2,5,8-trihydroxy-1,4-naphthoquinone | 13379-22-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,5,8-trihydroxy-1,4-naphthoquinone
• 英文别名: 2,5,8-trihydroxynaphthalene-1,4-dione；2-hydroxynaphthazarine；2-hydroxynaphthazarin；naphthopurpurin；2,5,8-trihydroxy-[1,4]naphthoquinone；2,5,8-Trihydroxy-[1,4]naphthochinon
• CAS: 13379-22-1
• 化学式: C₁₀H₆O₅
• 分子量: 206.155
• InChiKey: ZFXYVCPRQYVJDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.92
• 重原子数：
  15.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  94.83
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2,5,8-trihydroxy-1,4-naphthoquinone 在 四乙酰基二硼氧烷 、 potassium hydrogencarbonate 作用下， 以 乙腈 、 苯 为溶剂， 反应 25.0h， 生成 1,4-二羟基-2-甲氧基-7-甲基蒽-9,10-二酮
  参考文献：
  名称：

  Burns, Christopher J.; Gill, Melvyn, Australian Journal of Chemistry, 1991, vol. 44, # 10, p. 1447 - 1458

  摘要：

  DOI：
• 作为产物：
  描述：

  5,8-二羟基-2-甲氧基-1,4-萘醌 在 盐酸 作用下， 生成 2,5,8-trihydroxy-1,4-naphthoquinone
  参考文献：
  名称：

  Bekaert, Alain; Andrieux, Jean; Plat, Michel, Bulletin de la Societe Chimique de France, 1986, # 2, p. 314 - 316

  摘要：

  DOI：

文献信息

• Chemistry of naphthazarin derivatives 13. Conformational analysis of 3-(alk-1-enyl)-2-hydroxy-1,4-naphthoquinones by quantum chemistry methods
  作者：V. P. Glazunov、D. V. Berdyshev、A. Ya. Yakubovskaya、N. D. Pokhilo

  DOI：10.1007/s11172-006-0480-z

  日期：2006.10

  The molecular structures of various conformers of 2-hydroxy-1,4-naphthoquinone; 3-(alk-1-enyl)-2-hydroxy-1,4-naphthoquinones; 2,5,8-trihydroxy-1,4-naphthoquinone; and 3-(alk-1-enyl)-2,5,8-trihydroxy-1,4-naphthoquinones were studied by density functional theory (B3LYP/6-31(d), B3LYP/6-31(d, p)) and ab initio (MP2/6-31G, MP2/6-31(d)) methods. The strengths of the intramolecular hydrogen bonds formed by the β-hydroxy group with the O atom at C(1) and with the double bond π-electrons of the alkenyl substituents in the quinonoid rings were estimated. The compounds studied mainly exist as rotamers with the former-type hydrogen bonds. The splitting of the quinonoid bands of the stretching vibrations of the β-hydroxy group in the IR spectra of 3-(alk-1-enyl)-2-hydroxy-1,4-naphthoquinones and 3-(alk-1-enyl)-2,5,8-trihydroxy-1,4-naphthoquinones in hexane solutions is due to the existence of rotamers formed upon internal rotation of the alkenyl substituent.

  通过密度泛函理论 (B3LYP/6-31(d), B3LYP/6-31(d, p)) 和从头算 (MP2/6-31G, MP2/6-31(d)) 方法研究了2-羟基-1,4-萘醌、3-(链烯-1-基)-2-羟基-1,4-萘醌、2,5,8-三羟基-1,4-萘醌和3-(链烯-1-基)-2,5,8-三羟基-1,4-萘醌的各种构象分子的分子结构。估算了β-羟基与C(1)位氧原子及与醌环上链烯基取代基双键π电子形成的分子内氢键的强度。所研究的化合物主要以形成前一种类型氢键的旋转异构体形式存在。3-(链烯-1-基)-2-羟基-1,4-萘醌和3-(链烯-1-基)-2,5,8-三羟基-1,4-萘醌在己烷溶液中的红外光谱中β-羟基伸缩振动的醌带分裂是由于链烯基取代基内旋转形成的旋转异构体存在所致。
• [EN] NAPTHOQUINONES, PRO-DRUGS, AND METHODS OF USE THEREOF<br/>[FR] NAPHTOQUINONES, PROMÉDICAMENTS, ET LEURS PROCÉDÉS D'UTILISATION
  申请人：UNIV TEXAS

  公开号：WO2017106624A1

  公开（公告）日：2017-06-22

  Provided herein are naphthoquinones compounds such as those with a hydrogen bond donating group of the formula (I): wherein: R1, R2, R3, R4, R5, and n are as defined herein. Also provided herein are pharmaceutical composition of the present compounds and methods of treatment using the compounds including their use in the treatment of cancer.

