(4S,5R)-1-acetyl-4-(N-benzyl-N-(1,1-dimethylethoxycarbonyl)amino)-5-(1-methylethoxy)pyrrolidin-2-one | 153616-53-6

• 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: (4S,5R)-1-acetyl-4-(N-benzyl-N-(1,1-dimethylethoxycarbonyl)amino)-5-(1-methylethoxy)pyrrolidin-2-one
• 英文别名: tert-butyl N-[(2R,3S)-1-acetyl-5-oxo-2-propan-2-yloxypyrrolidin-3-yl]-N-benzylcarbamate
• CAS: 153616-53-6
• 化学式: C₂₁H₃₀N₂O₅
• 分子量: 390.48
• InChiKey: CSGSRXZSEGFFES-PKOBYXMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  76.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4S,5R)-1-acetyl-4-(N-benzyl-N-(1,1-dimethylethoxycarbonyl)amino)-5-(1-methylethoxy)pyrrolidin-2-one 在 三氟化硼乙醚 、 二甲胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 (3aS,6aS)-1-Benzyl-tetrahydro-3-oxa-1,4-diaza-pentalene-2,5-dione
  参考文献：
  名称：

  Conjugate addition of amines and thiols to (R)-1-acetyl-5-isopropoxy-3-pyrrolin-2-one; Preparation of enantiopure N-acyliminium ion precursors

  摘要：

  Conjugate addition reactions of amines and thiols to enantiopure (R)-1-acetyl-5-isopropoxy-3-pyrrolin-2-one are shown to proceed with high stereoselectivity. The benzylamine and the benzyl mercaptan adducts were N-deacylated and then treated with Lewis acid to effect N-acyliminium cyclization. This cyclization proceeded smoothly with the benzyl mercaptan adduct. The benzylamine adduct only cyclized after amine protection with the Boc group, but then led to an enantiopure oxazolidinone.

  DOI：

  10.1016/s0957-4166(00)80435-8
• 作为产物：
  描述：

  (R)-1-acetyl-5-isopropoxy-3-pyrrolin-2-one 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 (4S,5R)-1-acetyl-4-(N-benzyl-N-(1,1-dimethylethoxycarbonyl)amino)-5-(1-methylethoxy)pyrrolidin-2-one
  参考文献：
  名称：

  Conjugate addition of amines and thiols to (R)-1-acetyl-5-isopropoxy-3-pyrrolin-2-one; Preparation of enantiopure N-acyliminium ion precursors

  摘要：

  Conjugate addition reactions of amines and thiols to enantiopure (R)-1-acetyl-5-isopropoxy-3-pyrrolin-2-one are shown to proceed with high stereoselectivity. The benzylamine and the benzyl mercaptan adducts were N-deacylated and then treated with Lewis acid to effect N-acyliminium cyclization. This cyclization proceeded smoothly with the benzyl mercaptan adduct. The benzylamine adduct only cyclized after amine protection with the Boc group, but then led to an enantiopure oxazolidinone.

  DOI：

  10.1016/s0957-4166(00)80435-8

文献信息

• Conjugate addition of amines and thiols to (R)-1-acetyl-5-isopropoxy-3-pyrrolin-2-one; Preparation of enantiopure N-acyliminium ion precursors
  作者：Wim-Jan Koot、Henk Hiemstra、W.Nico Speckamp

  DOI：10.1016/s0957-4166(00)80435-8

  日期：1993.8

  Conjugate addition reactions of amines and thiols to enantiopure (R)-1-acetyl-5-isopropoxy-3-pyrrolin-2-one are shown to proceed with high stereoselectivity. The benzylamine and the benzyl mercaptan adducts were N-deacylated and then treated with Lewis acid to effect N-acyliminium cyclization. This cyclization proceeded smoothly with the benzyl mercaptan adduct. The benzylamine adduct only cyclized after amine protection with the Boc group, but then led to an enantiopure oxazolidinone.