9-methoxy-2-azaanthra-5,10-quinone | 90381-63-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 9-methoxy-2-azaanthra-5,10-quinone
• 英文别名: 5-methoxy-2-azaanthracene-9,10-dione；9-Methoxybenzo[g]isoquinoline-5,10-dione
• CAS: 90381-63-8
• 化学式: C₁₄H₉NO₃
• 分子量: 239.23
• InChiKey: YGNXLFRYNTXWCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  56.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9-methoxy-2-azaanthra-5,10-quinone 在 三溴化硼 作用下， 以78%的产率得到9-hydroxy-benzo[g]isoquinoline-5,10-dione
  参考文献：
  名称：

  Structure–activity relations of azafluorenone and azaanthraquinone as antimicrobial compounds

  摘要：

  Antimicrobial activities of two azafluorenones, four 1-azaanthraquinones, five 2-azaanthraquinones, and one 2-azaquinone were tested. Several azaanthraquinones possessed broad, potent activity, while the azafluorenones demonstrated weak activity. The following structure-activity relationship was postulated: (1) activity decreased in the order 2-azaanthraquinones >1-azaanthraquinones > azafluorenones; and (2) a hydroxyl group at the peri-carbonyl group enhanced activity. In addition, correlations among reduction potential, hydrophobic parameter, and antimicrobial activity were discussed. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.059
• 作为产物：
  描述：

  12-Methoxy-6-azatetracyclo[10.2.2.02,11.04,9]hexadeca-2(11),4(9),5,7,13-pentaene-3,10-dione 生成 9-methoxy-2-azaanthra-5,10-quinone
  参考文献：
  名称：

  POTTS K. T.; BHATTACHARJEE D.; WALSH E. B., J. ORG. CHEM., 51,(1986) N 11, 2011-2021

  摘要：

  DOI：

文献信息

• Regiochemical control in Diels–Alder routes to aza-anthraquinone derivatives
  作者：Kevin T. Potts、Debkumar Bhattacharjee、Eileen B. Walsh

  DOI：10.1039/c39840000114

  日期：——

  Quinoline- and isoquinoline-5,8-diones react with 1-methoxycyclohexa-1,3-diene at 80 °C, the former giving 8-methoxy-1-aza-anthraquinone regiospecifically and the latter 5-methoxy-2-aza-anthraquinone regioselectively; in similar cycloadditions, substituted naphtho- and azanaphtho-quinones react with 1-dimethylamino-3-methyl-1-azabuta-1,3-diene at room temperature forming substituted mono- and di-aza-anthraquinones

  喹啉和异喹啉-5,8-二烯与1-甲氧基环己-1,3-二烯在80°C下反应，前者在区域特异性地产生8-甲氧基-1-氮杂-蒽醌，后者5-甲氧基-2-氮杂-蒽醌区域选择性；在类似的环加成反应中，取代的萘醌和氮杂萘醌在室温下与1-二甲基氨基-3-甲基-1-氮杂-1，3-二烯反应，以高收率和高选择性形成取代的单-和二-氮杂-蒽醌。
• Cycloaddition routes to azaanthraquinone derivatives. 1. Use of azadienophiles
  作者：kevin T. Potts、Debkumar Bhattacharjee、Eileen B. Walsh

  DOI：10.1021/jo00361a014

  日期：1986.5
• Khanapure, Subhash P.; Biehl, Edward R., Heterocycles, 1988, vol. 27, # 11, p. 2643 - 2650
  作者：Khanapure, Subhash P.、Biehl, Edward R.

  DOI：——

  日期：——