2,5,8-trihydroxy-6,7-dichloro-3-ethyl-1,4-naphthoquinone | 187149-22-0

• 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-6,7-dichloro-3-ethyl-1,4-naphthoquinone
• 英文别名: 6,7-dichloro-3-ethyl-2,5,8-trihydroxy-1,4-naphthoquinone；2-hydroxy-6,7-dichloro-3-ethylnaphthazarin；6,7-dichloro-3-ethyl-2-hydroxynaphthazarin
• CAS: 187149-22-0
• 化学式: C₁₂H₈Cl₂O₅
• 分子量: 303.099
• InChiKey: HTTYYYQEIIVFHL-UHFFFAOYSA-N

物化性质

• 熔点：
  156-158 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  564.5±50.0 °C(Predicted)
• 密度：
  1.743±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.01
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 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-6,7-dichloro-3-ethyl-1,4-naphthoquinone 在 aluminum oxide 、 三氯化铝 、 cesium fluoride 作用下， 以 硝基苯 为溶剂， 反应 15.0h， 生成 2-Ethyl-3,5,6,7,8-pentahydroxy-1,4-naphthoquinone
  参考文献：
  名称：

  Synthesis of some hydroxynaphthazarins and their cardioprotective effects under ischemia-reperfusion in vivo

  摘要：

  A series of hydroxynaphthazarins has been synthesized. Some of them were found in in vivo experiments to be protectors of myocardium under ischemia-reperfusion and to reduce the infarction zone by 50% without any adverse effect. All compounds exhibit a moderate or small toxicity and are active in low doses. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00075-4
• 作为产物：
  描述：

  2,3-dichloro-5,8-dihydroxy-[1,4]naphthoquinone 在 manganese(IV) oxide 、 硫酸 作用下， 以 叔丁醇 为溶剂， 反应 2.0h， 生成 2,5,8-trihydroxy-6,7-dichloro-3-ethyl-1,4-naphthoquinone
  参考文献：
  名称：

  Synthesis of some hydroxynaphthazarins and their cardioprotective effects under ischemia-reperfusion in vivo

  摘要：

  A series of hydroxynaphthazarins has been synthesized. Some of them were found in in vivo experiments to be protectors of myocardium under ischemia-reperfusion and to reduce the infarction zone by 50% without any adverse effect. All compounds exhibit a moderate or small toxicity and are active in low doses. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00075-4

文献信息

• The chemistry of naphthazarin derivatives
  作者：A. Ya. Chizhova、T. Yu. Kochergina、V. F. Anufriev、V. A. Denisenko、V. P. Glazunov

  DOI：10.1007/bf02494641

  日期：1999.5

  The 7,7′-dideoxy analog of islandoquinone, binaphthazarin of a new structural type, bearing a 2-oxo-2,3-dihydro-1,4-naphthoquinone moiety was synthesized. The carbonyl group at the C(2) atom of this binaphthazarin easily adds water to give the correspondinggem-diol. Comparison of the spectral characteristics of the prepared diol and islandoquinone made it possible to elucidate more precisely the structure

  合成了带有 2-oxo-2,3-dihydro-1,4-naphthoquinone 部分的新结构类型的海岛醌的 7,7'-双脱氧类似物，binaphthazarin。该联萘甲素的 C(2) 原子上的羰基很容易加水得到相应的宝石二醇。比较制备的二醇和岛醌的光谱特性，可以更精确地阐明后者的结构。
• Chemistry of naphthazarin derivatives. 11. Trisubstituted hydroquinone derivatives in the preparative synthesis of naphthazarins
  作者：V. Ph. Anufriev、S. G. Polonik、N. D. Pokhilo、N. N. Balanyova

  DOI：10.1023/b:rucb.0000011886.03785.bd

  日期：2003.10

  5-diethyl-2-hydroxyhydroquinone, and 3,5-diethyl-1,2,4-trimethoxybenzene with dichloromaleic or citraconic anhydride in an AlCl3—NaCl melt is accompanied by o-C-dealkylation to afford functionally substituted naphthazarins.

  三甲基氢醌、3,5-二乙基-2-羟基氢醌和 3,5-二乙基-1,2,4-三甲氧基苯与二氯马来酸酐或柠康酸酐在 AlCl3-NaCl 熔体中的 Friedel-Crafts 酰化伴随 oC-脱烷基化为提供功能性取代的萘萨林。
• Synthesis and study on oxidative coupling products of 3-alkyl-2-hydroxynaphthazarins
  作者：D. N. Pelageev、S. V. Dragan、M. A. Pushilin、V. A. Denisenko、D. V. Berdishev、V. P. Glasunov、V. Ph. Anufriev

  DOI：10.1007/s11172-012-0294-0

  日期：2012.11

  The resulting products of oxidative coupling of substituted 3-alkyl-2-hydroxynaphthazarins in the presence of lead dioxide are the compounds with 7,14-dibenzo[a,i]oxanthrene skeleton.

  在二氧化铅存在下，取代的 3-烷基-2-羟基萘杂蒽氧化偶联的产物是以 7,14- 二苯并[a,i]氧杂蒽为骨架的化合物。
• Effect of 5-hydroxy- and 5,8-dihydroxy-1,4-naphthoquinones on the hydrolytic activity of α-galactosidase
  作者：I. Yu. Bakunina、E. A. Kol′tsova、N. D. Pokhilo、O. P. Shestak、A. Ya. Yakubovskaya、T. N. Zvyagintseva、V. F. Anufriev

  DOI：10.1007/s10600-009-9252-y

  日期：2009.1

  The effect of natural and synthetic polyhydroxy-1,4-naphthoquinones on the hydrolytic activity of α-galactosidase from marine bacteria was studied. It was shown that the inhibiting properties relative to the enzyme depended on the nature of the substituents, their number, and their position in the structure of these compounds.

  研究了天然和合成多羟基-1,4-萘醌对海洋细菌中 α-半乳糖苷酶水解活性的影响。结果表明，对酶的抑制特性取决于取代基的性质、数量以及在这些化合物结构中的位置。
• Synthesis of (+/–)-Mesocentroquinone, a Biquinone of a Novel Structural Class and Metabolite of Sea Urchins Mesocentrotus nudus and Strongylocentrotus intermedius, and Related Compounds#
  作者：K. L. Borisova、D. N. Pelageev、G. I. Mel’man、B. P. Mashnev、V. F. Anufriev

  DOI：10.1007/s10600-022-03855-y

  日期：2022.11

  The synthesis of mesocentroquinone, a metabolite of the sea urchins Mesocentrotus nudus and Strongylocentrotus intermedius, is described. The procedure includes bromination of 2-hydroxy-6,7-dimethoxy-3-ethylnaphthazarin, dehydrobromination of the resulting 1′-bromoethyl derivative, and heterodiene condensation of the 2-oxo-3-ethylidene- and 3-vinyl-2-hydroxy-derivatives formed by this. The general nature of the proposed approach to the synthesis of 2-(1,4-naphthoquinon-2-yl)-benzo[g]-2Hbenzochromene-5,10-diones is demonstrated using two examples.

  本文描述了介中醌（一种海胆Mesocentrotus nudus和Strongylocentrotus intermedius的代谢产物）的合成。该过程包括2-羟基-6,7-二甲氧基-3-乙基萘嗪的溴化、所得1′-溴乙基衍生物的脱溴以及由此形成的2-氧代-3-亚乙基-和3-乙烯基-2-羟基衍生物的杂二烯缩合。本文通过两个例子证明了所提出的2-(1,4-萘醌-2-基)-苯并[g]-2H苯并吡喃-5,10-二酮合成方法的一般性质。