1-(2-carboxyphenyl)-4,4,4-trifluorobutane-1,3-dione

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-carboxyphenyl)-4,4,4-trifluorobutane-1,3-dione
• 英文别名: 4,4,4-Trifluoro-1-(2-carboxyphenyl)butane-1,3-dione；2-(4,4,4-trifluoro-3-oxobutanoyl)benzoic acid
• 化学式: C₁₁H₇F₃O₄
• 分子量: 260.169
• InChiKey: SDONTRYCUPTLJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  71.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(2-carboxyphenyl)-4,4,4-trifluorobutane-1,3-dione 生成 (3E)-3-(3,3,3-trifluoro-2-oxopropylidene)-2-benzofuran-1-one 、 3-[(Z)-2-Oxo-3,3,3-trifluoropropylidene]isobenzofuran-1(3H)-one
  参考文献：
  名称：

  摘要：

  3-Polyfluoroacylmethylenephthalides (R-F = CF3, CF2CF2H, C2F5) can be synthesized conveniently by cyclodehydration of 1-(2-carboxyphenyl)-3-polyfluoroalkylpropane-1,3-diones, obtained from o-acetylbenzoic acid and polyfluorinated esters, as a separable mixture of Z- and E-isomers. In solution, the Z- and E-isomers of 3-polyfluoroacylmethylenephthalides are interconvertable. For CD3CN and (CD3)(2)SO solutions of 1-(2-carboxyphenyl)-3-polyfluoroalkylpropane- 1,3-diones a ring-chain tautomerism is observed. The structures of the new compounds have been determined by heteronuclear nuclear magnetic resonance (NMR) spectroscopy and nuclear Overhauser effect (NOE) experiments.

  DOI：

  10.1071/ch01086
• 作为产物：
  描述：

  2-乙酰苯甲酸 、 三氟乙酸乙酯 在 sodium methylate 作用下， 以 四氢呋喃 为溶剂， 以68%的产率得到1-(2-carboxyphenyl)-4,4,4-trifluorobutane-1,3-dione
  参考文献：
  名称：

  摘要：

  3-Polyfluoroacylmethylenephthalides (R-F = CF3, CF2CF2H, C2F5) can be synthesized conveniently by cyclodehydration of 1-(2-carboxyphenyl)-3-polyfluoroalkylpropane-1,3-diones, obtained from o-acetylbenzoic acid and polyfluorinated esters, as a separable mixture of Z- and E-isomers. In solution, the Z- and E-isomers of 3-polyfluoroacylmethylenephthalides are interconvertable. For CD3CN and (CD3)(2)SO solutions of 1-(2-carboxyphenyl)-3-polyfluoroalkylpropane- 1,3-diones a ring-chain tautomerism is observed. The structures of the new compounds have been determined by heteronuclear nuclear magnetic resonance (NMR) spectroscopy and nuclear Overhauser effect (NOE) experiments.

  DOI：

  10.1071/ch01086

文献信息

• ——
  作者：Dmitri V. Sevenard、Vyacheslav Ya. Sosnovskikh、Grzegorz Schroeder、Gerd-Volker Röschenthaler

  DOI：10.1071/ch01086

  日期：——

  3-Polyfluoroacylmethylenephthalides (R-F = CF3, CF2CF2H, C2F5) can be synthesized conveniently by cyclodehydration of 1-(2-carboxyphenyl)-3-polyfluoroalkylpropane-1,3-diones, obtained from o-acetylbenzoic acid and polyfluorinated esters, as a separable mixture of Z- and E-isomers. In solution, the Z- and E-isomers of 3-polyfluoroacylmethylenephthalides are interconvertable. For CD3CN and (CD3)(2)SO solutions of 1-(2-carboxyphenyl)-3-polyfluoroalkylpropane- 1,3-diones a ring-chain tautomerism is observed. The structures of the new compounds have been determined by heteronuclear nuclear magnetic resonance (NMR) spectroscopy and nuclear Overhauser effect (NOE) experiments.