ethyl 4-methyl-3-(fluorodiphenylsilyl)pentanoate | 627878-59-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 4-methyl-3-(fluorodiphenylsilyl)pentanoate
• 英文别名: Ethyl 3-[fluoro(diphenyl)silyl]-4-methylpentanoate
• CAS: 627878-59-5
• 化学式: C₂₀H₂₅FO₂Si
• 分子量: 344.501
• InChiKey: KVNAUNLQOVIODP-UHFFFAOYSA-N

物化性质

• 沸点：
  403.2±37.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 4-methyl-3-(fluorodiphenylsilyl)pentanoate 在 甲醇 、 N,N-二甲基丙烯基脲 、 锂硼氢 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 18.0h， 生成 (3RS,4SR)-1-oxa-3-(1-methylethyl)-5-ethoxy-4-methyl-2,2-diphenyl-2-silacyclopentane
  参考文献：
  名称：

  Use of an Aminosilyllithium for the Diastereoselective Synthesis of Diphenyl Oxasilacyclopentane Acetals and Polyols

  摘要：

  The conjugate addition reaction of a stable, in situ generated silyllithium gives a beta-hydroxysilyl ester with high diastereoselectivity. Conversion of the beta-hydroxysilyl ester to a beta-fluorosilyl ester affords the precursor to the oxasilacyclopentane acetal in high yields under mild conditions. A hydride reduction and subsequent intramolecular silylation lead to the acetal in excellent yields. Finally, highly selective nucleophilic substitution affords oxasilacyclopentanes, which undergo a mild oxidation to afford 1,3-trans diols with high selectivity.

  DOI：

  10.1021/ol035577a
• 作为产物：
  描述：

  chloro(N,N-diethylamino)diphenylsilane 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 ethyl 4-methyl-3-(fluorodiphenylsilyl)pentanoate
  参考文献：
  名称：

  Use of an Aminosilyllithium for the Diastereoselective Synthesis of Diphenyl Oxasilacyclopentane Acetals and Polyols

  摘要：

  The conjugate addition reaction of a stable, in situ generated silyllithium gives a beta-hydroxysilyl ester with high diastereoselectivity. Conversion of the beta-hydroxysilyl ester to a beta-fluorosilyl ester affords the precursor to the oxasilacyclopentane acetal in high yields under mild conditions. A hydride reduction and subsequent intramolecular silylation lead to the acetal in excellent yields. Finally, highly selective nucleophilic substitution affords oxasilacyclopentanes, which undergo a mild oxidation to afford 1,3-trans diols with high selectivity.

  DOI：

  10.1021/ol035577a