(E)-(((((4-(3,7-dimethylocta-2,6-dien-1-yl)-1,3-phenylene)bis(oxy))bis(methylene))bis(oxy))bis(ethane-2,1-diyl))bis(trimethylsilane) | 1263362-35-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (E)-(((((4-(3,7-dimethylocta-2,6-dien-1-yl)-1,3-phenylene)bis(oxy))bis(methylene))bis(oxy))bis(ethane-2,1-diyl))bis(trimethylsilane)
• CAS: 1263362-35-1
• 化学式: C₂₈H₅₀O₄Si₂
• 分子量: 506.874
• InChiKey: CVMVIKWKCPHZJO-DHRITJCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  34.0
• 可旋转键数：
  17.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (E)-(((((4-(3,7-dimethylocta-2,6-dien-1-yl)-1,3-phenylene)bis(oxy))bis(methylene))bis(oxy))bis(ethane-2,1-diyl))bis(trimethylsilane) 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以38%的产率得到2-[[2-[(E)-5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-enyl]-5-(2-trimethylsilylethoxymethoxy)phenoxy]methoxy]ethyl-trimethylsilane
  参考文献：
  名称：

  Exploration of Cascade Cyclizations Terminated by Tandem Aromatic Substitution: Total Synthesis of (+)-Schweinfurthin A

  摘要：

  The termination of epoxide-initiated cascade cyclizations with a range of "protected" phenols is described. When the protecting group can be lost as a stabilized electrophile, the cascade process continues beyond ring closure to afford products which have undergone a tandem electrophilic aromatic substitution. A number of groups have proven viable in this process and the regiochemistry of their substitution reactions has been studied. Application of this methodology in the first total synthesis of (+)-schweinfurthin A, a potent antiproliferative agent, has been achieved.

  DOI：

  10.1021/jo1022102
• 作为产物：
  描述：

  (E)-4-(3,7-dimethylocta-2,6-dienyl)benzene-1,3-diol 、 2-(三甲基硅烷基)乙氧甲基氯 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以90%的产率得到(E)-(((((4-(3,7-dimethylocta-2,6-dien-1-yl)-1,3-phenylene)bis(oxy))bis(methylene))bis(oxy))bis(ethane-2,1-diyl))bis(trimethylsilane)
  参考文献：
  名称：

  Exploration of Cascade Cyclizations Terminated by Tandem Aromatic Substitution: Total Synthesis of (+)-Schweinfurthin A

  摘要：

  The termination of epoxide-initiated cascade cyclizations with a range of "protected" phenols is described. When the protecting group can be lost as a stabilized electrophile, the cascade process continues beyond ring closure to afford products which have undergone a tandem electrophilic aromatic substitution. A number of groups have proven viable in this process and the regiochemistry of their substitution reactions has been studied. Application of this methodology in the first total synthesis of (+)-schweinfurthin A, a potent antiproliferative agent, has been achieved.

  DOI：

  10.1021/jo1022102