ethyl 4,4-difluoro-3-(triethylsilyl)but-3-enoate | 1415044-05-1

• 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 4,4-difluoro-3-(triethylsilyl)but-3-enoate
• 英文别名: Ethyl 4,4-difluoro-3-triethylsilylbut-3-enoate；ethyl 4,4-difluoro-3-triethylsilylbut-3-enoate
• CAS: 1415044-05-1
• 化学式: C₁₂H₂₂F₂O₂Si
• 分子量: 264.388
• InChiKey: WUULZDAQYWDRNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.14
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 4,4-difluoro-3-(triethylsilyl)but-3-enoate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 0.5h， 以82%的产率得到4,4-difluoro-3-(triethylsilyl)-but-3-en-1-ol
  参考文献：
  名称：

  New approach to 3,3-difluoroallyl alcohol

  摘要：

  A new difluoroalkene with a triethylsilyl group, 4,4-difluoro-3-(triethylsilyl)- but-3-en-1-ol (1), was synthesized as a new building block for 1,1-difluoro-1-alkenes. Treatment of 1 with sodium hydride in the presence of a catalytic amount of p-methoxyphenol induced Si-Csp(2) bond dissociation. Subsequent addition of an aldehyde to the reactive intermediate afforded 3,3-difluoroallyl alcohol (9). The reaction was accelerated by added p-methoxyphenol. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2012.08.001
• 作为产物：
  描述：

  三乙基氯硅烷 在 正丁基锂 、 三甲基氯硅烷 、 sodium hydride 、 二异丙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 生成 ethyl 4,4-difluoro-3-(triethylsilyl)but-3-enoate
  参考文献：
  名称：

  New approach to 3,3-difluoroallyl alcohol

  摘要：

  A new difluoroalkene with a triethylsilyl group, 4,4-difluoro-3-(triethylsilyl)- but-3-en-1-ol (1), was synthesized as a new building block for 1,1-difluoro-1-alkenes. Treatment of 1 with sodium hydride in the presence of a catalytic amount of p-methoxyphenol induced Si-Csp(2) bond dissociation. Subsequent addition of an aldehyde to the reactive intermediate afforded 3,3-difluoroallyl alcohol (9). The reaction was accelerated by added p-methoxyphenol. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2012.08.001

文献信息

• New approach to synthesize β,β-difluorohomoallylic alcohols
  作者：Masaaki Omote、Tatsuya Miake、Atsushi Tarui、Kazuyuki Sato、Itsumaro Kumadaki、Akira Ando

  DOI：10.1016/j.jfluchem.2012.12.011

  日期：2013.3

  Treatment of ethyl 4,4-difluoro-3-(triethylsilyl)but-3-enoate (3) with TBAF in the presence of MS4 angstrom followed by addition of an aromatic aldehyde afforded ethyl (E)-4,4-difluoro-5-hydroxy-5-arylpent-2-enoate (I) that was a versatile intermediate for constructing a stable isostere of peptide or fluorinated sugar molecules. This strategy offers straightforward approach to synthesize such a versatile intermediate (1). (C) 2013 Elsevier B.V. All rights reserved.
• New approach to 3,3-difluoroallyl alcohol
  作者：Masaaki Omote、Tatsuya Miake、Atsushi Tarui、Kazuyuki Sato、John T. Welch、Itsumaro Kumadaki、Akira Ando

  DOI：10.1016/j.jfluchem.2012.08.001

  日期：2012.12

  A new difluoroalkene with a triethylsilyl group, 4,4-difluoro-3-(triethylsilyl)- but-3-en-1-ol (1), was synthesized as a new building block for 1,1-difluoro-1-alkenes. Treatment of 1 with sodium hydride in the presence of a catalytic amount of p-methoxyphenol induced Si-Csp(2) bond dissociation. Subsequent addition of an aldehyde to the reactive intermediate afforded 3,3-difluoroallyl alcohol (9). The reaction was accelerated by added p-methoxyphenol. (C) 2012 Elsevier B.V. All rights reserved.