Et₃Si(1-oxo-2-pyridinone) | 1526929-10-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: Et₃Si(1-oxo-2-pyridinone)
• 英文别名: Et₃Si(OPO)；1-Triethylsilyloxypyridin-2-one；1-triethylsilyloxypyridin-2-one
• CAS: 1526929-10-1
• 化学式: C₁₁H₁₉NO₂Si
• 分子量: 225.363
• InChiKey: SGKJHJYHKGMHJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.28
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  羟吡啶酮 、 三乙基氯硅烷 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以98%的产率得到Et₃Si(1-oxo-2-pyridinone)
  参考文献：
  名称：

  Chelation and Stereodynamic Equilibria in Neutral Hypercoordinate Organosilicon Complexes of 1-Hydroxy-2-pyridinone

  摘要：

  A series of neutral organosilicon compounds, R3Si(OPO) (R = Me (1), Et (2), Ph (3)), cis-R2Si(OPO)(2) (R = Me (4), Et (5), Pr-i (6), Bu-t (7), Ph (9)), (CH2)(3)Si(OPO)(2) (8), and cis-R2Si(OPO)Cl (R = Me (10), Et (11)) (OPO = 1-oxo-2-pyridinone) have been prepared and fully characterized. X-ray crystallographic analyses show 1 to be tetracoordinate, 3, 7, and 10 to be pentacoordinate, and 4-6, 8, and 9 to be hexacoordinate. In the hexacoordinate structures, a mixture of diastereomers is observed in the form of C/N site disorder in each OPO ligand. Variable-temperature C-13 and Si-29 NMR studies indicate reversible Si <- OC bond, dissociation occurring in all pentacoordinate and hexacoordinate complexes to a varying degree with greater tendency toward dissociation in hydrogen-bonding donor solvents. Significant weakening of the dative Si <- OC bond in 3 is observed in the cocrystallized adduct solvate 3 center dot Ph3SiOH center dot(1)/2C5H12, providing structural evidence for the decrease in coordination number of the OPO ligand by hydrogen-bonding donors. In the hexacoordinate complexes, increasing steric bulk of ancillary ligands also was found to promote dissociation. H-1 and C-13 VT-NMR studies of 4, 6, 8, and 9 indicate stereoisomerization equilibria concurrent with Si <- OC bond dissociation proposed to occur through trigonal-bipyramidal intermediates.

  DOI：

  10.1021/om400907s

文献信息

• Chelation and Stereodynamic Equilibria in Neutral Hypercoordinate Organosilicon Complexes of 1-Hydroxy-2-pyridinone
  作者：Bradley M. Kraft、William W. Brennessel

  DOI：10.1021/om400907s

  日期：2014.1.13

  A series of neutral organosilicon compounds, R3Si(OPO) (R = Me (1), Et (2), Ph (3)), cis-R2Si(OPO)(2) (R = Me (4), Et (5), Pr-i (6), Bu-t (7), Ph (9)), (CH2)(3)Si(OPO)(2) (8), and cis-R2Si(OPO)Cl (R = Me (10), Et (11)) (OPO = 1-oxo-2-pyridinone) have been prepared and fully characterized. X-ray crystallographic analyses show 1 to be tetracoordinate, 3, 7, and 10 to be pentacoordinate, and 4-6, 8, and 9 to be hexacoordinate. In the hexacoordinate structures, a mixture of diastereomers is observed in the form of C/N site disorder in each OPO ligand. Variable-temperature C-13 and Si-29 NMR studies indicate reversible Si <- OC bond, dissociation occurring in all pentacoordinate and hexacoordinate complexes to a varying degree with greater tendency toward dissociation in hydrogen-bonding donor solvents. Significant weakening of the dative Si <- OC bond in 3 is observed in the cocrystallized adduct solvate 3 center dot Ph3SiOH center dot(1)/2C5H12, providing structural evidence for the decrease in coordination number of the OPO ligand by hydrogen-bonding donors. In the hexacoordinate complexes, increasing steric bulk of ancillary ligands also was found to promote dissociation. H-1 and C-13 VT-NMR studies of 4, 6, 8, and 9 indicate stereoisomerization equilibria concurrent with Si <- OC bond dissociation proposed to occur through trigonal-bipyramidal intermediates.