methyl 2,3,3-trifluoro-4-methoxyheptanoate

• 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 2,3,3-trifluoro-4-methoxyheptanoate
• 英文别名: methyl 4-methoxy-2,3,3-trifluoroheptanoate
• 化学式: C₉H₁₅F₃O₃
• 分子量: 228.212
• InChiKey: SFSLXWJYPIVYJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2,3,3-trifluoro-4-methoxyheptanoate 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以73.8%的产率得到methyl 2,3,3-trifluoro-4-hydroxyheptanoate
  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：

  甲丁醚 、 三氟丙烯酸甲酯 在 偶氮二异丁腈 、 过氧化苯甲酰 作用下， 生成 methyl 2,3,3-trifluoro-4-methoxyheptanoate 、 methyl 4-butoxy-2,3,3-trifluoroheptanoate
  参考文献：
  名称：

  除双键外，仲烷氧基烷基的新型重排。叔烷氧基乙基自由基形成中的立体屏蔽

  摘要：

  已经证实，使用氘证实了在最初形成的仲烷氧基乙基自由基R 1 R 2 CH-O-CH-CH 3自由基加成到2,3,3-三氟丙烯酸甲酯的过程中1,3氢转移的参与。标记的添加剂。已获得间接证据，表明仲自由基CH 3（CH 2）n -CH-O-CH 3中的部分1,3-氢转移为伯自由基CH 3（CH 2）n -CH 2 -O-CH 2。叔烷氧基乙基自由基R 1 R 2 C-O-CHR 3 R的初始形成由于空间因素，未在繁殖步骤中观察到4。

  DOI：

  10.1016/s0040-4039(01)02150-5

文献信息

• Novel rearrangement of secondary alkoxyalkyl radicals during addition to a double bond. Steric shielding in the formation of tertiary alkoxyethyl radicals
  作者：Oldřich Paleta、Jan Hajduch、Stanislav Bőhm

  DOI：10.1016/s0040-4039(01)02150-5

  日期：2002.1

  The participation of a 1,3-hydrogen shift in initially formed secondary alkoxyethyl radicals R1R2CH-O-CH-CH3 during their free-radical chain additions to methyl 2,3,3-trifluoroacrylate has been confirmed using a deuterium marked additive. Indirect evidence has been obtained for a partial 1,3-hydrogen shift in secondary radicals CH3(CH2)n-CH-O-CH3 to primary radicals CH3(CH2)n-CH2-O-CH2. Initial formation

  已经证实，使用氘证实了在最初形成的仲烷氧基乙基自由基R 1 R 2 CH-O-CH-CH 3自由基加成到2,3,3-三氟丙烯酸甲酯的过程中1,3氢转移的参与。标记的添加剂。已获得间接证据，表明仲自由基CH 3（CH 2）n -CH-O-CH 3中的部分1,3-氢转移为伯自由基CH 3（CH 2）n -CH 2 -O-CH 2。叔烷氧基乙基自由基R 1 R 2 C-O-CHR 3 R的初始形成由于空间因素，未在繁殖步骤中观察到4。
• 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
  作者：Jan Hajduch、Zdeněk Duda、Jiří Beran、Jaroslav Kvíčala、Oldřich Paleta

  DOI：10.1016/j.jfluchem.2014.03.009

  日期：2014.6

  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.