methyl (E)-3-[(2R,3S)-1-acetyl-3-[acetyl(benzyl)amino]pyrrolidin-2-yl]prop-2-enoate | 203982-62-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: methyl (E)-3-[(2R,3S)-1-acetyl-3-[acetyl(benzyl)amino]pyrrolidin-2-yl]prop-2-enoate
• CAS: 203982-62-1
• 化学式: C₁₉H₂₄N₂O₄
• 分子量: 344.411
• InChiKey: SVRDMDUVYVOXKG-UIVAWZFMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  66.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (E)-3-[(2R,3S)-1-acetyl-3-[acetyl(benzyl)amino]pyrrolidin-2-yl]prop-2-enoate 在 palladium on activated charcoal 氢气 作用下， 以97%的产率得到methyl 3-[(2R,3S)-1-acetyl-3-[acetyl(benzyl)amino]pyrrolidin-2-yl]propanoate
  参考文献：
  名称：

  Stereoselective synthesis of (2S,3S)-3-N-benzylaminoprolinol and (7S,8R)-7-N-benzylaminopyrrolizidin-3-one

  摘要：

  The highly stereoselective synthesis of of (2S,3S)-3N-benzylaminoprolinol and derivatives involved the conjugate addition of N-benzylamine to alpha,beta-unsaturated lactam 2. Wittig-Horner reactions with 1-acetyl-3-N-acetyl-N-benzylaminoprolinal provided a simple access to (7S,8R)-7-N-benzylaminopyrrolizidin-3-one. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10749-3
• 作为产物：
  描述：

  (4S,5S)-4-N-benzylamino-5-hydroxymethylpyrrolidin-2-one 在 吡啶 、 lithium aluminium tetrahydride 、 三氧化硫 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 生成 methyl (E)-3-[(2R,3S)-1-acetyl-3-[acetyl(benzyl)amino]pyrrolidin-2-yl]prop-2-enoate
  参考文献：
  名称：

  Stereoselective synthesis of (2S,3S)-3-N-benzylaminoprolinol and (7S,8R)-7-N-benzylaminopyrrolizidin-3-one

  摘要：

  The highly stereoselective synthesis of of (2S,3S)-3N-benzylaminoprolinol and derivatives involved the conjugate addition of N-benzylamine to alpha,beta-unsaturated lactam 2. Wittig-Horner reactions with 1-acetyl-3-N-acetyl-N-benzylaminoprolinal provided a simple access to (7S,8R)-7-N-benzylaminopyrrolizidin-3-one. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10749-3

文献信息

• Stereoselective synthesis of (2S,3S)-3-N-benzylaminoprolinol and (7S,8R)-7-N-benzylaminopyrrolizidin-3-one
  作者：Nicole Langlois、Marie-Odile Radom

  DOI：10.1016/s0040-4039(97)10749-3

  日期：1998.2

  The highly stereoselective synthesis of of (2S,3S)-3N-benzylaminoprolinol and derivatives involved the conjugate addition of N-benzylamine to alpha,beta-unsaturated lactam 2. Wittig-Horner reactions with 1-acetyl-3-N-acetyl-N-benzylaminoprolinal provided a simple access to (7S,8R)-7-N-benzylaminopyrrolizidin-3-one. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.