7,9-dimethoxy-3-methylbenzoisoquinoline-5,10-quinone | 77794-86-6

• 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: 7,9-dimethoxy-3-methylbenzoisoquinoline-5,10-quinone
• 英文别名: 7,9-dimethoxy-3-methylbenzoisoquinoline-5,10-dione；3-methyl-7,9-dimethoxybenzisoquinoline-5,10-dione；7,9-dimethoxy-3-methylbenzo[g]isoquinoline-5,10-dione；7,9-dimethoxy-3-methylbenz[g]isoquinoline-5,10-dione；3-methyl-6,8-dimethoxy-2-aza-9,10-anthraquinone；scorpinone
• CAS: 77794-86-6
• 化学式: C₁₆H₁₃NO₄
• 分子量: 283.284
• InChiKey: ZEJGLXXBAAPUPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  65.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7,9-dimethoxy-3-methylbenzoisoquinoline-5,10-quinone 在 水 作用下， 以 乙腈 为溶剂， 以55%的产率得到6-hydroxy-7,9-dimethoxy-3-methylbenzoisoquinoline-5,10-quinone
  参考文献：
  名称：

  Krapcho, A. Paul; Waterhouse, David J., Heterocycles, 1999, vol. 51, # 4, p. 737 - 750

  摘要：

  DOI：
• 作为产物：
  描述：

  2-acetonyl-5,7-dimethoxy-3-(phenoxymethyl)naphthoquinone 在 air 、 氨 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 以81%的产率得到7,9-dimethoxy-3-methylbenzoisoquinoline-5,10-quinone
  参考文献：
  名称：

  Total synthesis of four naturally occurring 2-azaanthraquinone antibiotics, 6-deoxy-8-methylbostrycoidin, 6-deoxybostrycoidin, 7-O-demethyl-6-deoxybostrycoidin and scorpinone

  摘要：

  A total synthesis of four natural 2-azaanthraquinones, 6-deoxy-8-methylbostrycoidin, 6-deoxybostrycoidin, 7-0-demethyl-6-deoxybostrycoidin and scorpinone was accomplished using an optimized procedure for 2-azaanthraquinone synthesis, involving a [4+2]-cycloaddition protocol, of a polyoxygenated diene with a suitably functionalized benzoquinone, acetonylation with pyridinium ylids, cyclisation with ammonia and O-demethylation with boron(III) bromide. 2-Azaanthraquinones are rarely found in nature and reveal interesting physiological properties. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.01.035

文献信息

• Cameron, Donald W.; Deutscher, Kenneth R.; Feutrill, Geoffrey I., Australian Journal of Chemistry, 1982, vol. 35, # 7, p. 1439 - 1450
  作者：Cameron, Donald W.、Deutscher, Kenneth R.、Feutrill, Geoffrey I.

  DOI：——

  日期：——
• Novel Total Synthesis of the 2-Azaanthraquinone Alkaloid Scorpinone Using a Tandem Oxidation and Azaelectrocyclic Reaction
  作者：Satoshi Hibino、Tominari Choshi、Miharu Hironaka、Miki Goto、Kaori Shimizu、Yuhki Kurata、Takashi Nishiyama、Noriyuki Hatae

  DOI：10.3987/com-14-13155

  日期：——

  A new tandem oxidation and electrocyclic reaction of a 1-aza 6 pi-electron system derived from a known 3-hydroxynaphthalene derivative was developed for the synthesis of 2-azaanthraquinones. Total synthesis of scorpinone (1a) was achieved in seven steps using this new tandem reaction. In addition, the positional isomer, 7,9-dimethoxy-4-methylbenzo[g]isoquinoline-5,10-dione (1b) was also synthesized in the same way.
• Cameron, Donald W.; Deutscher, Kenneth R.; Feutrill, Geoffrey I., Australian Journal of Chemistry, 1982, vol. 35, # 7, p. 1451 - 1468
  作者：Cameron, Donald W.、Deutscher, Kenneth R.、Feutrill, Geoffrey I.、Hunt, Dianne E.

  DOI：——

  日期：——
• Synthesis of bostrycoidin and 8-0-methylbostrycoidin
  作者：Donald W. Cameron、Kenneth R. Deutscher、Geoffrey I. Feutrill

  DOI：10.1016/s0040-4039(00)71142-7

  日期：1980.1
• Deshpande; Khan; Ayyangar, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 9, p. 965 - 966
  作者：Deshpande、Khan、Ayyangar

  DOI：——

  日期：——

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