(+/-)-7.12c-dihydroxy-7r.12t-dimethyl-7.12-dihydro-benz[a]anthracene | 2518-00-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: (+/-)-7.12c-dihydroxy-7r.12t-dimethyl-7.12-dihydro-benz[a]anthracene
• 英文别名: (+/-)-7.12c-Dihydroxy-7r.12t-dimethyl-7.12-dihydro-benz[a]anthracen；Benz[a]anthracene-7,12-diol, 7,12-dihydro-7,12-dimethyl-, trans-；(7R,12R)-7,12-dimethylbenzo[a]anthracene-7,12-diol
• CAS: 2518-00-5；55125-18-3；55125-19-4
• 化学式: C₂₀H₁₈O₂
• 分子量: 290.362
• InChiKey: GJODVXBHWDFIDL-WOJBJXKFSA-N

物化性质

• 熔点：
  181.5-182.5 °C
• 沸点：
  508.3±45.0 °C(Predicted)
• 密度：
  1.256±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2906299090

反应信息

• 作为反应物：
  描述：

  (+/-)-7.12c-dihydroxy-7r.12t-dimethyl-7.12-dihydro-benz[a]anthracene 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 生成 7-氯甲基-12-甲基苯并(a)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：

  甲基碘化镁 、 苯并蒽-7,12-二酮 在 乙醚 、 苯 作用下， 生成 (+/-)-7.12c-dihydroxy-7r.12t-dimethyl-7.12-dihydro-benz[a]anthracene
  参考文献：
  名称：

  THE SYNTHESIS OF 5-PHENYL-9, 10-DIALKYL-9, 10-DIHYDROXY-9, 10-DIHYDRO-1, 2-BENZANTHRACENES AND RELATED COMPOUNDS^*

  摘要：

  DOI：

  10.1021/jo01225a005

文献信息

• Pheromone content of azinphosmethyl-susceptible and -resistant obliquebanded leafrollers (Lepidoptera: Tortricidae) as a function of time of day and female age
  作者：Ashraf M. El-Sayed、R.M. Trimble

  DOI：10.4039/ent134331-3

  日期：2002.6

  The effect of time of day and age on the amounts and ratios of four pheromone compounds [(Z)-11-tetradecenyl acetate (Z11-14:Ac), (E)-11-tetradecenyl acetate (E11-14:Ac), (Z)-11-tetradecenol (Z11-14:OH), and (Z)-11-tetradecenal (Z11-14:Al)] was compared in azinphosmethyl-susceptible (susceptible) and -resistant (resistant) female obliquebanded leafrollers, Choristoneura rosaceana (Harris). The amounts of all four pheromone compounds varied during the hour before and five hours after the onset of scotophase. The glands of resistant females contained approximately one half the amount of Z11-14:Ac and Z11-14:OH as the glands of susceptible females during the second and third hours of scotophase, and between 50 and 70% as much Z11-14:Al as the glands of susceptible females during the hour before and second to fourth hours of scotophase. The glands of susceptible and resistant females contained similar amounts of E11-14:Ac. The relative amounts of each of the four pheromone compounds were affected by time of day but not by resistance status. There was a negative linear relationship between the amounts of each of the four compounds and female age in both types of females. The amounts of Z11-14:Ac and E11-14:Ac declined at similar rates with age in susceptible and resistant females; the amounts of Z11-14:OH and Z11-14:Al declined more rapidly with age in susceptible than in resistant females. The relative amounts of the four compounds were not affected by female age. Temporal variation in the relative amounts of pheromone in susceptible and resistant C. rosaceana may be associated with similar variation in the emission of pheromone and corresponding temporal variation in the relative attractiveness of the two types of females.

  摘要 比较了一天中的时间和年龄对四种信息素化合物[(Z)-11-十四烯基乙酸酯（Z11-14:Ac）、(E)-11-十四烯基乙酸酯（E11-14:Ac）、(Z)-11-十四烯醇（Z11-14：OH）和 (Z)-11-十四烯醛（Z11-14:Al）]进行了比较。所有四种信息素化合物的含量在光照开始前一小时和光照开始后五小时内各不相同。在光斑期的第二和第三小时，抗性雌虫腺体中 Z11-14:Ac 和 Z11-14:OH 的含量约为易感雌虫腺体的一半；在光斑期开始前一小时和第二至第四小时，抗性雌虫腺体中 Z11-14:Al 的含量约为易感雌虫腺体的 50% 至 70%。易感雌虫和抗性雌虫腺体中的 E11-14:Ac 含量相似。四种信息素化合物的相对含量受一天中时间的影响，但不受抗性状态的影响。两种雌虫的四种化合物的含量与雌虫的年龄呈负线性关系。在易感雌性和抗性雌性中，Z11-14:Ac和E11-14:Ac的含量随年龄下降的速度相似；在易感雌性中，Z11-14:OH和Z11-14:Al的含量随年龄下降的速度比抗性雌性快。四种化合物的相对含量不受雌性年龄的影响。易感性和抗性蔷薇雌虫信息素相对含量的时间变化可能与信息素释放量的相似变化以及两种雌虫相对吸引力的相应时间变化有关。
• 474. Substituted anthracene derivatives. Part III. Further examples of 1 : 5-anionotropic rearrangements
  作者：G. M. Badger、R. S. Pearce

  DOI：10.1039/jr9500002314

  日期：——
• 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：——
• THE SYNTHESIS OF 5-PHENYL-9, 10-DIALKYL-9, 10-DIHYDROXY-9, 10-DIHYDRO-1, 2-BENZANTHRACENES AND RELATED COMPOUNDS^*
  作者：W. E. BACHMANN、JAMES T. BRADBURY

  DOI：10.1021/jo01225a005

  日期：1937.5
• 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.