methyl 2-chloro-2-fluoro-4,4-dimethoxybutanoate | 1610602-37-3

• 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: methyl 2-chloro-2-fluoro-4,4-dimethoxybutanoate
• CAS: 1610602-37-3
• 化学式: C₇H₁₂ClFO₄
• 分子量: 214.621
• InChiKey: KJOYITLCVBOKDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.07
• 重原子数：
  13.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 2-chloro-2-fluoro-4,4-dimethoxybutanoate 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 以100%的产率得到sodium 2-chloro-2-fluoro-4,4-dimethoxybutanoate
  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
• 作为产物：
  描述：

  甲醇 、 methyl 4-acetoxy-4-bromo-2-chloro-2-fluorobutanoate 反应 12.0h， 以46.8%的产率得到methyl 2-chloro-2-fluoro-4,4-dimethoxybutanoate
  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