3,6-diethyl-2,7-dihydroxynaphthazarin | 367922-84-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3,6-diethyl-2,7-dihydroxynaphthazarin
• 英文别名: 2,5,7,8-tetrahydroxy-3,6-diethyl-1,4-naphthoquinone；3,6-diethyl-2,5,7,8-tetrahydroxy-1,4-naphthoquinone
• CAS: 367922-84-7
• 化学式: C₁₄H₁₄O₆
• 分子量: 278.262
• InChiKey: HBNDOLPTCUJEGY-UHFFFAOYSA-N

物化性质

• 沸点：
  553.0±50.0 °C(Predicted)
• 密度：
  1.535±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.97
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  115.06
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 3,6-diethyl-2,7-dihydroxynaphthazarin 以 乙醚 为溶剂， 以36%的产率得到3,6-diethyl-2,5,8-trihydroxy-7-methoxy-1,4-naphthoquinone
  参考文献：
  名称：

  First direct observation of tautomerism of monohydroxynaphthazarins by IR-spectroscopy

  摘要：

  Some substituted monohydroxylated naphthazarins (5,8-dihydroxy-1,4-naphthoquinones) were synthesized and studied by IR-spectroscopy in aprotic organic solvents at ambient temperature. Two narrow stretching mode bands in the high frequency range 3540-3410 cm(-1) due to a beta-hydroxy group were observed; it was established that this effect was caused by tautomerism. This allowed the creation of a convenient and accurate method for the measurement of a small amount of tautomer engaged in rapid exchange with the principal tautomer. Solvent and substituent effects were estimated. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00060-1
• 作为产物：
  描述：

  过氧化(二)丙酰 、 4,5,7,8-四羟基萘-1,2-二酮 以 叔丁醇 为溶剂， 以51%的产率得到6-ethyl-4,5,7,8-tetrahydroxynaphthalene-1,2-dione
  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

• 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。
• ——
  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.
• First direct observation of tautomerism of monohydroxynaphthazarins by IR-spectroscopy
  作者：Valery P. Glazunov、Alla Ya. Tchizhova、Nataly D. Pokhilo、Victor Ph. Anufriev、George B. Elyakov

  DOI：10.1016/s0040-4020(02)00060-1

  日期：2002.2

  Some substituted monohydroxylated naphthazarins (5,8-dihydroxy-1,4-naphthoquinones) were synthesized and studied by IR-spectroscopy in aprotic organic solvents at ambient temperature. Two narrow stretching mode bands in the high frequency range 3540-3410 cm(-1) due to a beta-hydroxy group were observed; it was established that this effect was caused by tautomerism. This allowed the creation of a convenient and accurate method for the measurement of a small amount of tautomer engaged in rapid exchange with the principal tautomer. Solvent and substituent effects were estimated. (C) 2002 Elsevier Science Ltd. All rights reserved.
• ——
  作者：V. P. Glazunov、A. Ya. Tchizhova、M. I. Shuvalova、V. Ph. Anufriev

  DOI：10.1023/a:1009581319518

  日期：——

  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.