(+)-(5S,6S,7aS)-5-amino-5,6,7,7a-tetrahydro-6-(triisopropylsilyloxy)benzofuran-2(4H)-one | 1365110-02-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: (+)-(5S,6S,7aS)-5-amino-5,6,7,7a-tetrahydro-6-(triisopropylsilyloxy)benzofuran-2(4H)-one
• 英文别名: (5S,6S,7aS)-5-amino-6-tri(propan-2-yl)silyloxy-5,6,7,7a-tetrahydro-4H-1-benzofuran-2-one
• CAS: 1365110-02-6
• 化学式: C₁₇H₃₁NO₃Si
• 分子量: 325.524
• InChiKey: AMCKBVPCEFIAFT-JYJNAYRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.52
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+)-(5S,6S,7aS)-5-amino-5,6,7,7a-tetrahydro-6-(triisopropylsilyloxy)benzofuran-2(4H)-one 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 132.0h， 生成 (+)-N-(but-3-ynyl)-N-((5S,6S,7aS)-2,4,5,6,7,7a-hexahydro-6-(triisopropylsilyloxy)-2-oxobenzofuran-5-yl)formamide
  参考文献：
  名称：

  Asymmetric Total Synthesis of (+)-Virosine A via Sequential Nucleophilic Cyclizations onto an Activated Formamide

  摘要：

  The first synthesis of tetracyclic alkaloid virosine A is reported. The natural alkaloid was prepared in only 13 steps, in an enantioenriched form. The azabicyclo[2.2.2]octane core was efficiently assembled using a key Vilsmeier-Haack and Mannich cyclizations sequence performed in one pot.

  DOI：

  10.1021/jo202651t
• 作为产物：
  描述：

  (+)-(1S,2S,4S,5S)-4-azido-2-hydroxy-5-(triisopropylsilyloxy)cyclohexyl (diethylphosphono)acetate 在 palladium 10% on activated carbon 、 potassium tert-butylate 、 氢气 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 8.0h， 生成 (+)-(5S,6S,7aS)-5-amino-5,6,7,7a-tetrahydro-6-(triisopropylsilyloxy)benzofuran-2(4H)-one
  参考文献：
  名称：

  Asymmetric Total Synthesis of (+)-Virosine A via Sequential Nucleophilic Cyclizations onto an Activated Formamide

  摘要：

  The first synthesis of tetracyclic alkaloid virosine A is reported. The natural alkaloid was prepared in only 13 steps, in an enantioenriched form. The azabicyclo[2.2.2]octane core was efficiently assembled using a key Vilsmeier-Haack and Mannich cyclizations sequence performed in one pot.

  DOI：

  10.1021/jo202651t

文献信息

• Asymmetric Total Synthesis of (+)-Virosine A via Sequential Nucleophilic Cyclizations onto an Activated Formamide
  作者：Guillaume Bélanger、Marianne Dupuis、Robin Larouche-Gauthier

  DOI：10.1021/jo202651t

  日期：2012.4.6

  The first synthesis of tetracyclic alkaloid virosine A is reported. The natural alkaloid was prepared in only 13 steps, in an enantioenriched form. The azabicyclo[2.2.2]octane core was efficiently assembled using a key Vilsmeier-Haack and Mannich cyclizations sequence performed in one pot.