benzyl 2-dimethyl(phenyl)silyl-2-diazoacetate | 443988-50-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl 2-dimethyl(phenyl)silyl-2-diazoacetate
• CAS: 443988-50-9
• 化学式: C₁₇H₁₈N₂O₂Si
• 分子量: 310.428
• InChiKey: BJXUCENJTIOWNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.56
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  62.7
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  benzyl 2-dimethyl(phenyl)silyl-2-diazoacetate 在 dirhodium tetraacetate 、 methyloxirane 作用下， 以 甲苯 为溶剂， 以85%的产率得到benzyl 2-(dimethyl(phenyl)silyl)-2-oxoacetate
  参考文献：
  名称：

  Synthesis and Use of α-Silyl-Substituted α-Hydroxyacetic Acids

  摘要：

  Rhodium-catalyzed oxygen transfer was used to generate benzyl 2-sifyi-2-oxoacetates in good yields. The hydrogenation of these compounds led to chiral alpha-silyl-substituted a-hydroxyacetic acids. Resolution by means of HPLC using a chiral stationary phase afforded an enantiomerically pure representative of this class of compounds, which was successfully applied as a chiral ligand in an asymmetric aldol-type reaction.

  DOI：

  10.1021/ol025911n
• 作为产物：
  描述：

  benzyl diazoacetate 、 phenyldimethylsilyl trifluoromethanesulfonate 在 N,N-二异丙基乙胺 作用下， 以 乙醚 为溶剂， 以79%的产率得到benzyl 2-dimethyl(phenyl)silyl-2-diazoacetate
  参考文献：
  名称：

  Synthesis and Use of α-Silyl-Substituted α-Hydroxyacetic Acids

  摘要：

  Rhodium-catalyzed oxygen transfer was used to generate benzyl 2-sifyi-2-oxoacetates in good yields. The hydrogenation of these compounds led to chiral alpha-silyl-substituted a-hydroxyacetic acids. Resolution by means of HPLC using a chiral stationary phase afforded an enantiomerically pure representative of this class of compounds, which was successfully applied as a chiral ligand in an asymmetric aldol-type reaction.

  DOI：

  10.1021/ol025911n