(E)-(1S,2R)-2-Methoxymethoxy-4,4,11,11-tetramethyl-bicyclo[6.2.1]undec-7-en-3-one | 200705-03-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-(1S,2R)-2-Methoxymethoxy-4,4,11,11-tetramethyl-bicyclo[6.2.1]undec-7-en-3-one
• 英文别名: (1S,2R,7E)-2-(methoxymethoxy)-4,4,11,11-tetramethylbicyclo[6.2.1]undec-7-en-3-one
• CAS: 200705-03-9
• 化学式: C₁₇H₂₈O₃
• 分子量: 280.408
• InChiKey: STRAYRPWWINJTH-XCEACWERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-(1S,2R)-2-Methoxymethoxy-4,4,11,11-tetramethyl-bicyclo[6.2.1]undec-7-en-3-one 在 吡啶 、 四氧化锇 、 lithium aluminium tetrahydride 、 sodium dithionite 、 四丁基碘化铵 、 N,N-二异丙基乙胺 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.17h， 生成 (1S,2S,6S,7R,8S)-6-Benzyloxymethoxy-7-methoxymethoxy-5,5,11,11-tetramethyl-bicyclo[6.2.1]undecane-1,2-diol
  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：

  (1S,2S,3R,4S)-2-Isopropenyl-3-methoxymethoxy-7,7-dimethyl-1-vinyl-bicyclo[2.2.1]heptan-2-ol 、 碘甲烷 在 18-冠醚-6 、 双(三甲基硅烷基)氨基钾 作用下， 生成 (E)-(1S,2R)-2-Methoxymethoxy-4,4,11,11-tetramethyl-bicyclo[6.2.1]undec-7-en-3-one
  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

文献信息

• 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
  作者：Qingbei Zeng、Simon Bailey、Ting-Zhong Wang、Leo A. Paquette

  DOI：10.1021/jo971592f

  日期：1998.1.1

  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.