2,2-dimethylpropane-1,3-diyl [2-trimethylsilylethynylphenyl] boronate | 884010-27-9

• 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 [2-trimethylsilylethynylphenyl] boronate
• 英文别名: 2-[2-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)phenyl]ethynyl-trimethylsilane；2-[2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl]ethynyl-trimethylsilane
• CAS: 884010-27-9
• 化学式: C₁₆H₂₃BO₂Si
• 分子量: 286.254
• InChiKey: PZHSFRZSCIBRHF-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 [2-trimethylsilylethynylphenyl] boronate 在 甲醇 、 potassium carbonate 作用下， 以75%的产率得到2,2-dimethylpropane-1,3-diyl 2-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：

  2-溴苯基硼酸 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 [2-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

• Selective synthesis of unsymmetric dibenzo[a,e]pentalenes by a rhodium-catalysed stitching reaction
  作者：Keisuke Takahashi、Shingo Ito、Ryo Shintani、Kyoko Nozaki

  DOI：10.1039/c6sc04560j

  日期：——

  developed for the synthesis of unsymmetric dibenzo[a,e]pentalenes. The introduction of appropriately sized silyl groups on the starting substrates led to a high crossover selectivity without using an excess amount of either substrate. The present stitching reaction could produce a variety of unsymmetric dibenzo[a,e]pentalene derivatives, including those with electronically different substituents on the

  已经开发了铑催化的2-（甲硅烷基乙炔基）芳基硼酸酯和2-（甲硅烷基乙炔基）芳基溴化物之间的拼接反应，用于合成不对称的二苯并[ a，e ]戊烯。在起始底物上引入适当大小的甲硅烷基基团导致高的交换选择性，而无需使用过量的任一种底物。当前的缝合反应可产生多种不对称的二苯并[ a，e ]戊烯衍生物，包括在稠合的苯环上具有电子上不同的取代基的那些以及杂芳烃稠合的化合物。还证明了脱甲硅烷基化卤化反应可合成相应的卤化二苯并[ a，e戊烯，可用作进一步化学转化的基础。