allyl-t-butylmethyldisiloxane

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: allyl-t-butylmethyldisiloxane
• 英文别名: Tert-butyl-(tert-butyl-methyl-prop-2-enylsilyl)oxy-methyl-prop-2-enylsilane
• 化学式: C₁₆H₃₄OSi₂
• 分子量: 298.616
• InChiKey: JUSLDGCXWNOBLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.13
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  allylbenzyloxy-t-butylmethylsilane 在 乙酸-D3 作用下， 以 氘代四氢呋喃 、 重水 为溶剂， 生成 benzyl alcohol-d 、 allyl-t-butylmethyldisiloxane
  参考文献：
  名称：

  Alkoxyallylsilanes: Functional Protecting Groups

  摘要：

  Allyl-t-butylmethylsilyl groups were shown to function as alcohol protecting groups whose hydrolytic stability was greater than t-butyldimethylsilyl (TBS) and Si(SiMe3)(3) (sisyl) groups. Pseudo-first-order rate constants for the acidic hydrolysis of primary, benzylic, and secondary allyl-t-butylmethylsilyl ethers in AcOD/THF-d(8)/D2O were determined to be 2.94x10(-3), 8.26x10(-4), and 8.26x10(-4)s(-1) respectively. The regioselectivity of acidic hydrolysis of allylbenzyloxy-t-butylmethylsilane 1 was examined under strong acid (p-TsOH/ CD2Cl2) and weak acid (AcOD/HF-d(8)/D2O) conditions. In both cases, benzyl alcohol was initially produced exclusively from silicon-oxygen bond cleavage: allylic cleavage was only subsequently observed over time. However, the allyl group of the silyl ether could be hydrosilylated. The resulting alkoxy-functionalized disiloxane had greater hydrolytic stability under acidic conditions than the starting alkoxyallyl-t-butylmethylsilane. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)01062-5

文献信息

• Alkoxyallylsilanes: Functional Protecting Groups
  作者：Sonya Balduzzi、Michael A. Brook

  DOI：10.1016/s0040-4020(99)01062-5

  日期：2000.3

  Allyl-t-butylmethylsilyl groups were shown to function as alcohol protecting groups whose hydrolytic stability was greater than t-butyldimethylsilyl (TBS) and Si(SiMe3)(3) (sisyl) groups. Pseudo-first-order rate constants for the acidic hydrolysis of primary, benzylic, and secondary allyl-t-butylmethylsilyl ethers in AcOD/THF-d(8)/D2O were determined to be 2.94x10(-3), 8.26x10(-4), and 8.26x10(-4)s(-1) respectively. The regioselectivity of acidic hydrolysis of allylbenzyloxy-t-butylmethylsilane 1 was examined under strong acid (p-TsOH/ CD2Cl2) and weak acid (AcOD/HF-d(8)/D2O) conditions. In both cases, benzyl alcohol was initially produced exclusively from silicon-oxygen bond cleavage: allylic cleavage was only subsequently observed over time. However, the allyl group of the silyl ether could be hydrosilylated. The resulting alkoxy-functionalized disiloxane had greater hydrolytic stability under acidic conditions than the starting alkoxyallyl-t-butylmethylsilane. (C) 2000 Elsevier Science Ltd. All rights reserved.