3-[(E)-5-[2,4-bis(phenylmethoxymethoxy)phenyl]-3-methylpent-3-enyl]-2,2-dimethyloxirane | 1263361-73-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-[(E)-5-[2,4-bis(phenylmethoxymethoxy)phenyl]-3-methylpent-3-enyl]-2,2-dimethyloxirane
• CAS: 1263361-73-4
• 化学式: C₃₂H₃₈O₅
• 分子量: 502.651
• InChiKey: IKLAFQJWTHFTDY-AFUMVMLFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  37
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  49.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-[(E)-5-[2,4-bis(phenylmethoxymethoxy)phenyl]-3-methylpent-3-enyl]-2,2-dimethyloxirane 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以30%的产率得到(2R,4aR,9aR)-1,1,4a-trimethyl-6-(phenylmethoxymethoxy)-5-(phenylmethoxymethyl)-3,4,9,9a-tetrahydro-2H-xanthen-2-ol
  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 sodium hydride 、 间氯过氧苯甲酸 、 sodium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 1.33h， 生成 3-[(E)-5-[2,4-bis(phenylmethoxymethoxy)phenyl]-3-methylpent-3-enyl]-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

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.