(2-bromo-3,6-dimethoxyphenyl)diphenylphosphine oxide | 136202-04-5

• 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: (2-bromo-3,6-dimethoxyphenyl)diphenylphosphine oxide
• 英文别名: 2-Bromo-3-diphenylphosphoryl-1,4-dimethoxybenzene
• CAS: 136202-04-5
• 化学式: C₂₀H₁₈BrO₃P
• 分子量: 417.239
• InChiKey: NMSYTTKQPSZVKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (2,5-dimethoxyphenyl)diphenylphosphine oxide 在 N-溴代丁二酰亚胺(NBS) 、 叔丁基锂 作用下， 生成 (2-bromo-3,6-dimethoxyphenyl)diphenylphosphine oxide
  参考文献：
  名称：

  Selective ortho lithiation of (2,5-dimethoxyphenyl)diphenylphosphine oxide and trapping of the resulting aryllithium with electrophiles

  摘要：

  The title compound undergoes predominant 6-lithiation, ortho to the methoxy and phosphinoyl groups, on reaction with t-BuLi in THF under conditions of thermodynamic control at low temperature. The organolithium compound is stable at least to 0-degree-C and can be trapped by a range of electrophiles to give the corresponding tetrasubstituted (diphenylphosphinoyl)arenes in moderate to good yield. The iodide formed by this sequence undergoes Ullman coupling to the diphenyl, which exhibits a novel restricted rotation phenomenon, in good yield under mild conditions. (2,5-Dimethoxyphenyl)diphenylphosphine sulfide lithiates exclusively at the 4-position under the same conditions, whilst the corresponding phosphine is unreactive.

  DOI：

  10.1021/jo00024a019