(E)-3,3'-(((4-(5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-en-1-yl)-1,3-phenylene)bis(oxy))bis(methylene))difuran | 1263361-94-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-3,3'-(((4-(5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-en-1-yl)-1,3-phenylene)bis(oxy))bis(methylene))difuran
• CAS: 1263361-94-9
• 化学式: C₂₆H₃₀O₅
• 分子量: 422.521
• InChiKey: STLATBQSTQHAPJ-RMOCHZDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.48
• 重原子数：
  31.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  57.27
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (E)-3,3'-(((4-(5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-en-1-yl)-1,3-phenylene)bis(oxy))bis(methylene))difuran 在 三氟化硼乙醚 作用下， 以 1,1-二氯乙烷 为溶剂， 反应 0.1h， 以49%的产率得到
  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)-3,3'-(((4-(3,7-dimethylocta-2,6-dien-1-yl)-1,3-phenylene)bis(oxy))bis(methylene))difuran 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以41%的产率得到(E)-3,3'-(((4-(5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-en-1-yl)-1,3-phenylene)bis(oxy))bis(methylene))difuran
  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