5-bromo-2-[diisopropyl(pyrimidin-2-yl)silyl]-1,3-phenylene bis(2,2-dimethylpropanoate) | 1369625-48-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 5-bromo-2-[diisopropyl(pyrimidin-2-yl)silyl]-1,3-phenylene bis(2,2-dimethylpropanoate)
• 英文别名: [5-Bromo-3-(2,2-dimethylpropanoyloxy)-2-[di(propan-2-yl)-pyrimidin-2-ylsilyl]phenyl] 2,2-dimethylpropanoate；[5-bromo-3-(2,2-dimethylpropanoyloxy)-2-[di(propan-2-yl)-pyrimidin-2-ylsilyl]phenyl] 2,2-dimethylpropanoate
• CAS: 1369625-48-8
• 化学式: C₂₆H₃₇BrN₂O₄Si
• 分子量: 549.58
• InChiKey: NWQCUYRDRKLDLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.53
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  78.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-bromo-2-[diisopropyl(pyrimidin-2-yl)silyl]-1,3-phenylene bis(2,2-dimethylpropanoate) 在 氢氟酸 、 N-碘代丁二酰亚胺 、 silver fluoride 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以90%的产率得到5-bromo-2-iodo-1,3-phenylene bis(2,2-dimethylpropanoate)
  参考文献：
  名称：

  Double-Fold C–H Oxygenation of Arenes Using PyrDipSi: a General and Efficient Traceless/Modifiable Silicon-Tethered Directing Group

  摘要：

  The efficient Pd-catalyzed double-fold C-H oxygenation of arenes into resorcinols using the newly developed 2-pyrimidyldiisopropylsilyl (PyrDipSi) directing group is described. Its use allows for the sequential introduction of OAc and OPiv groups in a one-pot manner to produce orthogonally protected resorcinol derivatives. The PyrDipSi group is superior to the previously developed 2-pyridyldiisopropylsilyl (PyDipSi) group, as it is efficient for monooxygenation of ortho-substituted arenes. Notably, the PyrDipSi group can be easily installed into arene molecules and can be easily removed or modified after the oxygenation reaction.

  DOI：

  10.1021/ja3010545
• 作为产物：
  描述：

  2-(diisopropylsilyl)pyrimidine 在 dirhodium tetraacetate 、 potassium phosphate 、 lithium acetate 、 palladium diacetate 作用下， 以 1,4-二氧六环 、 1,2-二氯乙烷 为溶剂， 反应 110.0h， 生成 5-bromo-2-[diisopropyl(pyrimidin-2-yl)silyl]-1,3-phenylene bis(2,2-dimethylpropanoate)
  参考文献：
  名称：

  Double-Fold C–H Oxygenation of Arenes Using PyrDipSi: a General and Efficient Traceless/Modifiable Silicon-Tethered Directing Group

  摘要：

  The efficient Pd-catalyzed double-fold C-H oxygenation of arenes into resorcinols using the newly developed 2-pyrimidyldiisopropylsilyl (PyrDipSi) directing group is described. Its use allows for the sequential introduction of OAc and OPiv groups in a one-pot manner to produce orthogonally protected resorcinol derivatives. The PyrDipSi group is superior to the previously developed 2-pyridyldiisopropylsilyl (PyDipSi) group, as it is efficient for monooxygenation of ortho-substituted arenes. Notably, the PyrDipSi group can be easily installed into arene molecules and can be easily removed or modified after the oxygenation reaction.

  DOI：

  10.1021/ja3010545