pinacol 2,4,6-tribromo-3-hydroxyphenylboronate | 1610366-45-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: pinacol 2,4,6-tribromo-3-hydroxyphenylboronate
• 英文别名: 2,4,6-Tribromo-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol；2,4,6-tribromo-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol
• CAS: 1610366-45-4
• 化学式: C₁₂H₁₄BBr₃O₃
• 分子量: 456.764
• InChiKey: UXQBTVRVOZJLDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.98
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  pinacol 2,4,6-tribromo-3-hydroxyphenylboronate 在 potassium hydroxide 作用下， 以 水 为溶剂， 生成 三溴苯酚
  参考文献：
  名称：

  Base-Promoted Protodeboronation of 2,6-Disubstituted Arylboronic Acids

  摘要：

  Facile based promoted deboronation of electron-deficient arylboronate esters was observed for arylboronates containing two ortho electron-withdrawing group (EWG) substituents. Among 30 representative boronates, only the diortho-substituted species underwent facile C-B fission in aqueous basic conditions (200 mM hydroxide). These results provide fundamental insight into deboronative mechanisms with implications for cross-coupling reactions, regioselective deuteration/tritiation for isotopic labeling, and the design of new F-18-trifluoroborate radioprosthetics.

  DOI：

  10.1021/jo500734z
• 作为产物：
  描述：

  3-羟基苯硼酸 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 以75%的产率得到pinacol 2,4,6-tribromo-3-hydroxyphenylboronate
  参考文献：
  名称：

  用N-卤代琥珀酰亚胺对芳基硼酸酯进行无金属卤化

  摘要：

  无需添加金属试剂即可完成芳基频哪醇硼酸酯的有效溴化和氯化反应。用富电子的芳基硼酸酯或杂芳基硼酸酯在DMF或乙腈中有效地进行反应，得到单，二或三卤代芳基频哪醇硼酸酯。

  DOI：

  10.1016/j.tetlet.2014.06.003

文献信息

• Base-Promoted Protodeboronation of 2,6-Disubstituted Arylboronic Acids
  作者：Jerome Lozada、Zhibo Liu、David M. Perrin

  DOI：10.1021/jo500734z

  日期：2014.6.6

  Facile based promoted deboronation of electron-deficient arylboronate esters was observed for arylboronates containing two ortho electron-withdrawing group (EWG) substituents. Among 30 representative boronates, only the diortho-substituted species underwent facile C-B fission in aqueous basic conditions (200 mM hydroxide). These results provide fundamental insight into deboronative mechanisms with implications for cross-coupling reactions, regioselective deuteration/tritiation for isotopic labeling, and the design of new F-18-trifluoroborate radioprosthetics.
• Metal-free halogenation of arylboronate with N-halosuccinimide
  作者：Toshiyuki Kamei、Aoi Ishibashi、Toyoshi Shimada

  DOI：10.1016/j.tetlet.2014.06.003

  日期：2014.7

  Efficient bromination and chlorination of aryl pinacol boronates were accomplished without the addition of metal reagent. The reaction proceeded efficiently with electron-rich arylboronates or heteroarylboronates in DMF or acetonitrile, to afford mono-, di-, or trihalogenated aryl pinacol boronates.

  无需添加金属试剂即可完成芳基频哪醇硼酸酯的有效溴化和氯化反应。用富电子的芳基硼酸酯或杂芳基硼酸酯在DMF或乙腈中有效地进行反应，得到单，二或三卤代芳基频哪醇硼酸酯。