B-2-(1-trimethylsilyl-1-hexyl)-1,3,2-dioxaborinane | 612841-95-9

• 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: B-2-(1-trimethylsilyl-1-hexyl)-1,3,2-dioxaborinane
• 英文别名: 1-(1,3,2-Dioxaborinan-2-yl)hexyl-trimethylsilane
• CAS: 612841-95-9
• 化学式: C₁₂H₂₇BO₂Si
• 分子量: 242.242
• InChiKey: ZIIDQRCJXYEDLN-UHFFFAOYSA-N

物化性质

• 沸点：
  275.9±23.0 °C(Predicted)
• 密度：
  0.86±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.74
• 重原子数：
  16
• 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：

  B-2-(1-trimethylsilyl-1-hexyl)-1,3,2-dioxaborinane 在 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以80%的产率得到(+/-)-1-hexyl-1-(trimethylsilyl)methanol
  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：

  1-三甲基硅烷-1-己炔 在 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 、 正戊烷 为溶剂， 反应 15.5h， 生成 B-2-(1-trimethylsilyl-1-hexyl)-1,3,2-dioxaborinane
  参考文献：
  名称：

  A simple synthesis of B-2-(1-trimethylsilyl-1-alkyl)-1,3,2-dioxaborinanes. Isolation and selective oxidation to 1-trimethylsilyl-1-alkanols

  摘要：

  (Z)-1-Trimethylsilyl-1-alkenes easily prepared by the hydroboration of the corresponding 1-trimethylsilyl-1-alkynes followed by protonolysis with acetic acid, readily react with dibromoborane-methyl sulfide complex in dichloromethane for 6 h. The resulting solution is then treated with 1,3-propane diol in a 1:1 mixture of dichloromethane and n-pentane at 0degreesC 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 trimethylsilyl group. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01750-7

文献信息

• A simple synthesis of B-2-(1-trimethylsilyl-1-alkyl)-1,3,2-dioxaborinanes. Isolation and selective oxidation to 1-trimethylsilyl-1-alkanols
  作者：Narayan G. Bhat、Amanda Garza

  DOI：10.1016/s0040-4039(03)01750-7

  日期：2003.9

  (Z)-1-Trimethylsilyl-1-alkenes easily prepared by the hydroboration of the corresponding 1-trimethylsilyl-1-alkynes followed by protonolysis with acetic acid, readily react with dibromoborane-methyl sulfide complex in dichloromethane for 6 h. The resulting solution is then treated with 1,3-propane diol in a 1:1 mixture of dichloromethane and n-pentane at 0degreesC 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 trimethylsilyl group. (C) 2003 Elsevier Ltd. All rights reserved.
• 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.