(7R,8aR,10aR)-7-hydroxy-2-(methoxymethyl)-8,8,10a-trimethyl-6,7,8a,9-tetrahydro-5H-xanthene-4-carbaldehyde | 1263362-08-8

• 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: (7R,8aR,10aR)-7-hydroxy-2-(methoxymethyl)-8,8,10a-trimethyl-6,7,8a,9-tetrahydro-5H-xanthene-4-carbaldehyde
• CAS: 1263362-08-8
• 化学式: C₁₉H₂₆O₄
• 分子量: 318.413
• InChiKey: LGNBGDUJTVFLMH-GPMSIDNRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (7R,8aR,10aR)-7-hydroxy-2-(methoxymethyl)-8,8,10a-trimethyl-6,7,8a,9-tetrahydro-5H-xanthene-4-carbaldehyde 在 间氯过氧苯甲酸 、 potassium carbonate 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 反应 22.0h， 以98%的产率得到(2R,4aR,9aR)-7-(methoxymethyl)-1,1,4a-trimethyl-3,4,9,9a-tetrahydro-2H-xanthene-2,5-diol
  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：

  2-Bromo-4-(methoxymethyl)-1-(phenylmethoxymethoxy)benzene 在 manganese(IV) oxide 、 正丁基锂 、 四甲基乙二胺 、 三氟化硼乙醚 作用下， 以 hexanes 、 乙醚 、 二氯甲烷 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 58.38h， 生成 (7R,8aR,10aR)-7-hydroxy-2-(methoxymethyl)-8,8,10a-trimethyl-6,7,8a,9-tetrahydro-5H-xanthene-4-carbaldehyde
  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