6-chloro-5,8-dihydroxy-2,7-dimethoxy-1,4-naphthoquinone | 367922-92-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-chloro-5,8-dihydroxy-2,7-dimethoxy-1,4-naphthoquinone
• 英文别名: 5,8-dihydroxy-2,7-dimethoxy-6-chloro-1,4-naphthoquinone；6-chloro-5,8-dihydroxy-2,7-dimethoxynaphthalene-1,4-dione
• CAS: 367922-92-7
• 化学式: C₁₂H₉ClO₆
• 分子量: 284.653
• InChiKey: DVWOCGRZKCOHEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-chloro-5,8-dihydroxy-2,7-dimethoxy-1,4-naphthoquinone 在 氢溴酸 作用下， 以 叔丁醇 为溶剂， 反应 0.25h， 生成 6-chloro-3-ethyl-2,5,7,8-tetrahydroxy-1,4-naphthoquinone
  参考文献：
  名称：

  摘要：

  A set of substituted 2,6- and 2,7-dihydroxynaphthazarins were synthesized. The difference in the UV spectra of alkaline alcoholic solutions of 2,6- and 2,7-dihydroxynaphthazarins allows the reliable differentiation of the structures of these compounds. The IR spectra of 2,6- and 2,7-dihydroxynaphthazarins have characteristic nonoverlapping intervals of stretching vibration frequencies of the beta -hydroxy groups. Based on these spectral regularities, the data on cuculoquinone, which has been isolated previously from lichen Cetraria cucullata and has been identified as 7,7'-bis(3-ethyl-2,5,6,8-tetrahydroxynaphthalene-1,4-dione), were revised and the structure of 6,6 '-bis(3-ethyl-2,5,7,8-tetrahydroxynaphthalene- 1,4-dione) was assigned to this compound.

  DOI：

  10.1023/a:1009581319518
• 作为产物：
  描述：

  2,3-dichloro-5,8-dihydroxy-[1,4]naphthoquinone 在 manganese(IV) oxide 、 aluminum oxide 、 硫酸 、 cesium fluoride 作用下， 以 乙醚 为溶剂， 反应 10.0h， 生成 6-chloro-5,8-dihydroxy-2,7-dimethoxy-1,4-naphthoquinone
  参考文献：
  名称：

  摘要：

  A set of substituted 2,6- and 2,7-dihydroxynaphthazarins were synthesized. The difference in the UV spectra of alkaline alcoholic solutions of 2,6- and 2,7-dihydroxynaphthazarins allows the reliable differentiation of the structures of these compounds. The IR spectra of 2,6- and 2,7-dihydroxynaphthazarins have characteristic nonoverlapping intervals of stretching vibration frequencies of the beta -hydroxy groups. Based on these spectral regularities, the data on cuculoquinone, which has been isolated previously from lichen Cetraria cucullata and has been identified as 7,7'-bis(3-ethyl-2,5,6,8-tetrahydroxynaphthalene-1,4-dione), were revised and the structure of 6,6 '-bis(3-ethyl-2,5,7,8-tetrahydroxynaphthalene- 1,4-dione) was assigned to this compound.

  DOI：

  10.1023/a:1009581319518

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)。
• ——
  作者：V. P. Glazunov、A. Ya. Tchizhova、O. P. Shestak、G. I. Sopel"nyak、V. Ph. Anufriev

  DOI：10.1023/a:1009533403588

  日期：——

  A set of substituted 2-hydroxy-6(7)-methoxynaphthazarins and 7(8)-hydroxypyranonaphthazarins were synthesized. The IR spectra of 2-hydroxy-6-methoxynaphthazarins and 7-hydroxypyranonaphthazarins, on the one hand, and of 2-hydroxy-7-methoxynaphthazarins and 8-hydroxypyranonaphthazarins, on the other hand, have the characteristic nonoverlapping intervals of stretching vibration frequencies of the beta -hydroxy groups. These regularities confirm the structures of cristazarin and 6-methylcristazarin, which are metabolites of lichen Cladonia cristatella.