Ethyl 4-(5-fluoro-2-methoxyphenyl)-4-oxobutanoate | 951889-81-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Ethyl 4-(5-fluoro-2-methoxyphenyl)-4-oxobutanoate
• CAS: 951889-81-9
• 化学式: C₁₃H₁₅FO₄
• mdl: MFCD09801991
• 分子量: 254.258
• InChiKey: QKOGRSSZACZENF-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：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.384
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Ethyl 4-(5-fluoro-2-methoxyphenyl)-4-oxobutanoate 在 palladium on activated charcoal 高氯酸 、 氢气 作用下， 以 溶剂黄146 为溶剂， 90.0 ℃ 、413.69 kPa 条件下， 反应 0.75h， 生成 8-fluoro-5-methoxy-1,2,3,4-tetrahydronaphthalen-1-one
  参考文献：
  名称：

  Synthesis of 8-fluororhein

  摘要：

  8-Fluoro-5-methoxy-1-tetralone has been formylated. aromatised and alkylated to give 8-fluoro-1-isopropoxy-5-methoxy-2-naphthaldehyde 11. Condensation of this with a phosphonosuccinate gave, after deprotection, the 4-naphthylbutenoic acid which was cyclised and methylated to give the ethyl 9-fluoro-10-isopropoxy-4,6-dimethoxy-2-carboxylate 12. Removal of the isopropyl group, dichromate oxidation and deprotection gave 8-fluorohein 3, an analogue of the osteoarthritis drug rhein.

  DOI：

  10.1039/p19940002131
• 作为产物：
  描述：

  对氟苯甲醚 、 丁二酸单乙酯酰氯 在 三氯化铝 、 potassium carbonate 、 硫酸二甲酯 作用下， 生成 Ethyl 4-(5-fluoro-2-methoxyphenyl)-4-oxobutanoate
  参考文献：
  名称：

  Synthesis of 8-fluororhein

  摘要：

  8-Fluoro-5-methoxy-1-tetralone has been formylated. aromatised and alkylated to give 8-fluoro-1-isopropoxy-5-methoxy-2-naphthaldehyde 11. Condensation of this with a phosphonosuccinate gave, after deprotection, the 4-naphthylbutenoic acid which was cyclised and methylated to give the ethyl 9-fluoro-10-isopropoxy-4,6-dimethoxy-2-carboxylate 12. Removal of the isopropyl group, dichromate oxidation and deprotection gave 8-fluorohein 3, an analogue of the osteoarthritis drug rhein.

  DOI：

  10.1039/p19940002131

文献信息

• Synthesis of 8-fluororhein
  作者：W. Martin Owton

  DOI：10.1039/p19940002131

  日期：——

  8-Fluoro-5-methoxy-1-tetralone has been formylated. aromatised and alkylated to give 8-fluoro-1-isopropoxy-5-methoxy-2-naphthaldehyde 11. Condensation of this with a phosphonosuccinate gave, after deprotection, the 4-naphthylbutenoic acid which was cyclised and methylated to give the ethyl 9-fluoro-10-isopropoxy-4,6-dimethoxy-2-carboxylate 12. Removal of the isopropyl group, dichromate oxidation and deprotection gave 8-fluorohein 3, an analogue of the osteoarthritis drug rhein.