1,11-diphenyl-7-oxo-8-(4-methoxyphenyl)-(6R,9S,10R,11S)-azeto[30,40:2,3]pyrano[4,5-c]pyrazole | 1262218-33-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1,11-diphenyl-7-oxo-8-(4-methoxyphenyl)-(6R,9S,10R,11S)-azeto[30,40:2,3]pyrano[4,5-c]pyrazole
• 英文别名: (1R,2S,5R,11S)-3-(4-methoxyphenyl)-10,11-diphenyl-6-oxa-3,9,10-triazatricyclo[6.3.0.02,5]undec-8-en-4-one
• CAS: 1262218-33-6
• 化学式: C₂₆H₂₃N₃O₃
• 分子量: 425.487
• InChiKey: BFHYDXFIMNUCNO-FQUZAXHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  54.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 silver carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 生成 1,11-diphenyl-7-oxo-8-(4-methoxyphenyl)-(6R,9S,10R,11S)-azeto[30,40:2,3]pyrano[4,5-c]pyrazole
  参考文献：
  名称：

  A novel enantiopure tricyclic β-lactam via stereoselective intramolecular nitrilimine cycloaddition

  摘要：

  Starting from the Staudinger [2+2] cycloaddition between the 1-azadiene 1 and acetoxyacetylketene generated in situ from acetoxyacetyl chloride we developed a seven-step synthesis of the novel azeto[3' 4' 2 3]pyrano[4 5-c]pyrazole skeleton 9 in both racemic and enantiopure forms Silver carbonate treatment of the functionalised hydrazonoyl chloride 7 promoted in situ generation of the corresponding nitrilimine 8 which underwent a clean stereoselective cycloaddition to the target tricyclic beta-lactam 9 The key step of the synthetic pathway leading to enantiopure 9 was the production of the enantiopure ezetidinone (3R 4S)-3 by enzymatic resolution with Amano Lypase PS of the racemic precursor (3S* 4R*)-2 (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tetasy.2010.10.018