3-氯-4-(3'-溴苄氧基)苯基硼酸 | 849062-25-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 3-氯-4-(3'-溴苄氧基)苯基硼酸
• 中文别名: 3-氯-4-(3’-溴苄氧基)苯基硼酸；4-(3-溴苄氧基)-3-氯苯硼酸
• 英文名称: 4-(3-Bromo-benzyloxy)-3-chlorophenyl-boronic acid
• 英文别名: (4-((3-Bromobenzyl)oxy)-3-chlorophenyl)boronic acid；[4-[(3-bromophenyl)methoxy]-3-chlorophenyl]boronic acid
• CAS: 849062-25-5
• 化学式: C₁₃H₁₁BBrClO₃
• 分子量: 341.397
• InChiKey: HKBRUUCYKMOURT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.36
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2931900090

反应信息

• 作为反应物：
  描述：

  3-氯-4-(3'-溴苄氧基)苯基硼酸 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-chloro-4-(3-trimethylsilylethynylbenzyloxy)-phenyl] 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.