(Z,1S,5S)-2-<<1-(tert-butyldimethylsilyl)oxy>ethylidene>-8-(tert-butoxycarbonyl)-8-azabicyclo<3.2.1>octane | 172172-47-3

• 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: (Z,1S,5S)-2-<<1-(tert-butyldimethylsilyl)oxy>ethylidene>-8-(tert-butoxycarbonyl)-8-azabicyclo<3.2.1>octane
• 英文别名: tert-butyl (1S,2Z,5S)-2-[1-[tert-butyl(dimethyl)silyl]oxyethylidene]-8-azabicyclo[3.2.1]octane-8-carboxylate
• CAS: 172172-47-3
• 化学式: C₂₀H₃₇NO₃Si
• 分子量: 367.604
• InChiKey: NMLBKGCEULJKIS-HHQAHXMXSA-N

物化性质

• 沸点：
  400.4±28.0 °C(predicted)
• 密度：
  0.999±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.84
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z,1S,5S)-2-<<1-(tert-butyldimethylsilyl)oxy>ethylidene>-8-(tert-butoxycarbonyl)-8-azabicyclo<3.2.1>octane 在 苯基氯化硒 、 间氯过氧苯甲酸 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.5h， 生成 (1S,5R)-2-acetyl-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：

  叔丁基二甲基氯硅烷 、 (1S,2S/R,5S)-2-acetyl-8-(tert-butoxycarbonyl)-8-azabicyclo<3.2.1>octane 在 sodium hydride 、 三乙胺 作用下， 生成 (Z,1S,5S)-2-<<1-(tert-butyldimethylsilyl)oxy>ethylidene>-8-(tert-butoxycarbonyl)-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.