Ethyl (E)-4,4-difluoro-5-(2-fluorophenyl)-5-hydroxypent-2-enoate | 1427269-72-4

• 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: Ethyl (E)-4,4-difluoro-5-(2-fluorophenyl)-5-hydroxypent-2-enoate
• 英文别名: ethyl (E)-4,4-difluoro-5-(2-fluorophenyl)-5-hydroxypent-2-enoate
• CAS: 1427269-72-4
• 化学式: C₁₃H₁₃F₃O₃
• 分子量: 274.24
• InChiKey: UKSWPKUPEHLHON-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  ethyl 4,4-difluoro-3-(triethylsilyl)but-3-enoate 、 2-氟苯甲醛 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以65%的产率得到Ethyl (E)-4,4-difluoro-5-(2-fluorophenyl)-5-hydroxypent-2-enoate
  参考文献：
  名称：

  New approach to synthesize β,β-difluorohomoallylic alcohols

  摘要：

  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.

  DOI：

  10.1016/j.jfluchem.2012.12.011

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.