7-methoxy-9-hydroxy-3-methylbenzo[g]isoquinoline-5,10-dione | 126262-44-0

• 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-methoxy-9-hydroxy-3-methylbenzo[g]isoquinoline-5,10-dione
• 英文别名: 9-hydroxy-7-methoxy-3-methylbenzo[g]isoquinoline-5,10-dione；5-deoxybostrycoidin；6-deoxybostrycoidin
• CAS: 126262-44-0
• 化学式: C₁₅H₁₁NO₄
• 分子量: 269.257
• InChiKey: RGUUYFLCINGWMZ-UHFFFAOYSA-N

物化性质

• 熔点：
  193.8-194 °C
• 沸点：
  532.0±50.0 °C(Predicted)
• 密度：
  1.409±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  76.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-methoxy-9-hydroxy-3-methylbenzo[g]isoquinoline-5,10-dione 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 1.25h， 以87%的产率得到3-methyl-7,9-dihydroxybenzisoquinoline-5,10-dione
  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：

  7,9-dimethoxy-3-methylbenzoisoquinoline-5,10-quinone 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以93%的产率得到7-methoxy-9-hydroxy-3-methylbenzo[g]isoquinoline-5,10-dione
  参考文献：
  名称：

  Synthesis of Two Naphthoquinone Antibiotics, Dehydroherbarin and 6-Deoxybostrycoidin

  摘要：

  The synthesis of two naphthoquinone antibiotics, dehydroherbarin (7) and 6-deoxybostrycoidin (5), was accomplished by reaction of 3-acetonyl-2-bromomethyl-6,8-dimethoxy-1,4-naphthoquinone (23) with either triethylamine or ammonia, respectively. This is the first report on their synthesis.

  DOI：

  10.1021/jo990676g

文献信息

• Regioselective Synthesis of Benzo[g]isoquinoline-5,10-dione Derivatives as DNA Intercalators
  作者：Andreas Opitz、Ernst Roemer、Wolfgang Haas、Helmar Görls、Walter Werner、Udo Gräfe

  DOI：10.1016/s0040-4020(00)00186-1

  日期：2000.7

  We describe a new total synthesis for 9-(2-dimethylaminoethylamino)-6-hydroxy-7-methoxybenzo-[g]isoquinoline-5,10-dione (1) via cyclization and amination. Compound 1 acts as a DNA intercalator and inhibitor of gyrase and mammalian topoisomerase I and II. Preparation of the precursor heterocycle 2a can be accompanied by the Hayashi rearrangement, which is studied by semiempirical methods (AM1, PM3)

  我们描述了一种新的全合成的9-（2-二甲基氨基乙基氨基）-6-羟基-7-甲氧基苯并-[ g ]异喹啉-5,10-二酮（1）通过环化和胺化。化合物1充当DNA插入剂和回旋酶以及哺乳动物拓扑异构酶I和II的抑制剂。前体杂环2a的制备可以伴随Hayashi重排，通过半经验方法（AM1，PM3）对其进行研究。此外，通过异狄尔斯-阿尔德方法建立了取代苯并[ g ]异喹啉（例如，甲苯二cladin（3））的新的区域选择性途径。这些Diels–Alder反应的区域选择性是通过过渡态的半经验计算（AM1）预测的。
• Total synthesis of four naturally occurring 2-azaanthraquinone antibiotics, 6-deoxy-8-methylbostrycoidin, 6-deoxybostrycoidin, 7-O-demethyl-6-deoxybostrycoidin and scorpinone
  作者：Tuyen Nguyen Van、Guido Verniest、Sven Claessens、Norbert De Kimpe

  DOI：10.1016/j.tet.2005.01.035

  日期：2005.2

  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.
• Novel synthesis of the 2-azaanthraquinone alkaloid, scorpinone, based on two microwave-assisted pericyclic reactions
  作者：Tominari Choshi、Teppei Kumemura、Junko Nobuhiro、Satoshi Hibino

  DOI：10.1016/j.tetlet.2008.04.033

  日期：2008.6

  The total synthesis of the 2-azaanthraquinone alkaloid, scorpinone (4), isolated from the mycelium of a Bispora-like tropical fungus, has been completed in nine steps. The two key steps involve a microwave-assisted thermal electrocyclic reaction for the synthesis of an 8-oxygenated isoquinoline skeleton from a 1-aza 6 pi-hexatriene system, and a regioselective microwave- assisted [4+2] cycloaddition for the construction of a 2-azaanthraquinone framework. (C) 2008 Elsevier Ltd. All rights reserved.
• PARISOT, DENISE;DEVYS, MICHEL;BARBIER, MICHEL, Z. NATURFORSCH. B, 44,(1989) N1, C. 1473-1474
  作者：PARISOT, DENISE、DEVYS, MICHEL、BARBIER, MICHEL

  DOI：——

  日期：——
• Parisot, Denise; Devys, Michel; Barbier, Michel, Zeitschrift fur Naturforschung, B: Chemical Sciences, 1989, vol. 44, # 11, p. 1473 - 1474
  作者：Parisot, Denise、Devys, Michel、Barbier, Michel

  DOI：——

  日期：——