxo-3,6-dihydro-2H-pyran-2-ylmethyl)piperidine-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：

  (S)-2-((S)-2-hydroxy-4-methylpent-4-enyl)-piperidine-1-carboxylic acid tert-butyl ester 、 丙烯酰氯 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以83%的产率得到(S)-2-((S)-2-acryloyloxy-4-methylpent-4-enyl)-piperidine-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