(E)-5,5'-(((4-(3,7-dimethylocta-2,6-dien-1-yl)-1,3-phenylene)bis(oxy))bis(methylene))bis(1,2,3-trimethoxybenzene) | 1263362-56-6

• 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)-5,5'-(((4-(3,7-dimethylocta-2,6-dien-1-yl)-1,3-phenylene)bis(oxy))bis(methylene))bis(1,2,3-trimethoxybenzene)
• CAS: 1263362-56-6
• 化学式: C₃₆H₄₆O₈
• 分子量: 606.756
• InChiKey: ZLMCFYGHBPEKRH-DHRITJCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.13
• 重原子数：
  44.0
• 可旋转键数：
  17.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  73.84
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (E)-5,5'-(((4-(3,7-dimethylocta-2,6-dien-1-yl)-1,3-phenylene)bis(oxy))bis(methylene))bis(1,2,3-trimethoxybenzene) 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以34%的产率得到(E)-3-(5-(2,4-bis((3,4,5-trimethoxybenzyl)oxy)phenyl)-3-methylpent-3-en-1-yl)-2,2-dimethyloxirane
  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 、 5-溴甲基-1,2,3-三甲氧基苯 在 15-冠醚-5 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 0.5h， 以65%的产率得到(E)-5,5'-(((4-(3,7-dimethylocta-2,6-dien-1-yl)-1,3-phenylene)bis(oxy))bis(methylene))bis(1,2,3-trimethoxybenzene)
  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