ethyl (3S,4R,6R)-1-benzyl-6-hydroxy-4-naphthalen-2-yl-2-oxopiperidine-3-carboxylate | 1345157-55-2

• 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: ethyl (3S,4R,6R)-1-benzyl-6-hydroxy-4-naphthalen-2-yl-2-oxopiperidine-3-carboxylate
• CAS: 1345157-55-2
• 化学式: C₂₅H₂₅NO₄
• 分子量: 403.478
• InChiKey: BCIVYEAEYHMOGO-ZRBLBEILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (2E)-3-(2-萘基)丙烯醛 、 乙基(N-苄基氨基甲酰基)乙酸酯 在 (2S)-2-[二苯基[(三甲基硅酯)氧基]甲基]-吡咯烷 、 potassium acetate 作用下， 以 2,2,2-三氟乙醇 为溶剂， 生成 、 ethyl (3S,4R,6R)-1-benzyl-6-hydroxy-4-naphthalen-2-yl-2-oxopiperidine-3-carboxylate
  参考文献：
  名称：

  Highly enantioselective organocatalytic synthesis of piperidines. Formal synthesis of (−)-Paroxetine

  摘要：

  A highly enantioselective organocatalytic synthesis of piperidines is reported. The reaction is catalyzed by simple and commercially available secondary amines, affording the corresponding adducts with high yields and enantioselectivities. Moreover, this reaction is used for the formal synthesis of (-)-Paroxetine, a blockbuster drug, in only three steps. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.02.049

文献信息

• Highly enantioselective organocatalytic synthesis of piperidines. Formal synthesis of (−)-Paroxetine
  作者：Guillem Valero、Jiri Schimer、Ivana Cisarova、Jan Vesely、Albert Moyano、Ramon Rios

  DOI：10.1016/j.tetlet.2009.02.049

  日期：2009.4

  A highly enantioselective organocatalytic synthesis of piperidines is reported. The reaction is catalyzed by simple and commercially available secondary amines, affording the corresponding adducts with high yields and enantioselectivities. Moreover, this reaction is used for the formal synthesis of (-)-Paroxetine, a blockbuster drug, in only three steps. (C) 2009 Elsevier Ltd. All rights reserved.