5,8-Dihydroxy-2,3-dichloro-6-ethyl-7-ethoxy-1,4-naphthoquinone | 168140-17-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5,8-Dihydroxy-2,3-dichloro-6-ethyl-7-ethoxy-1,4-naphthoquinone
• 英文别名: 1,4-Naphthalenedione, 2,3-dichloro-6-ethoxy-7-ethyl-5,8-dihydroxy-；2,3-dichloro-6-ethoxy-7-ethyl-5,8-dihydroxynaphthalene-1,4-dione
• CAS: 168140-17-8
• 化学式: C₁₄H₁₂Cl₂O₅
• 分子量: 331.152
• InChiKey: UXMJRBIDNCCMTB-UHFFFAOYSA-N

物化性质

• 沸点：
  550.3±50.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,8-Dihydroxy-2,3-dichloro-6-ethyl-7-ethoxy-1,4-naphthoquinone 在 sodium dithionite 、 水 、 sodium nitrite 作用下， 以 甲醇 、 乙酸乙酯 、 丙酮 为溶剂， 反应 6.0h， 生成 3-amino-7-ethyl-2,5,6,8-tetrahydroxy-1,4-dihydronaphthlene-1,4-dione
  参考文献：
  名称：

  Reaction of Dichloronaphthazarins with Sodium Nitrite as a Route to Natural Pigments Echinamines A and B and Related Aminonaphthazarins

  摘要：

  一系列6,7-取代的2-羟基-3-硝基萘唑被制备，方法是将2,3-二氯萘唑与亚硝酸钠反应。通过酸催化水解一混合的两个异构体6(7)-乙氧基-7(6)-乙基取代的2-羟基-3-硝基萘唑，随后进行色谱分离，得到了引物独立的艾奇胺A和B。进一步使用各种还原剂对硝基喹酮进行还原，良好产率地得到了艾奇胺及相关的3-氨基-2-羟基萘唑。

  DOI：

  10.1055/s-0030-1260229

文献信息

• Fluoride salts-alcohols-alumina as reagents for nucleophilic substitution of chlorine atoms for alkoxy groups in 2,3-dichlorosubstituted juglones, naphthazarines, and quinizarines
  作者：Victor Ph. Anufriev、Vyacheslav L. Novikov

  DOI：10.1016/0040-4039(95)00295-n

  日期：1995.4

  Direct displacement of chlorine atoms by alkoxy groups in 2,3-dichlorosubstituted juglones (5-hydroxy-1,4-naphthoquinones), naphthazarines (5,8-dihydroxy-1,4-naphthoquinones), and quinizarines (1,4-dihydroxy-9,10-anthraquinones) is generally ineffective, however high yields are obtained when methanol or cellosolves activated by fluoride anion are used as nucleophiles and the reaction goes in the presence

  2,3-二氯取代的聚对二甲苯（5-羟基-1,4-萘醌），萘萘烷（5,8-二羟基-1,4-萘醌）和喹唑啉（1,4-二羟基）中的烷氧基直接取代氯原子（-9，10-蒽醌）通常无效，但是当将甲醇或由氟阴离子活化的溶纤剂用作亲核试剂并且反应在氧化铝的存在下进行时，可获得高产率。
• Conversion of 2,3-dihydroxynaphthazarins to isoquinoline-1,3,4(2H)-trione derivatives
  作者：K. L. Borisova、G. I. Mel’man、V. A. Denisenko、V. P. Glazunov、V. F. Anufriev

  DOI：10.1007/s11172-012-0089-3

  日期：2012.3

  6(7)-(Di)alkyl- and 6(7)-(di)alkoxy derivatives of 2,3-dihydroxynaphthazarin were converted to 5,8-dihydroxyisoquinoline-1,3,4(2H)-trione derivatives under amination reaction conditions.

  在胺化反应条件下，2,3-二羟基萘甲萘醌的 6(7)-(二)烷基和 6(7)-(二)烷氧基衍生物被转化为 5,8-二羟基异喹啉-1,3,4(2H)-三酮衍生物。
• Catalytic activity of sorbents containing metals, and nucleophilicity of alcohols activated with fluoride anion in reaction of nucleophilic substitution in 2,3-dichloronaphthazarines
  作者：G. V. Malinovskaya、V. F. Anufriev、V. P. Glazunov

  DOI：10.1007/bf02757441

  日期：2000.6

  In reaction of 5,8-dihydroxy-2,3-dichloro-6-ethyl-7-ethoxy-1,4-naphthoquinone and 6-tert-butyl-5,8-dihydroxy-2,3-dichloro-1,4-naphthoquinone proceeding on the surface of molecular sieves, calcium phosphate and carbonate, neutral alumina, or magnesium silicate with nucleophilic reagents (methanol, 2-methoxyethanol, monomethyl ethers of di- and triethylene glycols) activated with fluoride anion the yield of products decreased in this nucleophiles series. The most active catalysts among sorbents are alumina and magnesium silicate. All the sorbents are also efficient catalysts of alkoxy groups interchange.
• ——
  作者：T. Yu. Kochergina、V. F. Anufriev

  DOI：10.1023/a:1016551223482

  日期：——

  The nucleophilic substitution of halogen by methoxy groups in 5,8-dihydroxy-2,3-dichloro-1,4-naphthoquinones effected by complex reagent KF-MeOH-Al2O3 is considerably accelerated in the presence of electron-donor solvents.
• Reaction of Dichloronaphthazarins with Sodium Nitrite as a Route to Natural Pigments Echinamines A and B and Related Aminonaphthazarins
  作者：Nikita Polonik、Sergey Polonik、Vladimir Denisenko、Olga Moiseenko

  DOI：10.1055/s-0030-1260229

  日期：2011.10

  A series of 6,7-disubstituted 2-hydroxy-3-nitronaphthazarins were prepared by treatment of 2,3-dichloronaphthazarins with sodium nitrite. Acid-catalyzed hydrolysis of a mixture of two isomeric 6(7)-ethoxy-7(6)-ethyl-substituted 2-hydroxy-3-nitronaph­thazarins followed by chromatographic separation led to the individually precursors of echinamines A and B. Further reduction of nitroquinones using various reducing agents gave echinamines and related 3-amino-2-hydroxynaphthazarins in good yields.

  一系列6,7-取代的2-羟基-3-硝基萘唑被制备，方法是将2,3-二氯萘唑与亚硝酸钠反应。通过酸催化水解一混合的两个异构体6(7)-乙氧基-7(6)-乙基取代的2-羟基-3-硝基萘唑，随后进行色谱分离，得到了引物独立的艾奇胺A和B。进一步使用各种还原剂对硝基喹酮进行还原，良好产率地得到了艾奇胺及相关的3-氨基-2-羟基萘唑。