2,2-dimethylpropane-1,3-diyl [3-trimethylsilylethynylphenyl] boronate | 884010-26-8

• 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: 2,2-dimethylpropane-1,3-diyl [3-trimethylsilylethynylphenyl] boronate
• 英文别名: 2-[3-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)phenyl]ethynyl-trimethylsilane；2-[3-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl]ethynyl-trimethylsilane
• CAS: 884010-26-8
• 化学式: C₁₆H₂₃BO₂Si
• 分子量: 286.254
• InChiKey: BCGXNSWGQHCDBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.68
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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 [3-trimethylsilylethynylphenyl] boronate 在 甲醇 、 potassium carbonate 作用下， 以78%的产率得到2,2-dimethylpropane-1,3-diyl 3-ethynylphenyl 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：

  3-溴苯硼酸 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 二乙胺 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 1.42h， 生成 2,2-dimethylpropane-1,3-diyl [3-trimethylsilylethynylphenyl] 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

文献信息

• Microwave-assisted synthesis of ethynylarylboronates for the construction of boronic acid-based fluorescent sensors for carbohydrates
  作者：Shi-Long Zheng、Suazette Reid、Na Lin、Binghe Wang

  DOI：10.1016/j.tetlet.2006.02.012

  日期：2006.4

  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.