(E)-4,4'-(((4-(3,7-dimethylocta-2,6-dien-1-yl)-1,3-phenylene)bis(oxy))bis(methylene))bis(nitrobenzene) | 1263362-52-2

• 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)-4,4'-(((4-(3,7-dimethylocta-2,6-dien-1-yl)-1,3-phenylene)bis(oxy))bis(methylene))bis(nitrobenzene)
• CAS: 1263362-52-2
• 化学式: C₃₀H₃₂N₂O₆
• 分子量: 516.594
• InChiKey: RUUXCBGIXDOTGW-HCGXMYGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  38.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  104.74
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (E)-4,4'-(((4-(3,7-dimethylocta-2,6-dien-1-yl)-1,3-phenylene)bis(oxy))bis(methylene))bis(nitrobenzene) 在 三氟化硼乙醚 、 间氯过氧苯甲酸 作用下， 以 1,1-二氯乙烷 、 二氯甲烷 为溶剂， 反应 1.13h， 生成 (1S,2R,4R)-2-[[2,4-bis[(4-nitrophenyl)methoxy]phenyl]methyl]-1,3,3-trimethyl-7-oxabicyclo[2.2.1]heptane
  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 、 1-(氯甲基)-4-硝基苯 在 sodium hydride 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 2.33h， 以43%的产率得到(E)-4,4'-(((4-(3,7-dimethylocta-2,6-dien-1-yl)-1,3-phenylene)bis(oxy))bis(methylene))bis(nitrobenzene)
  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