(6R,1R,2S)-(+)-6-(1-hydroxypropyl)-1-(2-methoxymethylpyrrolidin-1-yl)piperidin-2-one | 1043481-64-6

• 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: (6R,1R,2S)-(+)-6-(1-hydroxypropyl)-1-(2-methoxymethylpyrrolidin-1-yl)piperidin-2-one
• 英文别名: (6R)-6-[(1R)-1-hydroxypropyl]-1-[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]piperidin-2-one
• CAS: 1043481-64-6
• 化学式: C₁₄H₂₆N₂O₃
• 分子量: 270.372
• InChiKey: VKUHGXSONHSVNZ-YNEHKIRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  53
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (6R,1R,2S)-(+)-6-(1-hydroxypropyl)-1-(2-methoxymethylpyrrolidin-1-yl)piperidin-2-one 在 硼烷 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以68%的产率得到(+)-β-conhydrine
  参考文献：
  名称：

  Asymmetric synthesis of the optically active piperidine alkaloid (+)-β-conhydrine

  摘要：

  A new approach for the stereoselective synthesis of the piperidine alkaloid (+)-beta-conhydrine based upon a highly diastereoselective 1,2-nucleophilic addition reaction onto a diastereopure hydrazone and ring-closing metathesis as the key steps has been developed. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.04.021
• 作为产物：
  描述：

  (6R,1R,2S)-(+)-6-(1-benzyloxypropyl)-1-(2-methoxymethylpyrrolidin-1-yl)-5,6-dihydro-1H-pyridin-2-one 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 12.0h， 以95%的产率得到(6R,1R,2S)-(+)-6-(1-hydroxypropyl)-1-(2-methoxymethylpyrrolidin-1-yl)piperidin-2-one
  参考文献：
  名称：

  Asymmetric synthesis of the optically active piperidine alkaloid (+)-β-conhydrine

  摘要：

  A new approach for the stereoselective synthesis of the piperidine alkaloid (+)-beta-conhydrine based upon a highly diastereoselective 1,2-nucleophilic addition reaction onto a diastereopure hydrazone and ring-closing metathesis as the key steps has been developed. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.04.021

文献信息

• Asymmetric synthesis of the optically active piperidine alkaloid (+)-β-conhydrine
  作者：Stéphane Lebrun、Axel Couture、Eric Deniau、Pierre Grandclaudon

  DOI：10.1016/j.tetasy.2008.04.021

  日期：2008.5

  A new approach for the stereoselective synthesis of the piperidine alkaloid (+)-beta-conhydrine based upon a highly diastereoselective 1,2-nucleophilic addition reaction onto a diastereopure hydrazone and ring-closing metathesis as the key steps has been developed. (C) 2008 Elsevier Ltd. All rights reserved.