methyl 1-(4'-methoxy-phenyl)-5-triisopropylsilyloxy-2-oxo-cyclohexan-1-carboxylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: methyl 1-(4'-methoxy-phenyl)-5-triisopropylsilyloxy-2-oxo-cyclohexan-1-carboxylate
• 英文别名: methyl (1R,5S)-1-(4-methoxyphenyl)-2-oxo-5-tri(propan-2-yl)silyloxycyclohexane-1-carboxylate
• 化学式: C₂₄H₃₈O₅Si
• 分子量: 434.648
• InChiKey: MWIDZDZXFZNASE-XUZZJYLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.42
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  methyl 5-hydroxy-2-oxo-cyclohexan-1-carboxylate 在 吡啶 、 咪唑 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 methyl 1-(4'-methoxy-phenyl)-5-triisopropylsilyloxy-2-oxo-cyclohexan-1-carboxylate
  参考文献：
  名称：

  Carbanion Stabilization by Distal Silyloxy Groups. Origin of the High Diastereoselectivity in the Formation of Quaternary Centers with Aryllead(IV) Triacetate Reagents

  摘要：

  [GRAPHICS]Derivatives of methyl 5-hydroxy-2-oxo-1-cyclohexanecarboxylate react with aryllead(IV) reagents in high yield and with wide variation in diastereoselectivity. Ab initio calculations are consistent with a heretofore unrecognized attraction between the carbanionic center of the beta-ketoester intermediate and the distal OSiR3 group. This attractive interaction stabilizes the silyl group in the axial conformation and leads to the excellent trans diastereoselection in the formation of quaternary centers.

  DOI：

  10.1021/ol026863+

文献信息

• Carbanion Stabilization by Distal Silyloxy Groups. Origin of the High Diastereoselectivity in the Formation of Quaternary Centers with Aryllead(IV) Triacetate Reagents
  作者：Joseph P. Konopelski、Jinzhen Lin、Philip J. Wenzel、Hongbo Deng、Gregory I. Elliott、Brian S. Gerstenberger

  DOI：10.1021/ol026863+

  日期：2002.11.1

  [GRAPHICS]Derivatives of methyl 5-hydroxy-2-oxo-1-cyclohexanecarboxylate react with aryllead(IV) reagents in high yield and with wide variation in diastereoselectivity. Ab initio calculations are consistent with a heretofore unrecognized attraction between the carbanionic center of the beta-ketoester intermediate and the distal OSiR3 group. This attractive interaction stabilizes the silyl group in the axial conformation and leads to the excellent trans diastereoselection in the formation of quaternary centers.