2-Bromo-8-hydroxy-6-methoxy-1,4-naphthoquinone | 93564-97-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-Bromo-8-hydroxy-6-methoxy-1,4-naphthoquinone
• 英文别名: 3-bromo-5-hydroxy-7-methoxynaphthoquinone；2-bromo-8-hydroxy-6-methoxynaphthoquinone；2-Bromo-8-hydroxy-6-methoxynaphthalene-1,4-dione
• CAS: 93564-97-7
• 化学式: C₁₁H₇BrO₄
• 分子量: 283.078
• InChiKey: IKHDUGJSVIZXQH-UHFFFAOYSA-N

物化性质

• 沸点：
  484.1±45.0 °C(Predicted)
• 密度：
  1.799±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  四丁基锡 、 2-Bromo-8-hydroxy-6-methoxy-1,4-naphthoquinone 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以74%的产率得到
  参考文献：
  名称：

  Palladium-catalyzed coupling of 2-bromonaphthoquinones with stannanes: a concise synthesis of antibiotics WS 5995 A and C and related compounds

  摘要：

  The syntheses of antibiotics WS 5995 A and C and a hypothetical intermediate in the biosynthesis of the kinamycin antibiotics have been completed by using as the key step the palladium-catalyzed coupling of 2-bromo-1,4-naphthoquinones with stannanes.

  DOI：

  10.1021/jo00023a004
• 作为产物：
  描述：

  2,6-二溴对苯醌 、 (Z)-1-Ethoxy-3-methoxy-1-<(trimethylsilyl)oxy>-1,3-butadiene 以 苯 为溶剂， 反应 10.0h， 以45%的产率得到2-Bromo-8-hydroxy-6-methoxy-1,4-naphthoquinone
  参考文献：
  名称：

  Synthesis of Antibiotics WS 5995 A and C and Related Compounds by Palladium-Catalyzed Coupling of 2-Bromonaphthoquinones with Organostannanes

  摘要：

  The synthesis of arylnaphthoquinones can be performed simply by using as the key reaction the Pd(0)- and Cu(I)-catalyzed coupling of arylstannanes with 2-bromonaphthoquinones as the electrophiles. The palladium-catalyzed coupling reaction is general and allows for the functionalization of the unprotected quinone nucleus with alkyl, alkenyl, and aryl substituents. The coupling process tolerates the presence of a chelated peri hydroxyl and steric crowding of a 2,6-disubstituted arylstannane, although the preparation of a 2,6,2',6'-tetrasubstituted biaryl by coupling of 2-bromo-3,5-bis(acetyloxy)-1,4-naphthoquinone as the electrophile with 2,6-disubstituted arylstannanes was unsuccessful. The syntheses of quinonoid antibiotics WS 5995 A and C was accomplished by using this method as the key step. Benz[b]phenanthridinone 1, hypothetical intermediate in the biosynthesis of benz[b]phenanthridine alkaloids, was also prepared from antibiotic WS 5995 C or by addition of ammonia to the 2-aryl-1,4-naphthoquinone 41 followed by heterocyclization.

  DOI：

  10.1021/jo00099a045

文献信息

• Studies in anthracycline synthesis: simple Diels-Alder routes to pachybasin, .omega.-hydroxypachybasin, aloe-emodin, and fallacinol
  作者：Nicholas Benfaremo、Michael P. Cava

  DOI：10.1021/jo00201a033

  日期：1985.1