5-氟-7-羟基甲基12-甲基苯并蒽乙酸酯 | 67639-46-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 中文名称: 5-氟-7-羟基甲基12-甲基苯并蒽乙酸酯
• 英文名称: (5-Fluoro-12-methylbenzo[a]anthracen-7-yl)methyl acetate
• CAS: 67639-46-7
• 化学式: C₂₂H₁₇FO₂
• 分子量: 332.374
• InChiKey: BWBNQGMPRXNAEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-氟-7-羟基甲基12-甲基苯并蒽乙酸酯 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 5-氟-7-羟基甲基-12-甲基苯并蒽
  参考文献：
  名称：

  Synthesis and carcinogenic activity of 5-fluoro-7-(oxygenated methyl)-12-methylbenz[a]anthracenes

  摘要：

  Treatment of 7,12-benz[a]anthraquinone (2) with methylmagnesium iodide or methyllithium yields mixtures of cis- and trans-7,12-dihydro-7,12-dihydroxy-7,12-dimethylbenz[a]anthracenes (3a,b), in which the ratio of cis to trans lies in the 3--4:1 region. Each isomer afforded high yields of 7-chloromethyl-12-methylbenz[a]anthracene (5) on treatment with hydrogen chloride in ethyl acetate. Similarly, 5-fluoro-7,12-benz[a]anthraquinone (8) afforded a mixture of cis- and trans-5-fluoro-7,12-dihydro-7,12-dihydroxy-7,12-dimethylbenz[a]anthracenes (9) which yielded 7-chloromethyl-5-fluoro-12-methylbenz[a]anthracene (10) on treatment with HCl. The chloromethyl compounds, 5 and 10, yielded 7-acetoxymethyl-12-methylbenz[a]anthracene (6) and 7-acetoxymethyl-5-fluoro-12-methylbenz[a]anthracene (11) on treatment with acetate ion. Hydrolysis of 6 and 11 yielded 7-hydroxymethyl-12-methylbenz[a]anthracene (7) and 5-fluoro-7-hydroxymethyl-12-methylbenz[a]anthracene (12), respectively. Since neither 11 nor 12 is appreciably carcinogenic, the carcinogenic metabolism of 7,12-dimethylbenz[a]anthracene (DMBA) probably does not involve attack at the 7-methyl group.

  DOI：

  10.1021/jm00208a013
• 作为产物：
  描述：

  (7S,12R)-5-fluoro-7,12-dimethylbenzo[a]anthracene-7,12-diol 在 盐酸 、 18-冠醚-6 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 生成 5-氟-7-羟基甲基12-甲基苯并蒽乙酸酯
  参考文献：
  名称：

  Synthesis and carcinogenic activity of 5-fluoro-7-(oxygenated methyl)-12-methylbenz[a]anthracenes

  摘要：

  Treatment of 7,12-benz[a]anthraquinone (2) with methylmagnesium iodide or methyllithium yields mixtures of cis- and trans-7,12-dihydro-7,12-dihydroxy-7,12-dimethylbenz[a]anthracenes (3a,b), in which the ratio of cis to trans lies in the 3--4:1 region. Each isomer afforded high yields of 7-chloromethyl-12-methylbenz[a]anthracene (5) on treatment with hydrogen chloride in ethyl acetate. Similarly, 5-fluoro-7,12-benz[a]anthraquinone (8) afforded a mixture of cis- and trans-5-fluoro-7,12-dihydro-7,12-dihydroxy-7,12-dimethylbenz[a]anthracenes (9) which yielded 7-chloromethyl-5-fluoro-12-methylbenz[a]anthracene (10) on treatment with HCl. The chloromethyl compounds, 5 and 10, yielded 7-acetoxymethyl-12-methylbenz[a]anthracene (6) and 7-acetoxymethyl-5-fluoro-12-methylbenz[a]anthracene (11) on treatment with acetate ion. Hydrolysis of 6 and 11 yielded 7-hydroxymethyl-12-methylbenz[a]anthracene (7) and 5-fluoro-7-hydroxymethyl-12-methylbenz[a]anthracene (12), respectively. Since neither 11 nor 12 is appreciably carcinogenic, the carcinogenic metabolism of 7,12-dimethylbenz[a]anthracene (DMBA) probably does not involve attack at the 7-methyl group.

  DOI：

  10.1021/jm00208a013

文献信息

• NEWMAN M. S.; FIKES L. E.; HASHEM M. M.; KANNAN R.; SANKARAN V., J. MED. CHEM., 1978, 21, NO 10, 2076-2078
  作者：NEWMAN M. S.、 FIKES L. E.、 HASHEM M. M.、 KANNAN R.、 SANKARAN V.

  DOI：——

  日期：——
• Synthesis and carcinogenic activity of 5-fluoro-7-(oxygenated methyl)-12-methylbenz[a]anthracenes
  作者：Melvin S. Newman、Lewis E. Fikes、Mohamed M. Hashem、R. Kannan、V. Sankaran

  DOI：10.1021/jm00208a013

  日期：1978.10

  Treatment of 7,12-benz[a]anthraquinone (2) with methylmagnesium iodide or methyllithium yields mixtures of cis- and trans-7,12-dihydro-7,12-dihydroxy-7,12-dimethylbenz[a]anthracenes (3a,b), in which the ratio of cis to trans lies in the 3--4:1 region. Each isomer afforded high yields of 7-chloromethyl-12-methylbenz[a]anthracene (5) on treatment with hydrogen chloride in ethyl acetate. Similarly, 5-fluoro-7,12-benz[a]anthraquinone (8) afforded a mixture of cis- and trans-5-fluoro-7,12-dihydro-7,12-dihydroxy-7,12-dimethylbenz[a]anthracenes (9) which yielded 7-chloromethyl-5-fluoro-12-methylbenz[a]anthracene (10) on treatment with HCl. The chloromethyl compounds, 5 and 10, yielded 7-acetoxymethyl-12-methylbenz[a]anthracene (6) and 7-acetoxymethyl-5-fluoro-12-methylbenz[a]anthracene (11) on treatment with acetate ion. Hydrolysis of 6 and 11 yielded 7-hydroxymethyl-12-methylbenz[a]anthracene (7) and 5-fluoro-7-hydroxymethyl-12-methylbenz[a]anthracene (12), respectively. Since neither 11 nor 12 is appreciably carcinogenic, the carcinogenic metabolism of 7,12-dimethylbenz[a]anthracene (DMBA) probably does not involve attack at the 7-methyl group.