[3-Bromo-4-(phenylmethoxymethoxy)phenyl]methanol | 1263362-61-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: [3-Bromo-4-(phenylmethoxymethoxy)phenyl]methanol
• CAS: 1263362-61-3
• 化学式: C₁₅H₁₅BrO₃
• 分子量: 323.186
• InChiKey: HADGXJODVBEYGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [3-Bromo-4-(phenylmethoxymethoxy)phenyl]methanol 在 manganese(IV) oxide 、 正丁基锂 、 四丙基高钌酸铵 、 四甲基乙二胺 、 三氟化硼乙醚 、 sodium hydride 、 N-甲基吗啉氧化物 、 N,N-二异丙基乙胺 、 间氯过氧苯甲酸 、 potassium hydroxide 作用下， 以 四氢呋喃 、 hexanes 、 乙醚 、 乙醇 、 二氯甲烷 、 mineral oil 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 108.97h， 生成
  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：

  苄基氯甲基醚 在 锂硼氢 、 溴 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 68.5h， 生成 [3-Bromo-4-(phenylmethoxymethoxy)phenyl]methanol
  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