Ethyl 6-[tert-butyl(dimethyl)silyl]oxy-3-oxooctanoate | 845647-54-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: Ethyl 6-[tert-butyl(dimethyl)silyl]oxy-3-oxooctanoate
• 英文别名: ethyl 6-[tert-butyl(dimethyl)silyl]oxy-3-oxooctanoate
• CAS: 845647-54-3
• 化学式: C₁₆H₃₂O₄Si
• 分子量: 316.513
• InChiKey: MTLKFTDUTKCRFO-UHFFFAOYSA-N

物化性质

• 沸点：
  352.3±22.0 °C(Predicted)
• 密度：
  0.942±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.09
• 重原子数：
  21
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Ethyl 6-[tert-butyl(dimethyl)silyl]oxy-3-oxooctanoate 在 二异丁基氢化铝 、 potassium carbonate 、 zinc(II) iodide 作用下， 以 甲苯 为溶剂， 反应 15.0h， 生成 (+)-(E,R_S)-1-(p-tolylsulfinyl)-7-(tert-butyldimethylsilyloxy)-2-nonene-4-one
  参考文献：
  名称：

  Preparation of enantiomerically pure (E)-β-sulfinylenones from β-ketoesters

  摘要：

  Enantiomerically pure (E)-beta-sulfinylenones are smoothly prepared from beta-ketoesters in three steps with good overall yield. Since they can be the substrates of many diastereoselective reactions, they represent versatile precursors of a wide range of chiral building blocks. We propose a rationale to explain the formation of (E)-beta-sulfinylen ones from the corresponding delta-enol-methylethers. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.06.151
• 作为产物：
  描述：

  γ-己内酯 在 四丁基氟化铵 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 Ethyl 6-[tert-butyl(dimethyl)silyl]oxy-3-oxooctanoate
  参考文献：
  名称：

  Ring-opening of lactones with enolate nucleophiles: a simple access to functionalised β-ketoesters, β,δ-diketoesters and β-ketosulfoxides

  摘要：

  gamma-, delta- and epsilon-Lactones are readily opened by stabilised carbanions to the corresponding bis- or tris-silyl ethers, which can be selectively cleaved to 5- 6- or 7-silyloxy-3-ketoesters, 3,5-diketoesters, or 2-ketosulfoxides. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.11.135

文献信息

• Ring-opening of lactones with enolate nucleophiles: a simple access to functionalised β-ketoesters, β,δ-diketoesters and β-ketosulfoxides
  作者：Steve Lanners、Naïma Khiri、Guy Solladié、Gilles Hanquet

  DOI：10.1016/j.tetlet.2004.11.135

  日期：2005.1

  gamma-, delta- and epsilon-Lactones are readily opened by stabilised carbanions to the corresponding bis- or tris-silyl ethers, which can be selectively cleaved to 5- 6- or 7-silyloxy-3-ketoesters, 3,5-diketoesters, or 2-ketosulfoxides. (C) 2004 Elsevier Ltd. All rights reserved.
• Preparation of enantiomerically pure (E)-β-sulfinylenones from β-ketoesters
  作者：Naïma Khiri、Amandine Lefranc、Guy Solladié、Gilles Hanquet

  DOI：10.1016/j.tetlet.2005.06.151

  日期：2005.8

  Enantiomerically pure (E)-beta-sulfinylenones are smoothly prepared from beta-ketoesters in three steps with good overall yield. Since they can be the substrates of many diastereoselective reactions, they represent versatile precursors of a wide range of chiral building blocks. We propose a rationale to explain the formation of (E)-beta-sulfinylen ones from the corresponding delta-enol-methylethers. (c) 2005 Elsevier Ltd. All rights reserved.