(E)-3-(5-(2,4-bis(allyloxy)phenyl)-3-methylpent-3-en-1-yl)-2,2-dimethyloxirane | 1263361-88-1

• 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-(5-(2,4-bis(allyloxy)phenyl)-3-methylpent-3-en-1-yl)-2,2-dimethyloxirane
• CAS: 1263361-88-1
• 化学式: C₂₂H₃₀O₃
• 分子量: 342.478
• InChiKey: NWLNZXKYJATOLQ-CAOOACKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.26
• 重原子数：
  25.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  30.99
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (E)-3-(5-(2,4-bis(allyloxy)phenyl)-3-methylpent-3-en-1-yl)-2,2-dimethyloxirane 在 间氯过氧苯甲酸 作用下， 以 1,1-二氯乙烷 为溶剂， 反应 0.17h， 以33%的产率得到(1SR,2RS,4RS)-2-(2,4-bis(allyloxy)benzyl)-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)-2,4-bis(allyloxy)-1-(3,7-dimethylocta-2,6-dien-1-yl)benzene 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以40%的产率得到(E)-3-(5-(2,4-bis(allyloxy)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

文献信息

• Electrophilic aromatic prenylation via cascade cyclization
  作者：John G. Kodet、Joseph J. Topczewski、Kevyn D. Gardner、David F. Wiemer

  DOI：10.1016/j.tet.2013.08.056

  日期：2013.11

  To gain access to prenylated hexahydroxanthenes, tandem cascade cyclization-electrophilic aromatic substitution reactions have been studied on substrates bearing allylic and propargylic substituents. Both BF3 center dot OEt2 and TMSOTf can be used to initiate this reaction sequence, resulting in different ratios of the C-2 and C-6 substitution products. Even though allylic transposition is observed in some cases, the results of a crossover experiment are consistent with an intramolecular reaction sequence. Taken together, these studies now allow preparation of either the C-2 or C-6 prenylated hexahydroxanthene products. (C) 2013 Elsevier Ltd. All rights reserved.