2-溴-5,8-二羟基萘-1,4-二酮 | 78226-78-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2-溴-5,8-二羟基萘-1,4-二酮
• 英文名称: 2-bromo-5,8-dihydroxy-1,4-dihydronaphthalene-1,4-dione
• 英文别名: 2-bromo-5,8-dihydroxy-1,4-naphthoquinone；bromo-2 dihydroxy-5,8 naphtoquinone-1,4；2-bromonaphthazarine；Bromnaphthazarin；2-bromo-5,8-dihydroxy-[1,4]naphthoquinone；2-Brom-5,8-dihydroxy-[1,4]naphthochinon；6-Bromo-5,8-dihydroxy-1,4-naphthalenedione；2-bromo-5,8-dihydroxynaphthalene-1,4-dione
• CAS: 78226-78-5
• 化学式: C₁₀H₅BrO₄
• 分子量: 269.051
• InChiKey: IBKXPWMILRITGB-UHFFFAOYSA-N

物化性质

• 熔点：
  189-192 °C(Solv: hexane (110-54-3); acetone (67-64-1))
• 沸点：
  504.5±50.0 °C(Predicted)
• 密度：
  2.041±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-溴-5,8-二羟基萘-1,4-二酮 在 palladium on activated charcoal 盐酸 、 air 、 氢气 作用下， 以 乙醚 为溶剂， 反应 1.75h， 生成 N-(5,8-dihydroxy-1,4-naphthoquinone-2-yl)piperidine
  参考文献：
  名称：

  有效合成（烷基氨基）萘醌的一般程序。

  摘要：

  萘并萘，朱酮和萘醌的烷基氨基衍生物已经通过其相应的溴类似物以高收率合成，特别是在萘他林的情况下。

  DOI：

  10.1021/jo9517252
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 乙醇 作用下， 生成 2-溴-5,8-二羟基萘-1,4-二酮
  参考文献：
  名称：

  Wheeler; Edwards, Journal of the American Chemical Society, 1917, vol. 39, p. 2466

  摘要：

  DOI：

文献信息

• Synthesis and biological evaluation of novel (l)-α-amino acid methyl ester, heteroalkyl, and aryl substituted 1,4-naphthoquinone derivatives as antifungal and antibacterial agents
  作者：Vishnu K. Tandon、Dharmendra B. Yadav、Ravindra V. Singh、Ashok K. Chaturvedi、Praveen K. Shukla

  DOI：10.1016/j.bmcl.2005.08.032

  日期：2005.12

  A series of (S)-N-(1,4-naphthoquinon-2-yl)-alpha-amino acid methyl esters 3-9, 2-N,N-dialkylamino-1,4-naphthoquinones 10-11 and 2-hydroxy-3-(2'-mercaptoimidazolyl)-1,4-naphthoquinones and their cyclic analogs 12-15 were synthesized and evaluated for antifungal and antibacterial activities. The structure-activity relationships of these compounds were studied and the results show that the compounds 9b

  一系列的（S）-N-（1,4-萘醌-2-基）-α-氨基酸甲酯3-9，2-N，N-二烷基氨基-1,4-萘醌10-11和2-合成了羟基-3-（2'-巯基咪唑基）-1,4-萘醌及其环状类似物12-15，并评估了其抗真菌和抗菌活性。研究了这些化合物的结构活性关系，结果表明化合物9b和13c对白色念珠菌，新隐球菌和schenothrix schenckii表现出体外抗真菌活性，而化合物6a对粪便链球菌K表现出体外抗菌活性。肺炎，大肠埃希菌和金黄色葡萄球菌。
• Heteroannulation of naphthoquinones. Studies on the reaction of 2-bromo-2,3-dihydronaphthoquinone derivatives with 1,2-binucleophiles.
  作者：Elias A. Couladouros、Zoi F. Plyta、Theodoros Iliadis、Vassilios Roussis、Vassilios P. Papageorgiou

  DOI：10.1002/jhet.5570330331

  日期：1996.5

  Heterocyclic derivatives of naphthoquinones were synthesized via their 2-bromo-2,3-dehydro-intermediates. This new route may lead to the formation of benzo[a]phenothiazin-5-ones, benzo[f]quinoxalin-6-ones as well as their 1,4 (or 7,10) dihydroxy-derivatives in high yields. The possible mechanisms involved in the formation of these compounds are discussed.

