methyl trans-1-benzyl-5-oxo-2-phenyl-3-(phenylsulfonyl)-pyrrolidine-3-carboxylate

• 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: methyl trans-1-benzyl-5-oxo-2-phenyl-3-(phenylsulfonyl)-pyrrolidine-3-carboxylate
• 英文别名: methyl (2R,3S)-3-(benzenesulfonyl)-1-benzyl-5-oxo-2-phenylpyrrolidine-3-carboxylate
• 化学式: C₂₅H₂₃NO₅S
• 分子量: 449.527
• InChiKey: RBURIDZEOCHRDT-NOZRDPDXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  89.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl trans-1-benzyl-5-oxo-2-phenyl-3-(phenylsulfonyl)-pyrrolidine-3-carboxylate 在 magnesium 作用下， 以 甲醇 为溶剂， 反应 1.75h， 以76%的产率得到(+/-)-trans-1-benzyl-5-oxo-2-phenylpyrrolidine-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Diastereoselective Synthesis of γ- and δ-Lactams from Imines and Sulfone-Substituted Anhydrides

  摘要：

  Sulfone-substituted gamma- and delta-lactams have been prepared in a single step with high diastereoselectivity. Sulfonylglutaric anhydrides produce intermediates that readily decarboxylate to provide delta-lactams with high diastereoselectivity. Substituents at the 3- or 4-position of the glutaric anhydride induce high levels of stereocontrol. Sulfonylsuccinic anhydrides produce intermediate carboxylic acids that can be trapped as methyl esters or allowed to decarboxylate under mild conditions. This method has been applied to a short synthesis of the pyrrolizidine alkaloid (+/-)-isoretronecanol.

  DOI：

  10.1021/jo500050n
• 作为产物：
  描述：

  苄胺 在 四氢呋喃 、 sodium sulfate 、 原甲酸三乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 生成 methyl trans-1-benzyl-5-oxo-2-phenyl-3-(phenylsulfonyl)-pyrrolidine-3-carboxylate
  参考文献：
  名称：

  Diastereoselective Synthesis of γ- and δ-Lactams from Imines and Sulfone-Substituted Anhydrides

  摘要：

  Sulfone-substituted gamma- and delta-lactams have been prepared in a single step with high diastereoselectivity. Sulfonylglutaric anhydrides produce intermediates that readily decarboxylate to provide delta-lactams with high diastereoselectivity. Substituents at the 3- or 4-position of the glutaric anhydride induce high levels of stereocontrol. Sulfonylsuccinic anhydrides produce intermediate carboxylic acids that can be trapped as methyl esters or allowed to decarboxylate under mild conditions. This method has been applied to a short synthesis of the pyrrolizidine alkaloid (+/-)-isoretronecanol.

  DOI：

  10.1021/jo500050n

文献信息

• Diastereoselective Synthesis of γ- and δ-Lactams from Imines and Sulfone-Substituted Anhydrides
  作者：Nohemy A. Sorto、Michael J. Di Maso、Manuel A. Muñoz、Ryan J. Dougherty、James C. Fettinger、Jared T. Shaw

  DOI：10.1021/jo500050n

  日期：2014.3.21

  Sulfone-substituted gamma- and delta-lactams have been prepared in a single step with high diastereoselectivity. Sulfonylglutaric anhydrides produce intermediates that readily decarboxylate to provide delta-lactams with high diastereoselectivity. Substituents at the 3- or 4-position of the glutaric anhydride induce high levels of stereocontrol. Sulfonylsuccinic anhydrides produce intermediate carboxylic acids that can be trapped as methyl esters or allowed to decarboxylate under mild conditions. This method has been applied to a short synthesis of the pyrrolizidine alkaloid (+/-)-isoretronecanol.