3,4-difluoro-5-hydroxy-5,6-dihydropyran-2-one | 1610602-22-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 3,4-difluoro-5-hydroxy-5,6-dihydropyran-2-one
• 英文别名: 4,5-difluoro-3-hydroxy-2,3-dihydropyran-6-one
• CAS: 1610602-22-6
• 化学式: C₅H₄F₂O₃
• 分子量: 150.082
• InChiKey: YSOXFOBLEOXMRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  methyl 2,3,3-trifluoro-4,5-dihydroxypentanoate 在 对甲苯磺酸 、 三乙胺 作用下， 以 甲苯 、 乙醚 为溶剂， 反应 96.75h， 生成 3,4-difluoro-5-(hydroxymethyl)furan-2(5H)-one 、 3,4-difluoro-5-hydroxy-5,6-dihydropyran-2-one
  参考文献：
  名称：

  Synthesis of 5-alkyl-3,4-difluorofuran-2(5H)-ones by lactonisation. Effects of substituents on cyclisation ability of fluorinated 4-hydroxyalkanoates. DFT calculations of the cyclisation energies

  摘要：

  5-Alkyl-3,4-difluorofuran-2(5H)-ones were synthesised starting with radical addition of ethers to methyl 2,3,3-trifluoroprop-2-enoate, followed by alkyloxy bond cleavage, acid-catalyzed lactonisation and dehydrofluorination. For a study of substituent effects on lactonisation, methyl 4-bromo-2-chloro-2-fluorodecanoate and 2-chloro-2-fluoro-4,4-dimethoxybutanoate based on radical additions of methyl 2-bromo-2-chloro-2-fluoroacetate to oct-1-ene or vinyl acetate were prepared. DFT calculations of the transition state energies of the exo-trig cyclisations confirmed the observation that the ring closure became more feasible with increasing number of alkyls at C4 of the fluorinated 4-hydroxyesters. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2014.03.009