3-methyl-6H-benzophenanthrido-7,12-quin-5-one | 137057-04-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3-methyl-6H-benzophenanthrido-7,12-quin-5-one
• 英文别名: 1,8-Dihydroxy-3-methylbenzophenanthridine-5,7,12-trione；1,8-dihydroxy-3-methyl-6H-benzo[b]phenanthridine-5,7,12-trione
• CAS: 137057-04-6
• 化学式: C₁₈H₁₁NO₅
• 分子量: 321.289
• InChiKey: HBHVOCACNCVRBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 3-methyl-6H-benzophenanthrido-7,12-quin-5-one 在 硫酸 作用下， 反应 2.0h， 生成 Acetic acid 8-acetoxy-3-methyl-5,7,12-trioxo-5,6,7,12-tetrahydro-6-aza-benzo[a]anthracen-1-yl ester
  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：

  8-Hydroxy-1-methoxy-3-methylbenzophenanthridine-5,7,12-trione 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 3-methyl-6H-benzophenanthrido-7,12-quin-5-one
  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

• Synthesis of putative intermediates in the biosynthesis of the kinamycin antibiotics: total synthesis of phenanthroviridin aglycon and related compounds
  作者：Makarand P. Gore、Steven J. Gould、Dwight D. Weller

  DOI：10.1021/jo00036a005

  日期：1992.5

  Phenanthroviridin aglycon, 14, recently isolated from Streptomyces viridiochromogenes DSM 3972, and the corresponding pyridone 10 have been synthesized from the common intermediate (bromoaryl)naphthamide 42. This was prepared by condensation of a (trimethylsilyl)ethyl (bromoaryl)cinnamate 36 and a methoxy-substituted cyanophthalide anion 15, providing the ABD rings of the target benzo[b]phenanthridine skeleton. The aglycon 14 was obtained by a sequence of metal-halogen exchange and formylation, Hofmann rearrangement, cyclization, and deprotection. The pyridone was obtained by Hofmann rearrangement, metal-halogen exchange, cyclization, and deprotection. In addition, a route to cinnamate 36 via coumarin 49 was developed which would allow selective protection of the 1-hydroxyl group for synthesis of glycosidic analogues of phenanthroviridin, 13. The methodology developed is useful for preparation of 10, 14, and analogues specifically labeled at C-5 for study of biosynthesis of the kinamycin antibiotics.