Methyl [(triethylsilyl)oxy]acetate | 150811-54-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: Methyl [(triethylsilyl)oxy]acetate
• 英文别名: methyl 2-triethylsilyloxyacetate
• CAS: 150811-54-4
• 化学式: C₉H₂₀O₃Si
• 分子量: 204.341
• InChiKey: WOLLQIVILBNCFE-UHFFFAOYSA-N

物化性质

• 沸点：
  204.4±23.0 °C(Predicted)
• 密度：
  0.917±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.18
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Methyl [(triethylsilyl)oxy]acetate 、 三甲基氯硅烷 生成 (E)-1-Methoxy-2-triethylsilanyloxy-1-trimethylsilanyloxy-ethene
  参考文献：
  名称：

  Hattori Kouji, Yamamoto Hisashi, Tetrahedron, 50 (1994) N 10, S 3099-3112

  摘要：

  DOI：
• 作为产物：
  描述：

  羟乙酸甲酯 、 三乙基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以21.0 g的产率得到Methyl [(triethylsilyl)oxy]acetate
  参考文献：
  名称：

  Totally Stereocontrolled Nitrone−Ketene Acetal Based Synthesis of (2S,3S)-N-Benzoyl- and N-Boc-phenylisoserine

  摘要：

  A novel, nitrone-ketene acetal based approach to enantiopure (2S,3S)-N-benzoyl- and N-boc-phenylisoserine has been realized. The convergent approach, which involves the intermediacy of isoxazolidinones, proceeds in up to 59% overall yield and requires only three operations from the starting nitrones.

  DOI：

  10.1021/jo971009v

文献信息

• Highly selective enolization method for heteroatom substituted esters; its application to the ireland ester enolate claisen rearrangement
  作者：Kouji Hattori、Hisashi Yamamoto

  DOI：10.1016/s0040-4020(01)81109-1

  日期：1994.3

  A method for the stereoselective synthesis of silyl ketene acetals from α-siloxy esters, β-hydroxy esters, and α-amino esters is described. Internal quench with excess trimethylsilyl chloride of the lithium enolate at −100 °C, which is generated using a hindered base, LTMP, leads to the selective formation of E-silyl ketene acetal. In contrast, the deprotonation at −100 °C using LHMDS in THF-HMPA (4:1)

  描述了一种由α-甲硅烷氧基酯，β-羟基酯和α-氨基酯立体选择性合成甲硅烷基烯酮缩醛的方法。使用受阻碱LTMP在-100°C下用过量的烯醇锂的三甲基甲硅烷基氯进行内部淬灭，可选择性地形成E-甲硅烷基乙烯酮缩醛。相反，使用LHMDS在THF-HMPA（4：1）中在-100°C进行去质子化，然后用叔丁基二甲基甲硅烷基氯进行处理，可以选择性地得到Z-甲硅烷基烯酮缩醛。该方法可用于爱尔兰酯烯酸酯克莱森重排的立体选择反应。
• Highly selective generation and application of (E)- and (Z)-silyl ketene acetals from .alpha.-hydroxy esters
  作者：Kouji Hattori、Hisashi Yamamoto

  DOI：10.1021/jo00072a005

  日期：1993.9

  A method for the stereoselective synthesis of silyl ketene acetals from a-hydroxy esters is described. Internal quench with excess TMSCI of the lithium enolate at -100-degrees-C, which is generated using a hindered base, LTMP, leads to the selective formation of (E)-silyl ketene acetal. In contrast, the deprotonation at -100-degrees-C using LHMDS in THF-HMPA (4:1), followed by treatment with tert-butyldimethylsilyl chloride affords the (Z)-silyl ketene acetal selectively. The method can be applied to the stereoselective reaction of the Ireland ester enolate Claisen rearrangement and aldol synthesis.