  提供在本说明书中的萘醌化合物，例如具有式(I)中的氢键供体基团的那些：其中：R1、R2、R3、R4、R5和n如本文所述定义。此外，还提供了本化合物的药物组合物以及使用这些化合物进行治疗的方法，包括它们在癌症治疗中的应用。
• Electronic spectra of substituted naphthoquinones
  作者：I. Singh、R.T. Ogata、R.E. Moore、C.W.J. Chang、P.J. Scheuer

  DOI：10.1016/s0040-4020(01)90989-5

  日期：1968.1

  aid to structural elucidation of these compounds the electronic spectra of a large number of substituted naphthoquinones were examined. The bands in the 240–600 mμ region of the electronic spectra of 1,4-naphthoquinone, juglone, and naphthazarin have been assigned to either benzenoid or quinoid electronic excitations and the effect of substitution on the position of these bands has been systematically

  棘皮动物基于萘醌骨架精心构造了许多紧密相关的结构颜料（spinochromes）。为了阐明这些化合物，对大量取代的萘醌的电子光谱进行了研究。1,4-萘醌，ju酮和萘达沙林的电子光谱中240-600mμ范围内的谱带已被分配给苯类或醌型电子激发，并且已经系统地研究了取代对这些谱带位置的影响。结果，已经得出了许多经验相关性，这些经验相关性可用于未知颜料的结构确定。
• 1,4-Conjugate addition of 2-hydroxynaphthazarins to acyclic and cyclic α,β-unsaturated ketones. Prototropic ring-chain tautomerism of the adducts
  作者：N. N. Balaneva、O. S. Radchenko、V. P. Glazunov、V. L. Novikov

  DOI：10.1007/s11172-012-0264-6

  日期：2012.10

  TsOH-Catalyzed reactions of 6,7-disubstituted 2-hydroxynaphthazarins and acyclic or cyclic α,β-enones afforded the corresponding Michael-type adducts, viz., 3-substituted naphthazarins in 17–78% yields. 1H and 13C NMR and IR spectroscopy showed that the adducts with cyclohexenone and methyl vinyl ketone exist in CDCl3 solutions as mixtures of open-chain and cyclic tautomers, whereas the adducts with

  TsOH 催化 6,7-二取代的 2-羟基萘并与无环或环状 α,β-烯酮反应得到相应的迈克尔型加合物，即 3-取代的萘并以 17-78% 的产率产生。1H 和 13C NMR 和 IR 光谱表明，与环己烯酮和甲基乙烯基酮的加合物以开链和环状互变异构体的混合物形式存在于 CDCl3 溶液中，而与环戊烯酮的加合物仅以开链形式存在。
• The Reductive Dehalogenation of Halo-Substituted Naphthazarins and Quinizarins as a Simple Route to Parent Compounds
  作者：Victor Ph. Anufriev、Galina V. Malinovskaya、Vyacheslav L. Novikov、Nadezhda N. Balanyova、Sergey G. Polonik

  DOI：10.1080/00397919808007029

  日期：1998.6

  Abstract By the reaction of 2-chloro-3-alkyl-, 2,3-dichloro(dibromo)-, trichloro-(tribromo)-and tetrachloro(tetrabromo)-naphthazarins and 2,3-dichloroquinizarin with Fe/HOAc followed by oxidation with an air in a mild basic conditions the corresponding naphthazarins and quinizarin were obtained in good to excellent yields.

  摘要 通过 2-氯-3-烷基-、2,3-二氯（二溴）-、三氯-（三溴）-和四氯（四溴）-萘并和 2,3-二氯喹吖啶与 Fe/HOAc 反应，然后氧化在温和碱性条件下的空气中，以良好至极好的收率获得了相应的萘并芴素。

表征谱图