[4-[(E)-5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-enyl]-3-(2,2-dimethylpropanoyloxymethoxy)phenoxy]methyl 2,2-dimethylpropanoate | 1263361-76-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: [4-[(E)-5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-enyl]-3-(2,2-dimethylpropanoyloxymethoxy)phenoxy]methyl 2,2-dimethylpropanoate
• CAS: 1263361-76-7
• 化学式: C₂₈H₄₂O₇
• 分子量: 490.637
• InChiKey: DOAVZUCHUKCHAI-VXLYETTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  35
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  83.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [4-[(E)-5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-enyl]-3-(2,2-dimethylpropanoyloxymethoxy)phenoxy]methyl 2,2-dimethylpropanoate 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 0.13h， 以47%的产率得到[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：

  (E)-4-(3,7-dimethylocta-2,6-dienyl)benzene-1,3-diol 在 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 24.0h， 生成 [4-[(E)-5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-enyl]-3-(2,2-dimethylpropanoyloxymethoxy)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

文献信息

• Exploration of Cascade Cyclizations Terminated by Tandem Aromatic Substitution: Total Synthesis of (+)-Schweinfurthin A
  作者：Joseph J. Topczewski、John G. Kodet、David F. Wiemer

  DOI：10.1021/jo1022102

  日期：2011.2.4

  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.