[4-[4,6-Bis[3-methoxy-4-(trifluoromethylsulfonyloxy)phenyl]-1,3,5,2,4,6-trioxatriborinan-2-yl]-2-methoxyphenyl] trifluoromethanesulfonate | 1287702-34-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: [4-[4,6-Bis[3-methoxy-4-(trifluoromethylsulfonyloxy)phenyl]-1,3,5,2,4,6-trioxatriborinan-2-yl]-2-methoxyphenyl] trifluoromethanesulfonate
• CAS: 1287702-34-4
• 化学式: C₂₄H₁₈B₃F₉O₁₅S₃
• 分子量: 846.015
• InChiKey: XQGDQVUKKUOYQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.95
• 重原子数：
  54
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  211
• 氢给体数：
  0
• 氢受体数：
  24

反应信息

• 作为反应物：
  描述：

  Methyl 3-[4-chloro-2-(hydroxymethyl)phenyl]benzoate 、 [4-[4,6-Bis[3-methoxy-4-(trifluoromethylsulfonyloxy)phenyl]-1,3,5,2,4,6-trioxatriborinan-2-yl]-2-methoxyphenyl] trifluoromethanesulfonate 在 potassium phosphate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 22.0h， 以91%的产率得到Methyl 3-[2-(hydroxymethyl)-4-[3-methoxy-4-(trifluoromethylsulfonyloxy)phenyl]phenyl]benzoate
  参考文献：
  名称：

  A Repetitive One-Step Method for Oligoarene Synthesis Using Catalyst-Controlled Chemoselective Cross-Coupling

  摘要：

  A method far oligoarene synthesis involving chemoselective cross-coupling as the key reaction was developed. Boronic acids with a chloro or trifluoromethanesulfonyloxy group were used as the monomer precursors with either of two chemoselective catalytic systems: Pd with P(t-Bu)(3), and Pd with 1,1'-bis(diphenylphosphino)ferrocene (DPPF). This method enabled elongation by one benzene unit in every step and thus reduced the number of steps required for elongation of oligoarene chains with well-defined lengths and sequences of substituted benzene rings.

  DOI：

  10.1021/ol200676k
• 作为产物：
  描述：

  4-iodo-2-methoxyphenyl trifluoromethanesulfonate 在 异丙基氯化镁 、 硼酸三异丙酯 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 以42%的产率得到[4-[4,6-Bis[3-methoxy-4-(trifluoromethylsulfonyloxy)phenyl]-1,3,5,2,4,6-trioxatriborinan-2-yl]-2-methoxyphenyl] trifluoromethanesulfonate
  参考文献：
  名称：

  A Repetitive One-Step Method for Oligoarene Synthesis Using Catalyst-Controlled Chemoselective Cross-Coupling

  摘要：

  A method far oligoarene synthesis involving chemoselective cross-coupling as the key reaction was developed. Boronic acids with a chloro or trifluoromethanesulfonyloxy group were used as the monomer precursors with either of two chemoselective catalytic systems: Pd with P(t-Bu)(3), and Pd with 1,1'-bis(diphenylphosphino)ferrocene (DPPF). This method enabled elongation by one benzene unit in every step and thus reduced the number of steps required for elongation of oligoarene chains with well-defined lengths and sequences of substituted benzene rings.

  DOI：

  10.1021/ol200676k

文献信息

• A Repetitive One-Step Method for Oligoarene Synthesis Using Catalyst-Controlled Chemoselective Cross-Coupling
  作者：Kei Manabe、Mai Ohba、Yuji Matsushima

  DOI：10.1021/ol200676k

  日期：2011.5.6

  A method far oligoarene synthesis involving chemoselective cross-coupling as the key reaction was developed. Boronic acids with a chloro or trifluoromethanesulfonyloxy group were used as the monomer precursors with either of two chemoselective catalytic systems: Pd with P(t-Bu)(3), and Pd with 1,1'-bis(diphenylphosphino)ferrocene (DPPF). This method enabled elongation by one benzene unit in every step and thus reduced the number of steps required for elongation of oligoarene chains with well-defined lengths and sequences of substituted benzene rings.