(R,R)-(+)-3-(2-oxopiperidin-3-yl)butanoic acid | 263748-80-7

• 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,R)-(+)-3-(2-oxopiperidin-3-yl)butanoic acid
• 英文别名: (3R)-3-[(3R)-2-oxopiperidin-3-yl]butanoic acid
• CAS: 263748-80-7
• 化学式: C₉H₁₅NO₃
• 分子量: 185.223
• InChiKey: WLRCLFKGLPOIKI-RNFRBKRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲醇 、 (R,R)-(+)-3-(2-oxopiperidin-3-yl)butanoic acid 在 三甲基氯硅烷 作用下， 以100%的产率得到
  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：

  5-氯代戊酰氯 在 lithium hydroxide 、 lithium 、 sodium hydride 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 氨 为溶剂， 反应 3.0h， 生成 (R,R)-(+)-3-(2-oxopiperidin-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