(1S,8aS,8bS)-1-((R)-1-Hydroxy-ethyl)-8a-methoxy-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid allyl ester | 175891-53-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (1S,8aS,8bS)-1-((R)-1-Hydroxy-ethyl)-8a-methoxy-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid allyl ester
• CAS: 175891-53-9
• 化学式: C₁₇H₂₃NO₅
• 分子量: 321.373
• InChiKey: VKRYWNAGCQXPRC-BPQZFJFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.15
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  76.07
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (1S,8aS,8bS)-1-((R)-1-Hydroxy-ethyl)-8a-methoxy-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid allyl ester 在 四(三苯基膦)钯 、 (+/-)-potassium-<2-ethyl-hexylate> 作用下， 以64%的产率得到Potassium; (1S,8aS,8bS)-1-((R)-1-hydroxy-ethyl)-8a-methoxy-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylate
  参考文献：
  名称：

  Synthesis and antibacterial activity of 4- and 8-methoxy trinems

  摘要：

  The synthesis of all the isomers of 8-methoxy-(9S,10S,12R)-10-(1-hydroxyethyl)-11-oxo-1-azatricyclo-[7.2.0.0(3,8])-undec-2-ene-carboxylates 2 and 4-methoxy-(9R,10S,12R)-10-(1-hydroxyethyl)-11-oxo-1-azatricyclo-[7.2.0.0(3.8)]-undec-2-ene-carboxylates 3 is described. The biological data obtained indicated that the (4S,8S)-4-methoxy derivative (3b) is the best compound in terms of microbiological activity, breadth of spectrum of action and stability to hydrolytic enzymes, namely beta-lactamases.

  DOI：

  10.1016/0960-894x(96)00056-x
• 作为产物：
  描述：

  草酰氯单烯丙酯 在 四丁基氟化铵 、 溶剂黄146 、 三乙胺 、 亚磷酸三乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 xylene 为溶剂， 生成 (1S,8aS,8bS)-1-((R)-1-Hydroxy-ethyl)-8a-methoxy-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid allyl ester
  参考文献：
  名称：

  Synthesis and antibacterial activity of 4- and 8-methoxy trinems

  摘要：

  The synthesis of all the isomers of 8-methoxy-(9S,10S,12R)-10-(1-hydroxyethyl)-11-oxo-1-azatricyclo-[7.2.0.0(3,8])-undec-2-ene-carboxylates 2 and 4-methoxy-(9R,10S,12R)-10-(1-hydroxyethyl)-11-oxo-1-azatricyclo-[7.2.0.0(3.8)]-undec-2-ene-carboxylates 3 is described. The biological data obtained indicated that the (4S,8S)-4-methoxy derivative (3b) is the best compound in terms of microbiological activity, breadth of spectrum of action and stability to hydrolytic enzymes, namely beta-lactamases.

  DOI：

  10.1016/0960-894x(96)00056-x