ethyl 2-(2-hydroxy-3,4,5,6-tetrafluorobenzoyl)-3-phenyl-3-(cyclohexylamino)acrylate | 1443627-71-1

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: ethyl 2-(2-hydroxy-3,4,5,6-tetrafluorobenzoyl)-3-phenyl-3-(cyclohexylamino)acrylate
• 英文别名: ethyl 3-(cyclohexylamino)-3-phenyl-2-(2,3,4,5-tetrafluoro-6-hydroxybenzoyl)prop-2-enoate
• CAS: 1443627-71-1
• 化学式: C₂₄H₂₃F₄NO₄
• 分子量: 465.445
• InChiKey: HCDCPIKFTWLCDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.03
• 重原子数：
  33.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  75.63
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-(2-hydroxy-3,4,5,6-tetrafluorobenzoyl)-3-phenyl-3-(cyclohexylamino)acrylate 反应 1.0h， 生成 5,6,7,8-tetrafluoro-3-[(cyclohexylamino)-(phenyl)methylene]-2H-chromene-2,4(3H)-dione
  参考文献：
  名称：

  Features of reactions of polyfluorinated ethyl 4-oxo-2-pnenyl-4H-chromene-3-carboxylates with N-nucleophiles

  摘要：

  Ethyl 5,6,7,8-tetrafluoro-4-oxo-2-phenyl-4H-chromene-3-carboxylate in reactions with primary amines is characterized by a chromone-coumarin rearrangement affording 3-[amino(phenyl)methylene]-6,7,8-trifluoro-2H-chromene-2,4(3H)-diones, and ethyl 4-oxo-2-phenyl-5,6,7,8-tetrafluoro-4H-chromene-3-carboxylate characteristically adds the amine at the C-2 site of the flavone furnishing 3-amino-3-phenyl-2-(2,3,4,5-tetrafluoro-6-hydroxybenzoyl)acrylates which depending on the substituent at the amino group are capable of intramolecular cyclization into 3-[(alkylamino)(phenyl)methylene]-5,6,7,8-tetrafluoro-2H-chromene-2,4(3H)-dione or in the case of benzylamine substituent, into ethyl 1-benzyl-5-hydroxy-4-oxo-2-phenyl-6,7,8-trifluoro-1,4-dihydroquinoline-3-carboxylate. The main process in the reaction of tri- and tetrafluoroflavones with secondary amine (1-methylpiperazine) is the nucleophilic substitution at the C-7 of flavone. In the reaction with 1,2-phenylenediamine 3-[(2-aminophenyl)amino]-3-phenyl-2-(2,3,4,5-tetrafluoro-6-hydroxybenzoyl)acrylate was obtained from tetrafluoroflavone and 1H-benzimidazol-2-yl(3,4,5-trifluoro-2-hydroxyphenyl)methanone, from trifluoroflavone.

  DOI：

  10.1134/s1070428013050151
• 作为产物：
  描述：

  苯甲酰乙酸乙酯 在 四氯化碳 、 乙醇 、 碘 、 magnesium 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 30.0h， 生成 ethyl 2-(2-hydroxy-3,4,5,6-tetrafluorobenzoyl)-3-phenyl-3-(cyclohexylamino)acrylate 、 5,6,7,8-tetrafluoro-3-[(cyclohexylamino)-(phenyl)methylene]-2H-chromene-2,4(3H)-dione
  参考文献：
  名称：

  Features of reactions of polyfluorinated ethyl 4-oxo-2-pnenyl-4H-chromene-3-carboxylates with N-nucleophiles

  摘要：

  Ethyl 5,6,7,8-tetrafluoro-4-oxo-2-phenyl-4H-chromene-3-carboxylate in reactions with primary amines is characterized by a chromone-coumarin rearrangement affording 3-[amino(phenyl)methylene]-6,7,8-trifluoro-2H-chromene-2,4(3H)-diones, and ethyl 4-oxo-2-phenyl-5,6,7,8-tetrafluoro-4H-chromene-3-carboxylate characteristically adds the amine at the C-2 site of the flavone furnishing 3-amino-3-phenyl-2-(2,3,4,5-tetrafluoro-6-hydroxybenzoyl)acrylates which depending on the substituent at the amino group are capable of intramolecular cyclization into 3-[(alkylamino)(phenyl)methylene]-5,6,7,8-tetrafluoro-2H-chromene-2,4(3H)-dione or in the case of benzylamine substituent, into ethyl 1-benzyl-5-hydroxy-4-oxo-2-phenyl-6,7,8-trifluoro-1,4-dihydroquinoline-3-carboxylate. The main process in the reaction of tri- and tetrafluoroflavones with secondary amine (1-methylpiperazine) is the nucleophilic substitution at the C-7 of flavone. In the reaction with 1,2-phenylenediamine 3-[(2-aminophenyl)amino]-3-phenyl-2-(2,3,4,5-tetrafluoro-6-hydroxybenzoyl)acrylate was obtained from tetrafluoroflavone and 1H-benzimidazol-2-yl(3,4,5-trifluoro-2-hydroxyphenyl)methanone, from trifluoroflavone.

  DOI：

  10.1134/s1070428013050151