8-fluoro-1-isopropoxy-5-methoxy-2-naphthaldehyde | 158095-43-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 8-fluoro-1-isopropoxy-5-methoxy-2-naphthaldehyde
• 英文别名: 8-Fluoro-5-methoxy-1-propan-2-yloxynaphthalene-2-carbaldehyde
• CAS: 158095-43-3
• 化学式: C₁₅H₁₅FO₃
• 分子量: 262.281
• InChiKey: LJILVMWROMLJLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-乙基4-(叔-丁基)2-(二乙基膦酰)琥珀酸盐 、 8-fluoro-1-isopropoxy-5-methoxy-2-naphthaldehyde 在 三氟乙酸 、 lithium diisopropyl amide 作用下， 生成 3-ethoxycarbonyl-4-(8-fluoro-5-methoxy-1-propan-2-yloxynaphthalen-2-yl)but-3-enoic acid
  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 在 palladium on activated charcoal 三氯化铝 、 高氯酸 、 氢气 、 sodium hydride 、 potassium carbonate 、 硫酸二甲酯 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 溶剂黄146 、 乙腈 、 paraffin 为溶剂， 5.0~90.0 ℃ 、413.69 kPa 条件下， 反应 50.08h， 生成 8-fluoro-1-isopropoxy-5-methoxy-2-naphthaldehyde
  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

• Owton W. Martin, J. Chem. Soc. Perkin Trans. 1, (1994) N 15, S 2131-2135
  作者：Owton W. Martin

  DOI：——

  日期：——
• 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.