[1-(1,3,2-Dioxaborinan-2-yl)-5-methylhexyl]-trimethylsilane | 883562-60-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 英文名称: [1-(1,3,2-Dioxaborinan-2-yl)-5-methylhexyl]-trimethylsilane
• 英文别名: [1-(1,3,2-dioxaborinan-2-yl)-5-methylhexyl]-trimethylsilane
• CAS: 883562-60-5
• 化学式: C₁₃H₂₉BO₂Si
• 分子量: 256.269
• InChiKey: CYCAPGOKLPCDQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.99
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  [1-(1,3,2-Dioxaborinan-2-yl)-5-methylhexyl]-trimethylsilane 在 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 α-trimethylsilyl-5-methyl-1-hexanol
  参考文献：
  名称：

  Facile hydroboration of (Z)-1-trimethylsilyl-1-alkenes with dichloroborane–dioxane complex: An easy access to gem-dimetalloalkanes containing boron and silicon

  摘要：

  (Z)-l-Trimethylsilyl-l-alkenes easily prepared by the hydroboration of the corresponding 1-trimethylsilyi-l-alkynes followed by protonolysis with acetic acid, readily react with dichloroborane-dioxane complex in dichloromethane for 6 h. The resulting solution is then treated with 1,3-propane diol in dichloromethane at 0 degrees C for half an hour to provide the corresponding gem-dimetalloalkanes containing boron and silicon. These alpha-trimethylsilylalkylboronate esters are purified by vacuum distillation in high yields (72-84%) and the structures of these novel intermediates are further confirmed by selective oxidation with alkaline hydrogen peroxide to provide the corresponding alcohols containing alpha-trimethylsilyl group in 78-88% isolated yields. (c) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2005.12.043
• 作为产物：
  描述：

  5-甲基-1-已炔 在 正丁基锂 、 bis(cyclohexanyl)borane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 12.5h， 生成 [1-(1,3,2-Dioxaborinan-2-yl)-5-methylhexyl]-trimethylsilane
  参考文献：
  名称：

  Facile hydroboration of (Z)-1-trimethylsilyl-1-alkenes with dichloroborane–dioxane complex: An easy access to gem-dimetalloalkanes containing boron and silicon

  摘要：

  (Z)-l-Trimethylsilyl-l-alkenes easily prepared by the hydroboration of the corresponding 1-trimethylsilyi-l-alkynes followed by protonolysis with acetic acid, readily react with dichloroborane-dioxane complex in dichloromethane for 6 h. The resulting solution is then treated with 1,3-propane diol in dichloromethane at 0 degrees C for half an hour to provide the corresponding gem-dimetalloalkanes containing boron and silicon. These alpha-trimethylsilylalkylboronate esters are purified by vacuum distillation in high yields (72-84%) and the structures of these novel intermediates are further confirmed by selective oxidation with alkaline hydrogen peroxide to provide the corresponding alcohols containing alpha-trimethylsilyl group in 78-88% isolated yields. (c) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2005.12.043

文献信息

• Facile hydroboration of (Z)-1-trimethylsilyl-1-alkenes with dichloroborane–dioxane complex: An easy access to gem-dimetalloalkanes containing boron and silicon
  作者：Narayan G. Bhat、Mary A. Villanueva

  DOI：10.1016/j.jorganchem.2005.12.043

  日期：2006.3

  (Z)-l-Trimethylsilyl-l-alkenes easily prepared by the hydroboration of the corresponding 1-trimethylsilyi-l-alkynes followed by protonolysis with acetic acid, readily react with dichloroborane-dioxane complex in dichloromethane for 6 h. The resulting solution is then treated with 1,3-propane diol in dichloromethane at 0 degrees C for half an hour to provide the corresponding gem-dimetalloalkanes containing boron and silicon. These alpha-trimethylsilylalkylboronate esters are purified by vacuum distillation in high yields (72-84%) and the structures of these novel intermediates are further confirmed by selective oxidation with alkaline hydrogen peroxide to provide the corresponding alcohols containing alpha-trimethylsilyl group in 78-88% isolated yields. (c) 2006 Elsevier B.V. All rights reserved.