ethyl 8-fluoro-9,10-dihydro-4,5-dimethoxy-9-oxoanthracene-2-carboxylate | 158095-45-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: ethyl 8-fluoro-9,10-dihydro-4,5-dimethoxy-9-oxoanthracene-2-carboxylate
• 英文别名: ethyl 8-fluoro-4,5-dimethoxy-9-oxo-10H-anthracene-2-carboxylate
• CAS: 158095-45-5
• 化学式: C₁₉H₁₇FO₅
• 分子量: 344.339
• InChiKey: GCGHMRBZEINCDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 8-fluoro-9,10-dihydro-4,5-dimethoxy-9-oxoanthracene-2-carboxylate 在 sodium dichromate 作用下， 以 溶剂黄146 为溶剂， 反应 0.33h， 以96%的产率得到ethyl 8-fluoro-9,10-dihydro-4,5-dimethoxy-9,10-dioxoanthracene-2-carboxylate
  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：

  ethyl 9-fluoro-9-isopropoxy-4,6-dimethoxyanthracene-2-carboxylate 在 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以93%的产率得到ethyl 8-fluoro-9,10-dihydro-4,5-dimethoxy-9-oxoanthracene-2-carboxylate
  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.