(1R,2R,4S,5S)-4-acetyl-8-(tert-butoxycarbonyl)-2-(methoxycarbonyl)-8-azabicyclo<3.2.1>octane | 172277-45-1

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 托烷生物碱
• 英文名称: (1R,2R,4S,5S)-4-acetyl-8-(tert-butoxycarbonyl)-2-(methoxycarbonyl)-8-azabicyclo<3.2.1>octane
• 英文别名: 8-O-tert-butyl 2-O-methyl (1R,2R,4S,5S)-4-acetyl-8-azabicyclo[3.2.1]octane-2,8-dicarboxylate
• CAS: 172277-45-1
• 化学式: C₁₆H₂₅NO₅
• 分子量: 311.378
• InChiKey: XORSTIKDVFUPAG-FVCCEPFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R,2R,4S,5S)-4-acetyl-8-(tert-butoxycarbonyl)-2-(methoxycarbonyl)-8-azabicyclo<3.2.1>octane 在 1-氧化-2-巯基吡啶 、 氢氧化钾 、 sodium periodate 、 三甲基氯硅烷 、 苯基氯化硒 、 二甲基硫 、 异丁硫醇 、 甲基锂 、 双(三甲基硅烷基)氨基钾 、 臭氧 、 三乙胺 、 lithium diisopropyl amide 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 乙醚 、 异丙醇 为溶剂， 反应 42.58h， 生成 (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：

  二碳酸二叔丁酯 、 (1R,2R,4S,5S)-4-acetyl-8-benzyl-2-(methoxycarbonyl)-8-azabicyclo<3.2.1>octane 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 3.5h， 以97%的产率得到(1R,2R,4S,5S)-4-acetyl-8-(tert-butoxycarbonyl)-2-(methoxycarbonyl)-8-azabicyclo<3.2.1>octane
  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

文献信息

• Enantiospecific Synthesis of (+)- and (−)-Ferruginine from <scp>l</scp>-Glutamic Acid. Synthesis of Tropanes <i>via</i> Intramolecular Iminium Ion Cyclization
  作者：Andrés S. Hernández、Adrian Thaler、Josep Castells、Henry Rapoport

  DOI：10.1021/jo9515081

  日期：1996.1.1

  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.