4,4,5,5-四甲基-2-[2-(苯氧基甲基)苯基]-1,3,2-二噁硼烷 | 912569-55-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 4,4,5,5-四甲基-2-[2-(苯氧基甲基)苯基]-1,3,2-二噁硼烷
• 英文名称: 4,4,5,5-Tetramethyl-2-[2-(phenoxymethyl)phenyl]-1,3,2-dioxaborolane
• CAS: 912569-55-2
• 化学式: C₁₉H₂₃BO₃
• 分子量: 310.201
• InChiKey: DTPMFYHICLWUGJ-UHFFFAOYSA-N

物化性质

• 沸点：
  433.6±28.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.56
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-溴乙基基苯硼酸频哪醇酯 、 苯酚 在 四丁基溴化铵 、 potassium carbonate 、 sodium hydroxide 作用下， 反应 0.08h， 以46%的产率得到4,4,5,5-四甲基-2-[2-(苯氧基甲基)苯基]-1,3,2-二噁硼烷
  参考文献：
  名称：

  Microwave-Mediated Synthesis of an Arylboronate Library

  摘要：

  A series of arylboronates has been synthesized from the reaction of 2-(2-, (3-, or (4-(bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 1{1-3) respectively with a range of N-, S-, and O-nucleophiles, using microwave-mediated chemistry. For the synthesis of N- and S-substituted boronates, a supported base, PS-NMM, was employed, and many reactions were complete within 15 min. With O-nucleophiles, a mixture of tetrabutylammonium bromide, potassium carbonate, and sodium hydroxide was employed. The resulting aminomethyl, mercaptomethyl, or alkoxy-/phenoxymethyl-arylboronates were subjected to microwave-mediated Suzuki Miyaura coupling reactions to afford a range of biaryls in moderate to good yields. The X-ray structures of five boronates were determined.

  DOI：

  10.1021/co100011g

文献信息

• Microwave-Mediated Synthesis of an Arylboronate Library
  作者：John Spencer、Christine B. Baltus、Hiren Patel、Neil J. Press、Samantha K. Callear、Louise Male、Simon J. Coles

  DOI：10.1021/co100011g

  日期：2011.1.10

  A series of arylboronates has been synthesized from the reaction of 2-(2-, (3-, or (4-(bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 11-3) respectively with a range of N-, S-, and O-nucleophiles, using microwave-mediated chemistry. For the synthesis of N- and S-substituted boronates, a supported base, PS-NMM, was employed, and many reactions were complete within 15 min. With O-nucleophiles, a mixture of tetrabutylammonium bromide, potassium carbonate, and sodium hydroxide was employed. The resulting aminomethyl, mercaptomethyl, or alkoxy-/phenoxymethyl-arylboronates were subjected to microwave-mediated Suzuki Miyaura coupling reactions to afford a range of biaryls in moderate to good yields. The X-ray structures of five boronates were determined.