(3S,3a'R,4R,6a'S)-1-benzyl-2-oxo-4-phenyl-6',6a'-dihydrospiro[azetidine-3,4'-pyrrolo[3,4-d]isoxazole]-3',5'(3a'H)-dicarboxylic acid 5'-benzyl 3'-ethyl ester | 1218934-78-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3S,3a'R,4R,6a'S)-1-benzyl-2-oxo-4-phenyl-6',6a'-dihydrospiro[azetidine-3,4'-pyrrolo[3,4-d]isoxazole]-3',5'(3a'H)-dicarboxylic acid 5'-benzyl 3'-ethyl ester
• 英文别名: 5-O-benzyl 3-O-ethyl (3aR,4S,4'R,6aS)-1'-benzyl-2'-oxo-4'-phenylspiro[6,6a-dihydro-3aH-pyrrolo[3,4-d][1,2]oxazole-4,3'-azetidine]-3,5-dicarboxylate
• CAS: 1218934-78-1
• 化学式: C₃₁H₂₉N₃O₆
• 分子量: 539.588
• InChiKey: UZPSUSQIIMTYKB-OHMLLRHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  97.7
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (-)-(3R,4S)-2-benzyl-5-benzyloxycarbonyl-3-phenyl-2,5-diazaspiro[3.4]oct-7-en-1-one 、 硝基乙酸乙酯 在 三乙烯二胺 作用下， 以 氯仿 为溶剂， 反应 65.0h， 以15%的产率得到(3S,3a'R,4R,6a'S)-1-benzyl-2-oxo-4-phenyl-6',6a'-dihydrospiro[azetidine-3,4'-pyrrolo[3,4-d]isoxazole]-3',5'(3a'H)-dicarboxylic acid 5'-benzyl 3'-ethyl 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