  萘醌的杂环衍生物是通过它们的2-溴-2,3-脱氢中间体合成的。这种新途径可能导致高产率地形成苯并[ a ]吩噻嗪-5-酮，苯并[ f ]喹喔啉-6-酮及其1,4（或7,10）二羟基衍生物。讨论了涉及这些化合物形成的可能机理。
• Synthesis, antibacterial and antifungal activities of naphthoquinone derivatives: a structure–activity relationship study
  作者：Juan M. Sánchez-Calvo、Gara R. Barbero、Guillermo Guerrero-Vásquez、Alexandra G. Durán、Mariola Macías、Manuel A. Rodríguez-Iglesias、José M. G. Molinillo、Francisco A. Macías

  DOI：10.1007/s00044-016-1550-x

  日期：2016.6

  4-naphthoquinone presented strong activity, e.g., 2-bromo-5-hydroxy-1,4-naphthoquinone, which exhibited inhibition at an MIC of 16 µg/mL in S. aureus, and 2-chloro-5,8-dihydroxy-1,4-naphthoquinone, with an MIC of 2 µg/mL in C. krusei. These compounds showed higher activity against fungi, but the antibacterial activities were very low. The study of structure–activity relationships is very important in the search

  1,4-萘醌衍生物的合成备受关注，因为这些化合物作为抗疟疾，抗菌，抗真菌和抗癌剂具有很强的活性。合成了一系列50种萘醌衍生物，并使用肉汤微稀释法评估了其对大肠杆菌，铜绿假单胞菌，粪肠球菌，金黄色葡萄球菌，克鲁斯假丝酵母，副念珠菌和新隐球菌的抗菌和抗真菌活性。该念珠菌种是最易感的微生物。1,4-萘醌的卤素衍生物具有很强的活性，例如2-溴-5-羟基-1,4-萘醌，在金黄色葡萄球菌和2-chloro-5中的MIC为16 µg / mL时表现出抑制作用，8-二羟基-1,4-萘醌，在克鲁氏梭菌中的MIC为2 µg / mL 。这些化合物显示出较高的抗真菌活性，但抗菌活性非常低。由于药库的限制，结构-活性关系的研究对于寻找新的抗微生物药物非常重要。
• Chemistry of naphthazarin derivatives: XV. Bromination of naphthazarin and its derivatives
  作者：N. D. Pokhilo、A. Ya. Yakubovskaya、V. P. Glazunov

  DOI：10.1134/s1070428011040063

  日期：2011.4

  Bromination of a number of naphthazarin (5,8-dihydroxy-1,4-naphthoquinone) derivatives having different substituents in the aromatic ring with molecular bromine in carbon tetrachloride was studied. Preparative procedures for the synthesis of 2-bromo-5,8-dihydroxy-7-methoxy-1,4-naphthoquinone, 2-bromo-6,7-dichloro-5,8-dihydroxy-1,4-naphthoquinone, 2-bromo-3,5,8-trihydroxy-1,4-naphthoquinone, and 2-bromo-6

  研究了在四氯化碳中用分子溴溴化许多在芳环上具有不同取代基的萘他沙林（5,8-二羟基-1,4-萘醌）衍生物的方法。合成2-溴-5,8-二羟基-7-甲氧基-1,4-萘醌，2-溴-6,7-二氯-5,8-二羟基-1,4-萘醌，2-的制备方法开发了溴3,5,8-三羟基-1,4-萘醌和2-溴-6,7-二氯-3,5,8-三羟基-1,4-萘醌。
• PROCESS FOR PRODUCING BLACK COLORANT, COSMETIC CONTAINING SAID COLORANT, AND APPLICATION THEREOF
  申请人：IHARA CHEMICAL INDUSTRY CO., LTD.

  公开号：EP0500942A1

  公开（公告）日：1992-09-02

  A process for producing a black colorant which comprises treating finely powdered amino sugar, protein or polyamide with a naphthoquinone derivative of general formula (1); a cosmetic containing a black colorant thus produced; and a process for coloring a base material with this colorant. In the said formula, R₁ represents hydrogen, hydroxy, halogen, α or β ; R₂ represents hydrogen or hydroxy; R₃ represents alkyl, alkenyl, or hydroxyalkyl: and n is 1 or 2.

  一种生产黑色着色剂的工艺，包括用通式(1)的萘醌衍生物处理细粉末状的氨基糖、蛋白质或聚酰胺；一种含有由此生产的黑色着色剂的化妆品；以及一种用该着色剂给基底材料着色的工艺。在上述通式中，R₁代表氢、羟基、卤素、α 或 β；R₂代表氢或羟基；R₃代表烷基、烯基或羟基烷基：n 为 1 或 2。