2,5,8-trihydroxy-3-methyl-6,7-dichloro-1,4-naphthoquinone | 187149-19-5

• 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-3-methyl-6,7-dichloro-1,4-naphthoquinone
• 英文别名: 6,7-dichloro-2,5,8-trihydroxy-3-methyl-1,4-naphthoquinone
• CAS: 187149-19-5
• 化学式: C₁₁H₆Cl₂O₅
• 分子量: 289.072
• InChiKey: LGTPFUFUFYEBOC-UHFFFAOYSA-N

物化性质

• 沸点：
  566.7±50.0 °C(Predicted)
• 密度：
  1.849±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  18.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 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-3-methyl-6,7-dichloro-1,4-naphthoquinone 在 一氧化二氯 作用下， 以 四氯化碳 为溶剂， 生成 3,6,7-trichloro-5,8-dihydroxy-3-methyl-2-oxo-2,3-dihydro-1,4-naphthoquinone
  参考文献：
  名称：

  萘甲素衍生物的化学性质

  摘要：

  在含水有机溶剂中，2-氧代-2,3-二氢萘醌衍生物水合得到相应的2,2-二羟基-2,3-二氢萘醌。水合作用是可逆的；在某些情况下，建立了酮-宝石-二醇平衡。2-oxo-2,3-dihydronaphthoquinone 衍生物对水合的敏感性取决于 C(3)、C(6) 和 C(7) 处取代基的供体-受体性质，以及羟基是否存在于C(5)和C(8)，以及关于有机溶剂的碱度。

  DOI：

  10.1007/bf02494776
• 作为产物：
  描述：

  2,3-二氯马来酸酐 、 2,3,6-trimethoxytoluene 在 三氯化铝 、 sodium chloride 作用下， 反应 0.08h， 以65%的产率得到2,5,8-trihydroxy-3-methyl-6,7-dichloro-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

• Synthesis of Spinochrome D, A Metabolite of Various Sea-Urchin Species
  作者：N. N. Balaneva、O. P. Shestak、V. F. Anufriev、V. L. Novikov

  DOI：10.1007/s10600-016-1597-4

  日期：2016.3

  The sea-urchin metabolite spinochrome D (1) was synthesized in 58% overall yield via oxidation of 2,3-dichloronaphthazarin (13) into 2-hydroxy-6,7-dichloronaphthazarin (14), O-methylation of 14, nucleophilic substitution by MeO groups of the Cl atoms in the resulting 2-methoxy-6,7-dichloronaphthazarin (19), and hydrolysis of the obtained 2,3,6-trimethoxynaphthazarin (10).

  通过将 2,3-二氯萘扎林 (13) 氧化成 2-羟基-6,7-二氯萘扎林 (14)、14 的 O-甲基化、亲核取代，以 58% 的总产率合成了海胆代谢物棘色素 D (1)通过生成的 2-甲氧基-6,7-二氯萘扎林 (19) 中的 Cl 原子的 MeO 基团，水解得到的 2,3,6-三甲氧基萘扎林 (10)。
• Selective Chlorination of Hydroxynaphthazarins with Dichlorine Monoxide. Remarkable Stability of some Geminal Diols Derived from 2,3-Dihydro-2-oxonaphthazarin
  作者：Alla Ya. Tchizhova、Victor Ph. Anufriev、Valery P. Glazunov、Vladimir A. Denisenko、Olga P. Moiseenko

  DOI：10.1080/00397919908085917

  日期：1999.11

  Abstract The ration of 2-hydroxynaphthazarins with dichlorine monoxide in CC14 affords the stable gem-diols - 3,3-dichloro-2,3-dihydro-2,2-dihydroxy-paphthazarins in quantitative yields. In the case of 2-hydroxy-3-methyl-iiaphthazarins the formation of the mixture of corresponding monochlorinated at 3 position 2,3-dihydro-3-methyl-2-oxonaphthazarins and 2,3-dihydro-3-methyl-2,2-dihydroxynaphthazarins

  摘要 在 CC14 中，2-羟基萘甲素与一氧化二氯的配比以定量收率提供了稳定的 gem-二醇 - 3,3-二氯-2,3-二氢-2,2-二羟基-萘甲素。在 2-羟基-3-甲基-噻吩噻唑啉的情况下，形成相应的在 3 位单氯化的 2,3-二氢-3-甲基-2-氧萘扎林和 2,3-二氢-3-甲基-2 的混合物，发生 2-二羟基萘萨林。对于这些化合物，在某些条件下，观察到酮-偕二醇平衡。
• A Convenient Method for the Selective Alkylation ofβ-OH Groups of 2(3)-Hydroxyjuglones and Hydroxynaphthazarines
  作者：Victor Ph.Anufriev、Vyacheslav L. Novikov、Galina V. Malinovskaya、Valery P. Glazunov

  DOI：10.1080/00397919708004812

  日期：1997.1.1
• Synthesis of water-soluble N-Acetyl-L-cysteine conjugates of naphtazarin (5,8-Dihydroxy-1,4-naphthoquinone) derivatives
  作者：Yu. E. Sabutskii、N. S. Polonik、V. A. Denisenko、P. S. Dmitrenok、S. G. Polonik

  DOI：10.1134/s1070428013080101

  日期：2013.8

  Base-catalytic condensation of N-acetyl-L-cysteine with substituted naphthazarins was first obtained a series of mono-, di-, tri- and tetra-substituted S-aminoacid naphthazarin conjugates bearing alkyl (hydroxy) groups. It was shown that three- and tetra-N-acetyl-L-cysteine naphthazarin derivatives are readily soluble in water.
• Synthesis and properties of water-soluble 5,8-dihydroxy-1,4-naphthoquinone thioglucosides structurally related to echinochrome
  作者：S. G. Polonik

  DOI：10.1134/s1070428009100091

  日期：2009.10

  Acetylated hydroxynaphthazarin di- and trithioglucosides structurally related to echinochrome were synthesized. Their deacetylation by the action of sodium methoxide in methanol and the effect of hydroxy groups on this process were studied. Water-soluble echinochrome thioglucosides were synthesized for the first time.