3-(Z)-(2,2,3,3-tetrafluoro-propionyl)methylenephthalide | 420109-44-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: 3-(Z)-(2,2,3,3-tetrafluoro-propionyl)methylenephthalide
• 英文别名: (3Z)-3-(3,3,4,4-tetrafluoro-2-oxobutylidene)-2-benzofuran-1-one
• CAS: 420109-44-0
• 化学式: C₁₂H₆F₄O₃
• 分子量: 274.171
• InChiKey: HTPASEZACPJJTP-YVMONPNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-(Z)-(2,2,3,3-tetrafluoro-propionyl)methylenephthalide 以 氘代氯仿 、 水 为溶剂， 生成 3-(E)-(2,2,3,3-tetrafluoro-propionyl)methylenephthalide
  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 在 sodium methylate 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.0h， 生成 3-(Z)-(2,2,3,3-tetrafluoro-propionyl)methylenephthalide
  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.