5-Hydroxy-2-<2-(4,5-dihydropyranyl)>-1,4-naphthoquinone | 137039-29-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-Hydroxy-2-<2-(4,5-dihydropyranyl)>-1,4-naphthoquinone
• 英文别名: 2-(3,4-dihydro-2H-pyran-6-yl)-5-hydroxynaphthalene-1,4-dione
• CAS: 137039-29-3
• 化学式: C₁₅H₁₂O₄
• 分子量: 256.258
• InChiKey: LTMKLDYFEPLMAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-羟基胡桃醌 在 tris-(dibenzylideneacetone)dipalladium(0) 2,6-二甲基吡啶 、 N-甲基吡咯烷酮 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 19.0h， 生成 5-Hydroxy-2-<2-(4,5-dihydropyranyl)>-1,4-naphthoquinone
  参考文献：
  名称：

  Palladium-Catalyzed Coupling of Naphthoquinone Triflates with Stannanes. Unprecedented Nucleophilic Aromatic Substitution on a Hydroxynaphthoquinone Triflate

  摘要：

  DOI：

  10.1021/jo9621027

文献信息

• Synthesis of Antibiotics WS 5995 A and C and Related Compounds by Palladium-Catalyzed Coupling of 2-Bromonaphthoquinones with Organostannanes
  作者：Antonio M. Echavarren、Nuria Tamayo、Diego J. Cardenas

  DOI：10.1021/jo00099a045

  日期：1994.10

  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.
• Palladium-catalyzed coupling of 2-bromonaphthoquinones with stannanes: a concise synthesis of antibiotics WS 5995 A and C and related compounds
  作者：Nuria Tamayo、Antonio M. Echavarren、M. Carmen Paredes

  DOI：10.1021/jo00023a004

  日期：1991.11

  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.
• Palladium-Catalyzed Coupling of Naphthoquinone Triflates with Stannanes. Unprecedented Nucleophilic Aromatic Substitution on a Hydroxynaphthoquinone Triflate
  作者：Antonio M. Echavarren、Óscar de Frutos、Nuria Tamayo、Pedro Noheda、Paloma Calle

  DOI：10.1021/jo9621027

  日期：1997.6.1