2-acetyl-5,8-dihydroxy-1,4-naphthoquinone | 17559-94-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-acetyl-5,8-dihydroxy-1,4-naphthoquinone
• 英文别名: 2-Acetyl-naphthazarin；2-acetyl-5,8-dihydroxynaphthalene-1,4-dione
• CAS: 17559-94-3
• 化学式: C₁₂H₈O₅
• 分子量: 232.193
• InChiKey: UQMNZXPWZLRICY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  91.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-乙基-5,8-二羟基-1,4-萘醌 在 溴 作用下， 以 四氯化碳 为溶剂， 反应 24.0h， 以1%的产率得到2-acetyl-5,8-dihydroxy-1,4-naphthoquinone
  参考文献：
  名称：

  萘萘胺衍生物的化学：XIV。1'-溴代烷基萘他扎林的制备合成

  摘要：

  A reaction of alkylnaphthazarines with bromine in tetrachloromethane was investigated. A preparative synthesis was developed for substituted 1'-bromoalkylnaphthazarines, and based on the substance 1'-hydroxyalkylnaphthazarines were prepared, analogs of shikalkin, a racemic mixture of plant pigments from Boraginaceae family. 2-Acyl-3-hydroxynaphthazarine was synthesized, a minor metabolite of urchin from genus Echinothrix.

  DOI：

  10.1134/s1070428007080143

文献信息

• Spinochrome synthesis
  作者：I. Singh、R.E. Moore、C.W.J. Chang、R.T. Ogata、P.J. Scheuer

  DOI：10.1016/s0040-4020(01)98704-6

  日期：1968.1

  widely distributed structural pigments of the sea urchins (echinoids) one (spinochrome B) is a derivative of juglone, while four (spinochromes A, C, D, and E) are derivatives of naphthazarin. In addition to the two peri OH groups of naphthazarin these compounds bear one or more β-hydroxyls and/or an acetyl side chain. The synthesis of these four naphthazarin derivatives is described. The naphthalene skeleton

  在海胆的五种广泛分布的结构性颜料（类神经碱）中，一种（螺闪体色素B）是朱古龙的衍生物，而四种（螺闪体色素A，C，D和E）是萘甲萘林的衍生物。除了这两个围萘他沙林的OH基团带有一个或多个β-羟基和/或乙酰基侧链。描述了这四种萘他林衍生物的合成。萘骨架是通过将1,2-二羟基-3,4-二甲氧基苯与氯-或二氯马来酸酐在铝-氯化钠熔体中缩合而构建的。通过用甲醇盐离子的亲核取代氯或通过Thiele方法引入了更多的氧官能团。通过制备无色乙酸酯并将其用乙酸酐-三氟化硼处理，将乙酰基侧链连接至聚羟基萘醌。在加工过程中水解和氧化后，萘扎林体系得以再生。
• Chemistry of naphthazarine derivatives: XIV. Preparative synthesis of 1′-bromoalkylnaphthazarines
  作者：N. D. Pokhilo、A. Ya. Yakubovskaya、V. F. Anufriev、D. V. Berdyshev

  DOI：10.1134/s1070428007080143

  日期：2007.8

  A reaction of alkylnaphthazarines with bromine in tetrachloromethane was investigated. A preparative synthesis was developed for substituted 1'-bromoalkylnaphthazarines, and based on the substance 1'-hydroxyalkylnaphthazarines were prepared, analogs of shikalkin, a racemic mixture of plant pigments from Boraginaceae family. 2-Acyl-3-hydroxynaphthazarine was synthesized, a minor metabolite of urchin from genus Echinothrix.