(3R,4S,7R)-2-benzyl-7-methanesulfonyloxy-1-oxo-3-phenyl-2,5-diazaspiro[3.4]octane-5-carboxylic acid tert-butyl ester | 1218934-85-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环丁烷
• 英文名称: (3R,4S,7R)-2-benzyl-7-methanesulfonyloxy-1-oxo-3-phenyl-2,5-diazaspiro[3.4]octane-5-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (1R,4S,7R)-2-benzyl-7-methylsulfonyloxy-3-oxo-1-phenyl-2,5-diazaspiro[3.4]octane-5-carboxylate
• CAS: 1218934-85-0
• 化学式: C₂₅H₃₀N₂O₆S
• 分子量: 486.589
• InChiKey: IOJOMEJLCKVGAV-OTPAQWSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3R,4S,7R)-2-benzyl-7-methanesulfonyloxy-1-oxo-3-phenyl-2,5-diazaspiro[3.4]octane-5-carboxylic acid tert-butyl ester 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 反应 3.0h， 以94%的产率得到(3R,4S)-2-benzyl-1-oxo-3-phenyl-2,5-diazaspiro[3.4]oct-7-ene-5-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Enantiomerically Pure Polyheterocyclic Spiro-β-lactams from trans-4-Hydroxy-l-proline

  摘要：

  The "Staudinger ketene-imine reaction" between ketenes generated from natural O,N-protected trans-4-hydroxy-L-prolines and the N-benzyl-N-benzylideneamine led to mixtures of diastereoisomeric, enantiomerically pure pyrrolidine-derived spiro-beta-lactams with a relative cis configuration. These were transformed into the corresponding pyrroline-spiro-beta-lactams by means of treatment with a base and the new C = C double bond Was Submitted to a number of different reactions in order to evaluate its reactivity and obtain new polyheterocyclic enantiomerically pure spiro-beta-lactams.

  DOI：

  10.1021/jo100061s
• 作为产物：
  描述：

  (2S,4r)-1-boc-4-甲磺酰氧基脯氨酸 、 (E)-N-benzylidenebenzylamine 在 2-氯-1-甲基吡啶碘化物 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以45%的产率得到(3R,4S,7R)-2-benzyl-7-methanesulfonyloxy-1-oxo-3-phenyl-2,5-diazaspiro[3.4]octane-5-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Enantiomerically Pure Polyheterocyclic Spiro-β-lactams from trans-4-Hydroxy-l-proline

  摘要：

  The "Staudinger ketene-imine reaction" between ketenes generated from natural O,N-protected trans-4-hydroxy-L-prolines and the N-benzyl-N-benzylideneamine led to mixtures of diastereoisomeric, enantiomerically pure pyrrolidine-derived spiro-beta-lactams with a relative cis configuration. These were transformed into the corresponding pyrroline-spiro-beta-lactams by means of treatment with a base and the new C = C double bond Was Submitted to a number of different reactions in order to evaluate its reactivity and obtain new polyheterocyclic enantiomerically pure spiro-beta-lactams.

  DOI：

  10.1021/jo100061s

文献信息

• Enantiomerically Pure Polyheterocyclic Spiro-β-lactams from <i>trans</i>-4-Hydroxy-<scp>l</scp>-proline
  作者：Giuseppe Cremonesi、Piero Dalla Croce、Francesco Fontana、Concetta La Rosa

  DOI：10.1021/jo100061s

  日期：2010.3.19

  The "Staudinger ketene-imine reaction" between ketenes generated from natural O,N-protected trans-4-hydroxy-L-prolines and the N-benzyl-N-benzylideneamine led to mixtures of diastereoisomeric, enantiomerically pure pyrrolidine-derived spiro-beta-lactams with a relative cis configuration. These were transformed into the corresponding pyrroline-spiro-beta-lactams by means of treatment with a base and the new C = C double bond Was Submitted to a number of different reactions in order to evaluate its reactivity and obtain new polyheterocyclic enantiomerically pure spiro-beta-lactams.