4,5,8-trimethoxy-2-methylanthracen-10-ol

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 4,5,8-trimethoxy-2-methylanthracen-10-ol
• 英文别名: 1,5,8-Trimethoxy-3-methylanthracen-9-ol
• 化学式: C₁₈H₁₈O₄
• 分子量: 298.339
• InChiKey: FGBHWNXYSSTBDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,5,8-trimethoxy-2-methylanthracen-10-ol 在 potassium dichromate 作用下， 以 溶剂黄146 为溶剂， 反应 0.5h， 以93%的产率得到helminthosporin trimethyl ether
  参考文献：
  名称：

  Synthesis of 4,5,8-trimethoxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid, an analogue of rhein with improved systemic exposure in the guinea pig

  摘要：

  N,N-Diethyl(2-methoxy-4-methyl)benzamide 4 has been lithiated and treated with 2,5-dimethoxybenzaldehyde to give 3-(2',5'-dimethoxyphenyl)-7-methoxy-5-methylisobenzofuran-1(3H)-one 5. Reduction and cyclisation gives 4,5,8-trimethoxy-2-methylanthracen-10-ol 7 which is oxidised to give 4,5,8-trimethoxy-2-methylanthraquinone 8. Demethylation gives the natural product helminthosporin 9, oxidation gives 4,5,8-trimethoxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid an analogue of the osteoarthritis drug rhein, Alternatively, dimethylrhein methyl ester 12 may be iodinated and the iodine displaced with methoxide to provide a large-scale synthesis of 3. Plasma concentration data in the guinea pig were obtained for 3, diacetylrhein, dimethylrhein and 4,5-dimethyl-8-fluororhein after oral dosing.

  DOI：

  10.1039/p19950000931
• 作为产物：
  描述：

  2-(2',5'-dimethoxybenzyl)-6-methoxy-4-methylbenzoic acid 在 草酰氯 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 以76%的产率得到4,5,8-trimethoxy-2-methylanthracen-10-ol
  参考文献：
  名称：

  Synthesis of 4,5,8-trimethoxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid, an analogue of rhein with improved systemic exposure in the guinea pig

  摘要：

  N,N-Diethyl(2-methoxy-4-methyl)benzamide 4 has been lithiated and treated with 2,5-dimethoxybenzaldehyde to give 3-(2',5'-dimethoxyphenyl)-7-methoxy-5-methylisobenzofuran-1(3H)-one 5. Reduction and cyclisation gives 4,5,8-trimethoxy-2-methylanthracen-10-ol 7 which is oxidised to give 4,5,8-trimethoxy-2-methylanthraquinone 8. Demethylation gives the natural product helminthosporin 9, oxidation gives 4,5,8-trimethoxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid an analogue of the osteoarthritis drug rhein, Alternatively, dimethylrhein methyl ester 12 may be iodinated and the iodine displaced with methoxide to provide a large-scale synthesis of 3. Plasma concentration data in the guinea pig were obtained for 3, diacetylrhein, dimethylrhein and 4,5-dimethyl-8-fluororhein after oral dosing.

  DOI：

  10.1039/p19950000931

文献信息

• Owton W. Martin, Brunavs Michael, Miles Martin V., Dobson David R., Stegg+, J. Chem. Soc. Perkin Trans, (1995) N 7, S 931-934
  作者：Owton W. Martin, Brunavs Michael, Miles Martin V., Dobson David R., Stegg+

  DOI：——

  日期：——
• Synthesis of 4,5,8-trimethoxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid, an analogue of rhein with improved systemic exposure in the guinea pig
  作者：W. Martin Owton、Michael Brunavs、Martin V. Miles、David R. Dobson、David J. Steggles

  DOI：10.1039/p19950000931

  日期：——

  N,N-Diethyl(2-methoxy-4-methyl)benzamide 4 has been lithiated and treated with 2,5-dimethoxybenzaldehyde to give 3-(2',5'-dimethoxyphenyl)-7-methoxy-5-methylisobenzofuran-1(3H)-one 5. Reduction and cyclisation gives 4,5,8-trimethoxy-2-methylanthracen-10-ol 7 which is oxidised to give 4,5,8-trimethoxy-2-methylanthraquinone 8. Demethylation gives the natural product helminthosporin 9, oxidation gives 4,5,8-trimethoxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid an analogue of the osteoarthritis drug rhein, Alternatively, dimethylrhein methyl ester 12 may be iodinated and the iodine displaced with methoxide to provide a large-scale synthesis of 3. Plasma concentration data in the guinea pig were obtained for 3, diacetylrhein, dimethylrhein and 4,5-dimethyl-8-fluororhein after oral dosing.