2,2-dimethylpropane-1,3-diyl [4-bromo-naphthalenyl] boronate | 884010-18-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,2-dimethylpropane-1,3-diyl [4-bromo-naphthalenyl] boronate
• 英文别名: 2-(4-Bromo-1-naphthyl)-5,5-dimethyl-1,3,2-dioxaborinane；2-(4-bromonaphthalen-1-yl)-5,5-dimethyl-1,3,2-dioxaborinane
• CAS: 884010-18-8
• 化学式: C₁₅H₁₆BBrO₂
• 分子量: 319.006
• InChiKey: XURPLAZLXJZCAJ-UHFFFAOYSA-N

物化性质

• 沸点：
  425.1±28.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.37
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2-dimethylpropane-1,3-diyl [4-bromo-naphthalenyl] boronate 在 bis-triphenylphosphine-palladium(II) chloride 甲醇 、 copper(l) iodide 、 potassium carbonate 、 二乙胺 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.42h， 生成 2,2-dimethylpropane-1,3-diyl [4-ethynyl-naphthalenyl] boronate
  参考文献：
  名称：

  Microwave-assisted synthesis of ethynylarylboronates for the construction of boronic acid-based fluorescent sensors for carbohydrates

  摘要：

  A reliable and operationally simple procedure for the synthesis of 2.2-dimethylpropane-1,3-diyl ethynylaryl boronates 4 was developed. The key step is microwave-facilitated selective formation of 2,2-dimethylpropane-1,3-diyl trimethylsilylethynylaryl boronates by Sonogashira reaction front the corresponding bromides. The use of microwave was found to significantly improve the reaction yield and shorten the reaction time. The 2,2-dimethylpropane-1,3-diyl ethynylaryl boronates 4 prepared can be used in the construction of diboronic acid libraries through [2+3] Huisgen cycloaddition for carbohydrate fluorescent sensor development. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.02.012
• 作为产物：
  描述：

  4-溴-1-萘硼酸 、 2,2-二甲基-1,3-丙二醇 以 甲苯 为溶剂， 反应 1.0h， 以100%的产率得到2,2-dimethylpropane-1,3-diyl [4-bromo-naphthalenyl] boronate
  参考文献：
  名称：

  Microwave-assisted synthesis of ethynylarylboronates for the construction of boronic acid-based fluorescent sensors for carbohydrates

  摘要：

  A reliable and operationally simple procedure for the synthesis of 2.2-dimethylpropane-1,3-diyl ethynylaryl boronates 4 was developed. The key step is microwave-facilitated selective formation of 2,2-dimethylpropane-1,3-diyl trimethylsilylethynylaryl boronates by Sonogashira reaction front the corresponding bromides. The use of microwave was found to significantly improve the reaction yield and shorten the reaction time. The 2,2-dimethylpropane-1,3-diyl ethynylaryl boronates 4 prepared can be used in the construction of diboronic acid libraries through [2+3] Huisgen cycloaddition for carbohydrate fluorescent sensor development. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.02.012