methyl 3-methyl-2,4-dioxabicyclo[4.3.0]nonane-3-carboxylate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-methyl-2,4-dioxabicyclo[4.3.0]nonane-3-carboxylate
• 英文别名: 2-methyl-2-methoxycarbonyl-4,5-cyclotetramethylene-1,3-dioxolane；Methyl 2-methyl-3a,4,5,6,7,7a-hexahydro-1,3-benzodioxole-2-carboxylate
• 化学式: C₁₀H₁₆O₄
• 分子量: 200.235
• InChiKey: GJLWHCQNOJLYRM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 3-methyl-2,4-dioxabicyclo[4.3.0]nonane-3-carboxylate 在 fluorine 作用下， 反应 26.0h， 以94%的产率得到(perfluoro-3-methyl-2,4-dioxabicyclo[4.3.0]nonane)-3-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
• 作为产物：
  描述：

  丙酮酸甲酯 、 1,2-环己二醇 在 cation-exchange resin (H form) 作用下， 以 苯 为溶剂， 以58%的产率得到methyl 3-methyl-2,4-dioxabicyclo[4.3.0]nonane-3-carboxylate
  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

• Fluorinated compounds, fluorinated polymers of the fluorinated compounds, and optical or electrical materials using the polymers
  申请人：Japan Science and Technology Agency

  公开号：EP2107056A1

  公开（公告）日：2009-10-07

  A fluorinated compound represented by the following formula (4): wherein, in formula (4), Rff1 and Rff2 each independently represent a fluorine atom or a perfluoroalkyl group having 1 to 7 carbon atoms, and n represents an integer from 1 to 4.

  下式(4)所代表的含氟化合物： 其中，在式 (4) 中，Rff1 和 Rff2 各自独立地代表一个氟原子或一个具有 1 至 7 个碳原子的全氟烷基，n 代表 1 至 4 的整数。
• [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
• 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
  申请人：Japan Science and Technology Agency

  公开号：EP1658278A2

  公开（公告）日：2006-05-24
• 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
  申请人：Okamoto Yoshiyuki

  公开号：US20070043187A1

  公开（公告）日：2007-02-22

  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.
• 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.