(3R)-3-[(E)-5-[5-(methoxymethyl)-2-(phenylmethoxymethoxy)phenyl]-3-methylpent-3-enyl]-2,2-dimethyloxirane | 1263362-04-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3R)-3-[(E)-5-[5-(methoxymethyl)-2-(phenylmethoxymethoxy)phenyl]-3-methylpent-3-enyl]-2,2-dimethyloxirane
• CAS: 1263362-04-4
• 化学式: C₂₆H₃₄O₄
• 分子量: 410.554
• InChiKey: YBDUMGVTYMMCIC-HYVVJVNOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R)-3-[(E)-5-[5-(methoxymethyl)-2-(phenylmethoxymethoxy)phenyl]-3-methylpent-3-enyl]-2,2-dimethyloxirane 在 manganese(IV) oxide 、 三氟化硼乙醚 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 65.13h， 生成 (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：

  对羟基苯甲酸甲酯 在 锂硼氢 、 正丁基锂 、 四甲基乙二胺 、 溴 、 sodium hydride 作用下， 以 四氢呋喃 、 hexanes 、 乙醚 、 二氯甲烷 、 mineral oil 为溶剂， 反应 83.92h， 生成 (3R)-3-[(E)-5-[5-(methoxymethyl)-2-(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.