2,2,3-三氟丁二酸 | 664-66-4

• 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: 2,2,3-三氟丁二酸
• 英文名称: 2,2,3-trifluorosuccinic acid
• 英文别名: trifluorosuccinic acid；trifluoro-succinic acid；Trifluor-bernsteinsaeure；Trifluorbernsteinsaeure；2,2,3-Trifluoro-succinic acid；2,2,3-trifluorobutanedioic acid
• CAS: 664-66-4；28812-58-0
• 化学式: C₄H₃F₃O₄
• 分子量: 172.061
• InChiKey: ONVXOMZCAAXUJR-UHFFFAOYSA-N

物化性质

• 沸点：
  228.6±35.0 °C(Predicted)
• 密度：
  1.710±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  7

安全信息

• 海关编码：
  2917190090

反应信息

• 作为反应物：
  描述：

  2,2,3-三氟丁二酸 在 氘氧化钠 作用下， 以 重水 为溶剂， 生成 difluoromaleic acid
  参考文献：
  名称：

  从氟化琥珀酸中消除氟化氢。（II）氟，2,2-二氟，内消旋和DL-2,3-二氟和三氟琥珀酸的脱氟化氢动力学

  摘要：

  从氟代琥珀酸中除去氟化氢，得到富马酸，由2，2-二氟琥珀酸，内消旋和DL-2，3-二氟琥珀酸的氟富马酸，和三氟琥珀酸的脱氢氟化得到二氟马来酸。给出了基于1 H NMR测量的60°，75°和90°温度的动力学数据。所有的脱氟化氢反应都遵循二级动力学。发现上述酸的脱氟化氢的活化能分别为：19.3kcal，17.3kcal，18.8kcal，17.9kcal和18.3kcal。由于两种非对映异构体2,3-二氟琥珀酸均将氟富马酸作为脱氟化氢的唯一产物，因此其中一个（DL）进行了反式消除，而另一个（meso）必须进行了顺式消除。

  DOI：

  10.1016/s0022-1139(00)81275-0
• 作为产物：
  描述：

  一氯三氟代丁二酸 在 锌 锌 、 1,4-二氧六环 、 水 、 硫酸 、 乙醚 、 magnesium sulfate 作用下， 以 1,4-二氧六环 为溶剂， 反应 10.0h， 以to yield 8.3 g (32%) of the product as a crystalline solid的产率得到2,2,3-三氟丁二酸
  参考文献：
  名称：

  Dihydropyridazinones, pyridazinones and related compounds as fungicides

  摘要：

  本发明涉及取代的二氢吡啶嗪酮，吡啶嗪酮和相关化合物，其化学式为##STR1## 其中A、Q、D和R1的定义如内部所述，包含这些化合物的组合物以及控制农业和哺乳动物真菌病的方法。

  公开号：

  US05728694A1

文献信息

• The formation of halogenated succinates by liquid-phase direct fluorination with elemental fluorine
  作者：Robert G. Syvret、Daniel L. Vassilaros、David M. Parees、Guido P. Pez

  DOI：10.1016/0022-1139(93)02975-k

  日期：1994.6

  Direct fluorination of maleic anhydride with elemental fluorine has been investigated in different solvents at low temperatures. It was discovered that the net conversion of maleic anhydride, as well as the overall yield and composition of the halogenated products, depend strongly on the experimental conditions employed. Fluorinations conducted in fluorotrichloromethane, chloroform or mixtures thereof

  已经在低温下在不同溶剂中研究了马来酸酐与元素氟的直接氟化。已经发现，马来酸酐的净转化率以及卤代产物的总产率和组成在很大程度上取决于所采用的实验条件。在氟化钠存在下，在氟代三氯甲烷，氯仿或它们的混合物中进行的氟化反应可产生高产率的卤代琥珀酸衍生物：主要产物为2，3-二卤代琥珀酸。在0°C和-25°C下进行的实验之间以及在纯CHCl 3和CFCl 3 / CHCl 3中进行的实验之间，产物分布差异很大混合物。提供了有关卤素添加的立体选择性的实验细节和一些评论。
• 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.