[4-[4,6-Bis[4-(trifluoromethylsulfonyloxy)phenyl]-1,3,5,2,4,6-trioxatriborinan-2-yl]phenyl] trifluoromethanesulfonate | 1287702-12-8

• 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: [4-[4,6-Bis[4-(trifluoromethylsulfonyloxy)phenyl]-1,3,5,2,4,6-trioxatriborinan-2-yl]phenyl] trifluoromethanesulfonate
• 英文别名: [4-[4,6-bis[4-(trifluoromethylsulfonyloxy)phenyl]-1,3,5,2,4,6-trioxatriborinan-2-yl]phenyl] trifluoromethanesulfonate
• CAS: 1287702-12-8
• 化学式: C₂₁H₁₂B₃F₉O₁₂S₃
• 分子量: 755.936
• InChiKey: RLLPMCKGEFLJJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.92
• 重原子数：
  48
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  183
• 氢给体数：
  0
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  [4-[4,6-Bis[4-(trifluoromethylsulfonyloxy)phenyl]-1,3,5,2,4,6-trioxatriborinan-2-yl]phenyl] trifluoromethanesulfonate 在 1,1'-双(二苯基膦)二茂铁 、 potassium fluoride 、 potassium phosphate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 palladium diacetate 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 88.0h， 生成 Methyl 3-[4-[4-[4-[4-[4-chloro-2-(hydroxymethyl)phenyl]phenyl]-2-(hydroxymethyl)phenyl]phenyl]-2-(hydroxymethyl)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-iodophenyl 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52%的产率得到[4-[4,6-Bis[4-(trifluoromethylsulfonyloxy)phenyl]-1,3,5,2,4,6-trioxatriborinan-2-yl]phenyl] 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

• Nickel‐Catalyzed Cross‐Coupling of Bromodifluoromethylphosphonates with Arylboron Reagents
  作者：Masami Kuriyama、Genki Maeda、Kazuya Kamata、Yusuke Kodama、Kosuke Yamamoto、Osamu Onomura

  DOI：10.1002/adsc.202201140

  日期：2023.1.10

  The nickel-catalyzed cross-coupling of bromodifluoromethylphosphonates with arylboron reagents was developed with a 1,10-phenanthroline-type ligand. In this process, functionalized and heterocycle-containing boroxines were found to be suitable partners, and the catalytic modification of biologically active molecules, such as fenofibrate and indomethacin, was also successfully achieved. Furthermore

  溴二氟甲基膦酸酯与芳基硼试剂的镍催化交叉偶联是用 1,10-菲咯啉型配体开发的。在此过程中，发现功能化和含杂环的环硼氧嘧啶是合适的合作伙伴，并成功实现了非诺贝特和吲哚美辛等生物活性分子的催化修饰。此外，克级反应顺利进行，以高产率得到所需产物。
• 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.