(perfluoro-2,4,5-trimethyl-1,3-dioxolane)-2-carboxylic acid | 814916-39-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (perfluoro-2,4,5-trimethyl-1,3-dioxolane)-2-carboxylic acid
• 英文别名: 2,4,5-Tris(trifluoromethyl)-4,5-difluoro-1,3-dioxolane-2-carboxylic acid；4,5-difluoro-2,4,5-tris(trifluoromethyl)-1,3-dioxolane-2-carboxylic acid
• CAS: 814916-39-7
• 化学式: C₇HF₁₁O₄
• 分子量: 358.065
• InChiKey: SITFKNCPEOZOBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  (perfluoro-2,4,5-trimethyl-1,3-dioxolane)-2-carboxylic acid 在 氢氧化钾 作用下， 反应 2.0h， 以78%的产率得到perfluoro-2-methylene-4,5-dimethyl-1,3-dioxolane
  参考文献：
  名称：

  Synthesis and Radical Polymerization of Perfluoro-2-methylene-1,3-dioxolanes

  摘要：

  A new efficient synthetic route was developed for perfluorinated 2-methylene-1,3-dioxolane monomers via a direct fluorination of the hydrocarbon precursors prepared from methyl pyruvate and diols. Perfluoro-2-methylene-4,5-dimethyl-1,3-dioxolane (PMDD) and perfluoro-3-methylene-2,4-dioxabicyclo[4.3.0]nonane (PMDN) were thus synthesized via this new method, among which PMDN is first reported. The radical polymerizations of those monomers were performed under various conditions. The kinetic results indicated that polymerization rate of PMDD is higher than that of PMDN. Oxygen did not affect the polymerization yield but strongly affected the polymer structure. The polymerization in the presence of oxygen produced a polymer containing unstable units. Hydrogen-containing solvents result in a lower molecular weight polymer. 2,2'-Azobis(isobutyronitrile) cannot initiate the polymerization in a perfluoro solvent or in bulk. Also, photopolymerizations of those monomers were performed in the presence of carbon tetrabromide or carbon tetrachloride, and the mechanism is discussed. The polymer of PMDD has a glass transition temperature at 155 degrees C, and the polymer of PMDN has a glass transition temperature at 161 degrees C. These polymers with high glass transition temperature, low refractive index, low material dispersion, and extraordinary optical transmission from the deep ultraviolet to near-infrared regions may be used as optical fibers, pellicles, or antireflective coating materials.

  DOI：

  10.1021/ma050753b
• 作为产物：
  描述：

  methyl 2,4,5-trimethyl-1,3-dioxolane-2-carboxylate 在 fluorine 作用下， 反应 20.0h， 以90%的产率得到(perfluoro-2,4,5-trimethyl-1,3-dioxolane)-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and Radical Polymerization of Perfluoro-2-methylene-1,3-dioxolanes

  摘要：

  A new efficient synthetic route was developed for perfluorinated 2-methylene-1,3-dioxolane monomers via a direct fluorination of the hydrocarbon precursors prepared from methyl pyruvate and diols. Perfluoro-2-methylene-4,5-dimethyl-1,3-dioxolane (PMDD) and perfluoro-3-methylene-2,4-dioxabicyclo[4.3.0]nonane (PMDN) were thus synthesized via this new method, among which PMDN is first reported. The radical polymerizations of those monomers were performed under various conditions. The kinetic results indicated that polymerization rate of PMDD is higher than that of PMDN. Oxygen did not affect the polymerization yield but strongly affected the polymer structure. The polymerization in the presence of oxygen produced a polymer containing unstable units. Hydrogen-containing solvents result in a lower molecular weight polymer. 2,2'-Azobis(isobutyronitrile) cannot initiate the polymerization in a perfluoro solvent or in bulk. Also, photopolymerizations of those monomers were performed in the presence of carbon tetrabromide or carbon tetrachloride, and the mechanism is discussed. The polymer of PMDD has a glass transition temperature at 155 degrees C, and the polymer of PMDN has a glass transition temperature at 161 degrees C. These polymers with high glass transition temperature, low refractive index, low material dispersion, and extraordinary optical transmission from the deep ultraviolet to near-infrared regions may be used as optical fibers, pellicles, or antireflective coating materials.

