(E)-(1S,2R,3S)-2-Methoxymethoxy-4,4,11,11-tetramethyl-bicyclo[6.2.1]undec-7-en-3-ol | 200705-04-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-(1S,2R,3S)-2-Methoxymethoxy-4,4,11,11-tetramethyl-bicyclo[6.2.1]undec-7-en-3-ol
• CAS: 200705-04-0
• 化学式: C₁₇H₃₀O₃
• 分子量: 282.423
• InChiKey: NCMMAVWPLHVZLI-YLBTVKKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.52
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (E)-(1S,2R,3S)-2-Methoxymethoxy-4,4,11,11-tetramethyl-bicyclo[6.2.1]undec-7-en-3-ol 在 吡啶 、 4-二甲氨基吡啶 、 四氧化锇 、 sodium dithionite 、 草酰氯 、 四丁基碘化铵 、 二甲基亚砜 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.42h， 生成 Benzoic acid (1S,3R,6S,7R,8S)-6-benzyloxymethoxy-1-(4-methoxy-benzyloxymethoxy)-7-methoxymethoxy-5,5,11,11-tetramethyl-2-oxo-bicyclo[6.2.1]undec-3-yl ester
  参考文献：
  名称：

  Bicyclic Systems Related to Taxol. A Direct Means for Implementing C-2 Oxygenation and Demonstration of the Feasibility of α-Ketol Equilibration in a Fully Oxygenated B-Ring Setting

  摘要：

  The feasibility of alpha-ketol equilibration in a fully oxygenated B-ring setting for the rapid, enantioselective construction of an A/B bicyclic model related to Taxol has been examined. The key elements associated with this successful venture include selection of a proper array of protecting groups for the four hydroxyl groups present, suitable catalysis of the 1,2-pinacol-like shift, and an intrinsic dependence on the thermodynamic stabilities of the two alpha-ketol isomers. The key conversion of 13 to 14 is seen to be unidirectional and consequently to offer useful potential serviceability as more advanced thrusts toward Taxol are mounted.

  DOI：

  10.1021/jo971592f
• 作为产物：
  描述：

  (E)-(1S,2R)-2-Methoxymethoxy-4,4,11,11-tetramethyl-bicyclo[6.2.1]undec-7-en-3-one 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以93%的产率得到(E)-(1S,2R,3S)-2-Methoxymethoxy-4,4,11,11-tetramethyl-bicyclo[6.2.1]undec-7-en-3-ol
  参考文献：
  名称：

  Bicyclic Systems Related to Taxol. A Direct Means for Implementing C-2 Oxygenation and Demonstration of the Feasibility of α-Ketol Equilibration in a Fully Oxygenated B-Ring Setting

  摘要：

  The feasibility of alpha-ketol equilibration in a fully oxygenated B-ring setting for the rapid, enantioselective construction of an A/B bicyclic model related to Taxol has been examined. The key elements associated with this successful venture include selection of a proper array of protecting groups for the four hydroxyl groups present, suitable catalysis of the 1,2-pinacol-like shift, and an intrinsic dependence on the thermodynamic stabilities of the two alpha-ketol isomers. The key conversion of 13 to 14 is seen to be unidirectional and consequently to offer useful potential serviceability as more advanced thrusts toward Taxol are mounted.

  DOI：

  10.1021/jo971592f