benzyl 2-trimethylsilyl-2-diazoacetate | 443988-46-3

• 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-trimethylsilyl-2-diazoacetate
• 英文别名: Benzyl 2-diazo-2-trimethylsilylacetate
• CAS: 443988-46-3
• 化学式: C₁₂H₁₆N₂O₂Si
• 分子量: 248.357
• InChiKey: LUGOBCHQRDDWDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.28
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  28.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzyl 2-trimethylsilyl-2-diazoacetate 在 dirhodium tetraacetate 、 sodium tetrahydroborate 、 methyloxirane 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 3.0h， 生成 benzyl (+)-2-trimethylsilyl-2-hydroxyacetate
  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：

  三氟甲磺酸三甲基硅酯 、 benzyl diazoacetate 在 N,N-二异丙基乙胺 作用下， 以 乙醚 为溶剂， 以85%的产率得到benzyl 2-trimethylsilyl-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

文献信息

• Intermolecular Rhodium(II)-Catalyzed Reactions with Silicon-Substituted Carbonyl Ylides
  作者：Carsten Bolm、Sandra Saladin、Andrey Kasyan

  DOI：10.1021/ol026987m

  日期：2002.12.1

  [reaction: see text] The Rh(II)-catalyzed reaction of benzyl 2-trialkylsilyl-2-diazoacetates with various acyclic and cyclic ketones affords novel dioxolanones via silicon-substituted carbonyl ylides in up to 98% yield.

  [反应：见正文] 2-甲基三烷基甲硅烷基-2-重氮乙酸苄酯与各种无环和环状酮的Rh（II）催化反应可通过硅取代的羰基化物以高达98％的产率提供新型的二氧戊环酮。