(2R,4aR,9aR)-5,7-bis(methoxymethyl)-1,1,4a-trimethyl-3,4,9,9a-tetrahydro-2H-xanthen-2-ol | 1263361-67-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (2R,4aR,9aR)-5,7-bis(methoxymethyl)-1,1,4a-trimethyl-3,4,9,9a-tetrahydro-2H-xanthen-2-ol
• CAS: 1263361-67-6
• 化学式: C₂₀H₃₀O₄
• 分子量: 334.456
• InChiKey: PABKGQVCJFLFKP-MBOZVWFJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 0.15h， 生成 、 (2R,4aR,9aR)-5,7-bis(methoxymethyl)-1,1,4a-trimethyl-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