  DOI：

  10.1021/ma050753b

文献信息

• Multidimensional NMR characterization of perfluorinated monomer and its precursors
  作者：Bo Zhang、Linlin Li、František Mikeš、Yasuhiro Koike、Yoshiyuki Okamoto、Peter L. Rinaldi

  DOI：10.1016/j.jfluchem.2012.12.008

  日期：2013.3

  as their hydrocarbon precursor (methyl 2,4,5-trimethyl-1,3-dioxolane-2-carboxylate), were prepared and studied by 1D- and advanced 2D NMR techniques. For both perfluorinated compounds, the structures of their possible isomers were proven by 2D NMR spectroscopy. Due to the large 19F spectral window, this study used selective versions of the correlation spectroscopy (COSY) and nuclear Overhauser effect

  全氟化单体（全氟-2-亚甲基-4,5-二甲基-1,3-二氧戊环），它的前体（全氟-2,4,5-三甲基-1,3-二氧戊环-2-羧酸），以及他们的烃前体（甲基2,4,5-三甲基-1,3-二氧戊环-2-羧酸酯），制备并通过1D-和先进的2D NMR技术分析。对于这两种全氟化化合物，其可能的异构体的结构通过2D NMR光谱证实。由于大19 ˚F光谱窗口，本研究中使用的相关光谱（COZY）和核Overhauser效应光谱（NOESY）实验的选择性版本，以提供更好的分辨率和灵敏度。此外，梯度异核单量子相干谱的新变体（gHSQC）序列是成功的，用于观察两键19˚F 13 Ç相关性。与梯度异核多键相关光谱法（gHMBC）光谱相比，2 Ĵ FC gHSQC频谱被大大简化由于缺乏引起的多量子相干性分裂的。定量1 H或19 ˚F1D NMR被用于证实共振分配和计算的异构体的比率。全氟化的化合物的构型的组合物和它
• [EN] METHOD FOR PRODUCING FLUORINATED 1,3-DIOXOLANE COMPOUNDS, FLUORINATED 1,3-DIOXOLANE COMPOUNDS, FLUORINATED POLYMERS OF THE FLUORINATED 1,3-DIOXOLANE COMPOUNDS, AND OPTICAL OR ELECTRICAL MATERIALS USING THE POLYMERS<br/>[FR] PROCEDE POUR COMPOSES FLUORES, COMPOSES FLUORES PRODUITS SUIVANT CE PROCEDE, POLYMERES FLUORES DES COMPOSES FLUORES, ET MATERIAUX OPTIQUES OU ELECTRIQUES UTILISANT CES POLYMERES
  申请人：JAPAN SCIENCE & TECH AGENCY

  公开号：WO2005021526A3

  公开（公告）日：2005-06-30
• Fluorinated 1,3-Dioxolane Compounds, Fluorinated Polymers of the Compounds, and Optical or Electrical Materials Comprising the Polymers
  申请人：Okamoto Yoshiyuki

  公开号：US20100056752A1

  公开（公告）日：2010-03-04

  A production method of fluorinated compounds, for producing a compound represented by formula (3) in a fluorine-based solution in a flow of fluorine gas after reaction of at least one type of compounds represented by formula (1) and at least one type of compounds represented by formula (2). Similarly, fluorinated compounds represented by formula (4) prepared by the fluorination of compounds obtained by the reaction of formula (1) and formula (2)′. The fluorinated polymers obtained by the polymerizations of formula (3) and (4) compounds are useful as an optical or electrical materials. wherein R 1 , R 2 , R 3 , R 4 , R ff 1 , R ff 2 , R ff 3 , R ff 4 , X, Y, Z, and n are defined in the specification respectively.
• US8168808B2
  申请人：——

  公开号：US8168808B2

  公开（公告）日：2012-05-01
• Synthesis and Radical Polymerization of Perfluoro-2-methylene-1,3-dioxolanes
  作者：Weihong Liu、Yasuhiro Koike、Yoshi Okamoto

  DOI：10.1021/ma050753b

  日期：2005.11.1

  A new efficient synthetic route was developed for perfluorinated 2-methylene-1,3-dioxolane monomers via a direct fluorination of the hydrocarbon precursors prepared from methyl pyruvate and diols. Perfluoro-2-methylene-4,5-dimethyl-1,3-dioxolane (PMDD) and perfluoro-3-methylene-2,4-dioxabicyclo[4.3.0]nonane (PMDN) were thus synthesized via this new method, among which PMDN is first reported. The radical polymerizations of those monomers were performed under various conditions. The kinetic results indicated that polymerization rate of PMDD is higher than that of PMDN. Oxygen did not affect the polymerization yield but strongly affected the polymer structure. The polymerization in the presence of oxygen produced a polymer containing unstable units. Hydrogen-containing solvents result in a lower molecular weight polymer. 2,2'-Azobis(isobutyronitrile) cannot initiate the polymerization in a perfluoro solvent or in bulk. Also, photopolymerizations of those monomers were performed in the presence of carbon tetrabromide or carbon tetrachloride, and the mechanism is discussed. The polymer of PMDD has a glass transition temperature at 155 degrees C, and the polymer of PMDN has a glass transition temperature at 161 degrees C. These polymers with high glass transition temperature, low refractive index, low material dispersion, and extraordinary optical transmission from the deep ultraviolet to near-infrared regions may be used as optical fibers, pellicles, or antireflective coating materials.