(3S,3'R,3a'R,4R,6a'R)-1-benzyl-3'-(4-nitrophenyl)-2-oxo-2',4-diphenyltetrahydrospiro[azetidine-3,4'-pyrrolo[3,4-d]isoxazole]-5'(2'H)-carboxylic acid benzyl ester | 1218934-77-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (3S,3'R,3a'R,4R,6a'R)-1-benzyl-3'-(4-nitrophenyl)-2-oxo-2',4-diphenyltetrahydrospiro[azetidine-3,4'-pyrrolo[3,4-d]isoxazole]-5'(2'H)-carboxylic acid benzyl ester
• 英文别名: benzyl (3R,3aR,4S,4'R,6aR)-1'-benzyl-3-(4-nitrophenyl)-2'-oxo-2,4'-diphenylspiro[3,3a,6,6a-tetrahydropyrrolo[3,4-d][1,2]oxazole-4,3'-azetidine]-5-carboxylate
• CAS: 1218934-77-0
• 化学式: C₄₀H₃₄N₄O₆
• 分子量: 666.733
• InChiKey: BCZMKWAOTRRNQH-YZHFOPMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  50
• 可旋转键数：
  8
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  108
• 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 、 (E)-1-(4-nitrophenyl)-N-phenylmethanimine oxide 以 甲苯 为溶剂， 反应 100.0h， 以40%的产率得到(3S,3'R,3a'R,4R,6a'R)-1-benzyl-3'-(4-nitrophenyl)-2-oxo-2',4-diphenyltetrahydrospiro[azetidine-3,4'-pyrrolo[3,4-d]isoxazole]-5'(2'H)-carboxylic acid benzyl 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