(1R,5S)-8-(tert-butoxycarbonyl)-8-azabicyclo<3.2.1>octene-2-carboxylic acid isoxazolidide | 172172-53-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (1R,5S)-8-(tert-butoxycarbonyl)-8-azabicyclo<3.2.1>octene-2-carboxylic acid isoxazolidide
• 英文别名: tert-butyl (1R,5S)-2-(1,2-oxazolidine-2-carbonyl)-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylate
• CAS: 172172-53-1
• 化学式: C₁₆H₂₄N₂O₄
• 分子量: 308.378
• InChiKey: RMIMMXZXQPQOHY-DGCLKSJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,5S)-8-(tert-butoxycarbonyl)-8-azabicyclo<3.2.1>octene-2-carboxylic acid isoxazolidide 在 甲基锂 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 以92%的产率得到(1R,5S)-2-acetyl-8-<(1,1-dimethylethoxy)carbonyl>-8-azabicyclo<3.2.1>octa-2-ene
  参考文献：
  名称：

  Enantiospecific Synthesis of (+)- and (−)-Ferruginine from l-Glutamic Acid. Synthesis of Tropanes via Intramolecular Iminium Ion Cyclization

  摘要：

  Iminium ions, generated by decarbonylation of N-benzyl-5-[1-(methoxycarbonyl)-4-oxopentyl]-prolines, prolines, undergo intramolecular cyclization to afford 2,4-disubstituted tropanes in good yields. This transformation is also shown to be a stereospecific reaction. The value of these substituted tropanes has been demonstrated by functional group manipulation, leading to the enantiospecific synthesis of (+)-ferruginine, an alkaloid isolated from Darlinga ferruginea, and its unnatural enantiomer, (-)-ferruginine.

  DOI：

  10.1021/jo9515081
• 作为产物：
  描述：

  methyl (1R,5S)-8-<(1,1-dimethylethoxy)carbonyl>-8-azabicyclo<3.2.1>octa-2-ene-2-carboxylate 在 氢氧化钾 、 三乙胺 、 氯甲酸异丁酯 作用下， 以 异丙醇 为溶剂， 反应 41.5h， 生成 (1R,5S)-8-(tert-butoxycarbonyl)-8-azabicyclo<3.2.1>octene-2-carboxylic acid isoxazolidide
  参考文献：
  名称：

  Enantiospecific Synthesis of (+)- and (−)-Ferruginine from l-Glutamic Acid. Synthesis of Tropanes via Intramolecular Iminium Ion Cyclization

  摘要：

  Iminium ions, generated by decarbonylation of N-benzyl-5-[1-(methoxycarbonyl)-4-oxopentyl]-prolines, prolines, undergo intramolecular cyclization to afford 2,4-disubstituted tropanes in good yields. This transformation is also shown to be a stereospecific reaction. The value of these substituted tropanes has been demonstrated by functional group manipulation, leading to the enantiospecific synthesis of (+)-ferruginine, an alkaloid isolated from Darlinga ferruginea, and its unnatural enantiomer, (-)-ferruginine.

  DOI：

  10.1021/jo9515081