(5S)-1-methyl-5-isopropyl-2,4-dioxopyrrolidine | 88517-61-7

• 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: (5S)-1-methyl-5-isopropyl-2,4-dioxopyrrolidine
• 英文别名: 5-Isopropyl-1-methylpyrrolidine-2,4-dione；(S)-5-Isopropyl-1-methylpyrrolidine-2,4-dione；(5S)-1-methyl-5-propan-2-ylpyrrolidine-2,4-dione
• CAS: 88517-61-7
• 化学式: C₈H₁₃NO₂
• 分子量: 155.197
• InChiKey: JWYRWJZQVPLMKQ-QMMMGPOBSA-N

物化性质

• 沸点：
  285.7±33.0 °C(Predicted)
• 密度：
  1.071±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (5S)-1-methyl-5-isopropyl-2,4-dioxopyrrolidine 在 sodium tetrahydroborate 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以77%的产率得到(4S,5S)-1-methyl-5-isopropyl-4-hydroxy-2-oxopyrrolidine
  参考文献：
  名称：

  Diastereofacial selectivity in reduction of chiral tetramic acids

  摘要：

  The reduction of (5S)-5-alkyl-2,4-dioxopyrrolidines, so-called tetramic acids, by NaBH4 gives only partial diastereofacial selectivity in the case of the N-substituted analogues 9f-i, unlike the carbamate derivatives 9a-3 which give the reduced cis-pyrrolidinones 10betaa-e. Increasing the steric hindrance of either the N- or C-5-substituents enhances the re-face selectivity. On the other hand, reduction of the heterobicyclic compound 9n leads to a dramatic reversal of the stereoselectivity. Preliminary calculations show that the N-atom of the ring is slightly pyramidalized; the direction of hydride addition could be a consequence of this finding.

  DOI：

  10.1021/jo00072a018
• 作为产物：
  描述：

  N-苄氧羰基-N-甲基-L-缬氨酸 在 盐酸 、 sodium methylate 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 反应 4.0h， 生成 (5S)-1-methyl-5-isopropyl-2,4-dioxopyrrolidine
  参考文献：
  名称：

  Jones, Raymond C. F.; Begley, Michael J.; Peterson, Graeme E., Journal of the Chemical Society. Perkin transactions I, 1990, # 7, p. 1959 - 1968

  摘要：

  DOI：

文献信息

• Diastereofacial selectivity in reduction of chiral tetramic acids
  作者：Nathalie Galeotti、Joel Poncet、Laurent Chiche、Patrick Jouin

  DOI：10.1021/jo00072a018

  日期：1993.9

  The reduction of (5S)-5-alkyl-2,4-dioxopyrrolidines, so-called tetramic acids, by NaBH4 gives only partial diastereofacial selectivity in the case of the N-substituted analogues 9f-i, unlike the carbamate derivatives 9a-3 which give the reduced cis-pyrrolidinones 10betaa-e. Increasing the steric hindrance of either the N- or C-5-substituents enhances the re-face selectivity. On the other hand, reduction of the heterobicyclic compound 9n leads to a dramatic reversal of the stereoselectivity. Preliminary calculations show that the N-atom of the ring is slightly pyramidalized; the direction of hydride addition could be a consequence of this finding.
• Jones, Raymond C. F.; Begley, Michael J.; Peterson, Graeme E., Journal of the Chemical Society. Perkin transactions I, 1990, # 7, p. 1959 - 1968
  作者：Jones, Raymond C. F.、Begley, Michael J.、Peterson, Graeme E.、Sumaria, Suresh

  DOI：——

  日期：——