(2'S,R,R)-(-)-3-[2'-(1-ethyl-1-methoxypropyl)-2-oxobipyrrolidinyl-3-yl]-butanoic acid methyl ester | 263748-70-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2'S,R,R)-(-)-3-[2'-(1-ethyl-1-methoxypropyl)-2-oxobipyrrolidinyl-3-yl]-butanoic acid methyl ester
• 英文别名: methyl (3R)-3-[(3R)-1-[(2S)-2-(3-methoxypentan-3-yl)pyrrolidin-1-yl]-2-oxopyrrolidin-3-yl]butanoate
• CAS: 263748-70-5
• 化学式: C₁₉H₃₄N₂O₄
• 分子量: 354.49
• InChiKey: YIBPQZNPFVTKJQ-OAGGEKHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2'S,R,R)-(-)-3-[2'-(1-ethyl-1-methoxypropyl)-2-oxobipyrrolidinyl-3-yl]-butanoic acid methyl ester 在 lithium hydroxide 、 lithium 作用下， 以 四氢呋喃 、 氨 为溶剂， 生成 (R,R)-(+)-3-(2-oxopyrrodinyl-3-yl)butanoic acid
  参考文献：
  名称：

  Diastereo- and Enantioselective Synthesis of g- and d-Lactams Bearing a Propionic Acid a-Side-Chain via Michael Addition of N-Dialkylamino Lactams to Enoates

  摘要：

  gamma- and- delta-Lactams [(R,R)-5a-e] bearing a propionic acid alpha-side-chain were synthesized in good overall yields (38 - 58 %, two steps) and diastereo- and enantiomeric excesses (de = greater than or equal to 96%, ee = 90 - greater than or equal to 96%) by 1,4-addition of metalated N-dialkylamino lactams [(S)-2a,b] to enoate Michael accepters (3) followed by saponification of the ester group and subsequent removal of the chiral auxiliary by reductive cleavage of the N-N-bond with lithium in liquid ammonia.

  DOI：

  10.3987/com-99-s83
• 作为产物：
  描述：

  巴豆酸甲酯 、 1-[(2S)-2-(3-methoxypentan-3-yl)pyrrolidin-1-yl]pyrrolidin-2-one 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以84%的产率得到(2'S,R,R)-(-)-3-[2'-(1-ethyl-1-methoxypropyl)-2-oxobipyrrolidinyl-3-yl]-butanoic acid methyl ester
  参考文献：
  名称：

  Diastereo- and Enantioselective Synthesis of g- and d-Lactams Bearing a Propionic Acid a-Side-Chain via Michael Addition of N-Dialkylamino Lactams to Enoates

  摘要：

  gamma- and- delta-Lactams [(R,R)-5a-e] bearing a propionic acid alpha-side-chain were synthesized in good overall yields (38 - 58 %, two steps) and diastereo- and enantiomeric excesses (de = greater than or equal to 96%, ee = 90 - greater than or equal to 96%) by 1,4-addition of metalated N-dialkylamino lactams [(S)-2a,b] to enoate Michael accepters (3) followed by saponification of the ester group and subsequent removal of the chiral auxiliary by reductive cleavage of the N-N-bond with lithium in liquid ammonia.

  DOI：

  10.3987/com-99-s83

文献信息

• Diastereo- and Enantioselective Synthesis of g- and d-Lactams Bearing a Propionic Acid a-Side-Chain via Michael Addition of N-Dialkylamino Lactams to Enoates
  作者：Dieter Enders、Pascal Teschner、Gerhard Raabe

  DOI：10.3987/com-99-s83

  日期：——

  gamma- and- delta-Lactams [(R,R)-5a-e] bearing a propionic acid alpha-side-chain were synthesized in good overall yields (38 - 58 %, two steps) and diastereo- and enantiomeric excesses (de = greater than or equal to 96%, ee = 90 - greater than or equal to 96%) by 1,4-addition of metalated N-dialkylamino lactams [(S)-2a,b] to enoate Michael accepters (3) followed by saponification of the ester group and subsequent removal of the chiral auxiliary by reductive cleavage of the N-N-bond with lithium in liquid ammonia.