(E)-2,3-二氟丁-2-烯二酸 | 2714-32-1

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: (E)-2,3-二氟丁-2-烯二酸
• 中文别名: 2,3-二氟富马酸
• 英文名称: difluorofumaric acid
• 英文别名: Difluorfumarsaeure；Difluor-fumarsaeure；Difluorofumarsaeure；2,3-Difluorofumaric acid；(E)-2,3-difluorobut-2-enedioic acid
• CAS: 2714-32-1
• 化学式: C₄H₂F₂O₄
• 分子量: 152.054
• InChiKey: JUVWKFKXIVLAHQ-OWOJBTEDSA-N

物化性质

• 熔点：
  268-270 °C(Solv: water (7732-18-5))
• 沸点：
  291.9±40.0 °C(Predicted)
• 密度：
  1.729±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-2,3-二氟丁-2-烯二酸 在 五氯化磷 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以49%的产率得到difluorofumaric acid dichloride
  参考文献：
  名称：

  Lentz, Dieter; Preugschat, Dagmar, Angewandte Chemie, 1990, vol. 102, # 3, p. 308 - 310

  摘要：

  DOI：
• 作为产物：
  描述：

  trans,trans-2,3,4,5-Tetrafluoro-2,4-hexadienedioic Acid 在 过氧乙酸 作用下， 生成 (E)-2,3-二氟丁-2-烯二酸
  参考文献：
  名称：

  Kobrina,L.S. et al., Journal of Organic Chemistry USSR (English Translation), 1972, vol. 8, p. 2209 - 2211

  摘要：

  DOI：

文献信息

• Interaction of pentafluorophenol with lead tetraacetate in acids
  作者：V.N. Kovtonyuk、L.S. Kobrina、G.G. Yakobson

  DOI：10.1016/s0022-1139(00)85195-7

  日期：1985.5

  The ability of polyfluorinated hydroxyaromatic compounds to be oxidised by radical and ionic mechanisms is discussed. Oxidation of pentafluorophenol by lead tetraacetate in hydrogen fluoride and trifluoroacetic acid gave the products of a reaction proceeding by an ionic mechanism-hexafluorocyclo- hexa-2,5-dienone and trifluoroacetoxydienones respectively.

  讨论了多氟羟基芳香化合物被自由基和离子机理氧化的能力。用四乙酸铅在氟化氢和三氟乙酸中氧化五氟苯酚，得到的反应产物分别通过离子机理进行反应，分别是六氟环-六-2,5-二烯酮和三氟乙酰氧基二壬烯。
• cis-1,2-dicyan-1,2-difluor-äthylen
  作者：K. Wallenfels、F. Witzler

  DOI：10.1016/0040-4020(67)85089-0

  日期：1967.1

  Vapour phase fluorination of dichlorofumaric acid dinitrile by a mixture of fluorides of alkaline/alkaline earth metals yields the dinitriles of difluoromaleic acid, chlorofluoromaleic acid and chlorofluorofumaric acid. Some reaction products of difluoromaleic acid dinitrile are described.

  用碱金属/碱土金属的氟化物的混合物汽相氟化二氯富马酸二腈，得到二氟马来酸，氯氟马来酸和氯氟富马酸的二腈。描述了二氟马来酸二腈的一些反应产物。
• Molecular Structure of 3,4-Difluorofuran-2,5-dione (Difluoromaleic Anhydride) As Determined by Electron Diffraction and Microwave Spectroscopy in the Gas Phase and by Theoretical Computations
  作者：Basil T. Abdo、Halima Amer、R. Eric Banks、Paul T. Brain、A. Peter Cox、Oliver J. Dunning、Vincent Murtagh、David W. H. Rankin、Heather E. Robertson、Bruce A. Smart

  DOI：10.1021/jp984554o

  日期：1999.3.25

  The structure of 3,4-difluorofuran-2,5-dione has been determined experimentally in the gas phase by microwave spectroscopy using rotation constants derived from five isotopomers and by a combined analysis of electron-diffraction and microwave data. The geometry is planar with C-2v symmetry. Structural parameters [distances (r(alpha)degrees)/pm, angles angle(alpha)/deg, (1 sigma errors)] for the combined analysis are: r(C=O) = 119.0(1); r(C-F) = 130.9(2); r-(C=C) = 133.2(3), r(O-C) = 139.3(1); r(C-C) = 148.5(2); angle C-C=C = 108.3(1); angle C=C-F = 129.9(1); angle C-C=O = 129.3(1); angle C-O-C = 108.9(1); angle O-C-C = 107.2(1). These values are in excellent agreement with those obtained in an ab initio study of the molecular geometry at the MP2/6-311+G*(2df) level of theory. The dipole moment of difluoromaleic anhydride has been determined experimentally by Stark-effect measurements to be 1.867(3) D.
• Mono- and Difluorobutenedioic Acids
  作者：Maynard S. Raasch、Ralph E. Miegel、John E. Castle

  DOI：10.1021/ja01520a023

  日期：1959.6
• Hydrogen-Bond Symmetry in Difluoromaleate Monoanion
  作者：Charles L. Perrin、Phaneendrasai Karri、Curtis Moore、Arnold L. Rheingold

  DOI：10.1021/ja2117848

  日期：2012.5.9

  The symmetry of the hydrogen bond in hydrogen difluoromaleate monoanion is probed by X-ray crystallography and by the NMR method of isotopic perturbation in water, in two aprotic organic solvents, and in an isotropic liquid crystal. The X-ray crystal structure of potassium hydrogen difluoromaleate shows a remarkably short O-O distance of 2.41 angstrom and equal O-H distances of 1.206 angstrom, consistent with a strong and symmetric hydrogen bond. Incorporation of O-18 into one carboxyl group allows investigation of the symmetry of the H-bond in solution by the method of isotopic perturbation. The F-19 NMR spectra of the mono-O-18-substituted monoanion in water, CD2Cl2, and CD3CN show an AB spin system, corresponding to fluorines in different environments. The difference is attributed to the perturbation of the acidity of a carboxylic acid by O-18, not to the mere presence of the O-18, because the mono-O-18 dianion shows equivalent fluorines. Therefore, it is concluded that the monoanion exists as an equilibrating pair of interconverting tautomers and not as a single symmetric structure not only in water but also in organic solvents. However, in the isotropic liquid crystal phase of 4-cyanophenyl 4-heptylbenzoate, tetrabutylammonium hydrogen difluoromaleate-O-18 shows equivalent fluorines, consistent with a single symmetric structure. These results support earlier studies, which suggested that the symmetry of hydrogen bonds can be determined by the local environment.