(R)-phenoperidine

• 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: (R)-phenoperidine
• 英文别名: ethyl 1-[(3R)-3-hydroxy-3-phenylpropyl]-4-phenylpiperidine-4-carboxylate
• 化学式: C₂₃H₂₉NO₃
• 分子量: 367.488
• InChiKey: IPOPQVVNCFQFRK-OAQYLSRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  去甲哌替啶 、 (R)-3-phenyl-3-hydroxypropanal 在 sodium sulfate 、 三乙酰氧基硼氢化钠 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以40 mg的产率得到(R)-phenoperidine
  参考文献：
  名称：

  A site isolation-enabled organocatalytic approach to enantiopure γ-amino alcohol drugs

  摘要：

  Solid support-enabled site isolation has previously allowed to use paraldehyde as an acetaldehyde surrogate in aldol reactions. However, only electron-poor aldehydes were tolerated by the system. Herein, we show that the temporary conversion of benzaldehyde into eta(6)-benzaldehyde Cr(CO)(3) circumvents this limitation. Asymmetric synthesis of (R)-Phenoperidine, as well as formal syntheses of (R)Fluoxetine and (R)-Atomoxetine, illustrate the benefits of this strategy. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2018.04.022

文献信息

• A site isolation-enabled organocatalytic approach to enantiopure γ-amino alcohol drugs
  作者：Shoulei Wang、Carles Rodríguez-Escrich、Xinyuan Fan、Miquel A. Pericàs

  DOI：10.1016/j.tet.2018.04.022

  日期：2018.7

  Solid support-enabled site isolation has previously allowed to use paraldehyde as an acetaldehyde surrogate in aldol reactions. However, only electron-poor aldehydes were tolerated by the system. Herein, we show that the temporary conversion of benzaldehyde into eta(6)-benzaldehyde Cr(CO)(3) circumvents this limitation. Asymmetric synthesis of (R)-Phenoperidine, as well as formal syntheses of (R)Fluoxetine and (R)-Atomoxetine, illustrate the benefits of this strategy. (C) 2018 Elsevier Ltd. All rights reserved.