(+)-(1S,4S,5S)-4-azido-5-(triisopropylsilyloxy)-2-oxocyclohexyl (diethylphosphono)acetate | 1365110-36-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: (+)-(1S,4S,5S)-4-azido-5-(triisopropylsilyloxy)-2-oxocyclohexyl (diethylphosphono)acetate
• 英文别名: [(1S,4S,5S)-4-azido-2-oxo-5-tri(propan-2-yl)silyloxycyclohexyl] 2-diethoxyphosphorylacetate
• CAS: 1365110-36-6
• 化学式: C₂₁H₄₀N₃O₇PSi
• 分子量: 505.624
• InChiKey: RJVAYCQWZATHIB-IHPCNDPISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.77
• 重原子数：
  33
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (+)-(1S,4S,5S)-4-azido-5-(triisopropylsilyloxy)-2-oxocyclohexyl (diethylphosphono)acetate 在 palladium 10% on activated carbon 、 potassium tert-butylate 、 氢气 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 5.0h， 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
• 作为产物：
  描述：

  ((1S,6S)-(6-Azidocyclohex-3-en-1-yl)oxy)trimethylsilane 在 盐酸 、 叔丁基过氧化氢 、 戴斯-马丁氧化剂 、 molybdenum hexacarbonyl 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 甲苯 、 mineral oil 、 苯 为溶剂， 反应 40.58h， 生成 (+)-(1S,4S,5S)-4-azido-5-(triisopropylsilyloxy)-2-oxocyclohexyl (diethylphosphono)acetate
  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.