(3S,4S)-3-acetyl-1-(4-nitrophenylsulfonyl)-4-phenylpyrrolidine-2-one | 1242516-25-1

• 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: (3S,4S)-3-acetyl-1-(4-nitrophenylsulfonyl)-4-phenylpyrrolidine-2-one
• 英文别名: (3S,4S)-3-acetyl-1-(4-nitrophenyl)sulfonyl-4-phenylpyrrolidin-2-one
• CAS: 1242516-25-1
• 化学式: C₁₈H₁₆N₂O₆S
• 分子量: 388.401
• InChiKey: KDFSAWHFRDKJPU-IAGOWNOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  126
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  乙酰乙酸乙酯 、 (R)-1-(p-nitrobenzenesulfonyl)-2-phenylaziridine 在 sodium hydride 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以64%的产率得到(3S,4S)-3-acetyl-1-(4-nitrophenylsulfonyl)-4-phenylpyrrolidine-2-one
  参考文献：
  名称：

  Lewis Acid Catalyzed Highly Stereoselective Domino-Ring-Opening Cyclization of Activated Aziridines with Enolates: Synthesis of Functionalized Chiral γ-Lactams

  摘要：

  A highly enantio- and diastereoselective Lewis acid catalyzed S(N)2-type ring opening followed by cyclization of aziridines with active methylene carbon nucleophiles to functionalized chiral gamma-lactams in a domino fashion has been developed. gamma-Lactams have been desulfonated and decarboxylated, providing pyrrolidone-3-carboxylate and N-tosylpyrrolidinone derivatives, respectively, in good yields.

  DOI：

  10.1021/jo101004x

文献信息

• Lewis Acid Catalyzed Highly Stereoselective Domino-Ring-Opening Cyclization of Activated Aziridines with Enolates: Synthesis of Functionalized Chiral γ-Lactams
  作者：Manas K. Ghorai、Deo Prakash Tiwari

  DOI：10.1021/jo101004x

  日期：2010.9.17

  A highly enantio- and diastereoselective Lewis acid catalyzed S(N)2-type ring opening followed by cyclization of aziridines with active methylene carbon nucleophiles to functionalized chiral gamma-lactams in a domino fashion has been developed. gamma-Lactams have been desulfonated and decarboxylated, providing pyrrolidone-3-carboxylate and N-tosylpyrrolidinone derivatives, respectively, in good yields.