benzyl 2-triphenylsilyl-2-oxoacetate | 443988-58-7

• 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-triphenylsilyl-2-oxoacetate
• 英文别名: Benzyl 2-oxo-2-triphenylsilylacetate
• CAS: 443988-58-7
• 化学式: C₂₇H₂₂O₃Si
• 分子量: 422.555
• InChiKey: GCCLVDHZKJJSGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.01
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzyl 2-triphenylsilyl-2-oxoacetate 在 sodium carbonate 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Synthesis of novel silylated 1,2,4-triazin-5-ones

  摘要：

  The reaction of various alpha-silyl-alpha-keto esters with thiosemicarbazide at 50 degrees C in ethyl acetate was found to give alpha-silyl-substituted thiosemicarbazone-acetic acid esters in good yield. These may then be converted to their corresponding silyl-substituted 1,2,4-triazin-5-ones by cyclization under basic conditions. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.04.021
• 作为产物：
  描述：

  benzyl 2-triphenylsilyl-2-diazoacetate 在 dirhodium tetraacetate 、 methyloxirane 作用下， 以 甲苯 为溶剂， 以81%的产率得到benzyl 2-triphenylsilyl-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