tri-sec-butoxy-phenyl-silane | 18510-20-8

• 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: tri-sec-butoxy-phenyl-silane
• 英文别名: Tri-sec-butoxy-phenyl-silan；Tri(butan-2-yloxy)-phenylsilane
• CAS: 18510-20-8
• 化学式: C₁₈H₃₂O₃Si
• 分子量: 324.536
• InChiKey: PCDRXIBYKFIRQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.28
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯硅烷 、 丁酮 在 tris(2-pyridylthio)methyl zinc hydride 作用下， 以 氘代苯 为溶剂， 反应 3.5h， 生成 tri-sec-butoxy-phenyl-silane
  参考文献：
  名称：

  Hydrosilylation of Aldehydes and Ketones Catalyzed by a Terminal Zinc Hydride Complex, [κ³-Tptm]ZnH

  摘要：

  Tris(2-pyridylthio)methyl zinc hydride, [kappa(3)-Tptm]ZnH, is an effective catalyst for multiple insertions of carbonyl groups into the Si-H bonds of PhxSiH4-x (x = 1, 2). Specifically, [kappa(3)-Tptm]ZnH catalyzes the insertion of a variety of aldehydes and ketones into the Si-H bonds of PhSiH3 and Ph2SiH2 to afford PhSi[OCH(R)R'](3) and Ph,Si[OCH(R)R'](2), respectively. The mechanism for hydrosilylation is proposed to involve insertion of the carbonyl group into the Zn-H bond to afford an alkoxy species, followed by metathesis with the silane to release the alkoxysilane and regenerate the zinc hydride catalyst. Multiple insertion of prochiral ketones results in the formation of diastereomeric mixtures of alkoxysilanes that can be identified by NMR spectroscopy.

  DOI：

  10.1021/acs.organomet.5b00506

文献信息

• Hydrosilylation of Aldehydes and Ketones Catalyzed by a Terminal Zinc Hydride Complex, [κ³-Tptm]ZnH
  作者：Wesley Sattler、Serge Ruccolo、Mahnaz Rostami Chaijan、Tawfiq Nasr Allah、Gerard Parkin

  DOI：10.1021/acs.organomet.5b00506

  日期：2015.10.12

  Tris(2-pyridylthio)methyl zinc hydride, [kappa(3)-Tptm]ZnH, is an effective catalyst for multiple insertions of carbonyl groups into the Si-H bonds of PhxSiH4-x (x = 1, 2). Specifically, [kappa(3)-Tptm]ZnH catalyzes the insertion of a variety of aldehydes and ketones into the Si-H bonds of PhSiH3 and Ph2SiH2 to afford PhSi[OCH(R)R'](3) and Ph,Si[OCH(R)R'](2), respectively. The mechanism for hydrosilylation is proposed to involve insertion of the carbonyl group into the Zn-H bond to afford an alkoxy species, followed by metathesis with the silane to release the alkoxysilane and regenerate the zinc hydride catalyst. Multiple insertion of prochiral ketones results in the formation of diastereomeric mixtures of alkoxysilanes that can be identified by NMR spectroscopy.