(E)-1-(3,7-dimethylocta-2,6-dien-1-yl)-2,4-bis((2-methoxyethoxy)methoxy)benzene | 1263362-36-2

• 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)-1-(3,7-dimethylocta-2,6-dien-1-yl)-2,4-bis((2-methoxyethoxy)methoxy)benzene
• CAS: 1263362-36-2
• 化学式: C₂₄H₃₈O₆
• 分子量: 422.562
• InChiKey: NBIZUZRIFVPWTE-ZVBGSRNCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.92
• 重原子数：
  30.0
• 可旋转键数：
  17.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (E)-1-(3,7-dimethylocta-2,6-dien-1-yl)-2,4-bis((2-methoxyethoxy)methoxy)benzene 在 三氟化硼乙醚 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.13h， 生成 [3-(2,2-dimethylpropanoyloxymethoxy)-4-[[(1S,2R,4R)-1,3,3-trimethyl-7-oxabicyclo[2.2.1]heptan-2-yl]methyl]phenoxy]methyl 2,2-dimethylpropanoate
  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：

  2-甲氧基乙氧基甲基氯 、 (E)-4-(3,7-dimethylocta-2,6-dienyl)benzene-1,3-diol 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以47%的产率得到(E)-1-(3,7-dimethylocta-2,6-dien-1-yl)-2,4-bis((2-methoxyethoxy)methoxy)benzene
  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