3-ethyl-2-hydroxy-7-methoxynaphthazarin | 15254-99-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-ethyl-2-hydroxy-7-methoxynaphthazarin
• 英文别名: 2,5,8-trihydroxy-7-methoxy-3-ethyl-1,4-naphthaquinone；2,5,8-trihydroxy-7-methoxy-3-ethyl-1,4-naphthoquinone；3-ethyl-2,5,8-trihydroxy-7-methoxy-1,4-naphthoquinone；cristazarin；crystazarin；3-Aethyl-2-hydroxy-7-methoxy-naphthazarin
• CAS: 15254-99-6
• 化学式: C₁₃H₁₂O₆
• 分子量: 264.235
• InChiKey: HTNKGHXSGYCDDM-UHFFFAOYSA-N

物化性质

• 熔点：
  228-230 °C
• 沸点：
  578.4±50.0 °C(Predicted)
• 密度：
  1.518±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.71
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  104.06
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3-ethyl-2-hydroxy-7-methoxynaphthazarin 在 溴 作用下， 以 四氯化碳 为溶剂， 以69 %的产率得到2-(1-bromoethyl)-3,5,8-trihydroxy-6-methoxynaphthalene-1,4-dione
  参考文献：
  名称：

  Synthesis of (+/–)-Mesocentroquinone, a Biquinone of a Novel Structural Class and Metabolite of Sea Urchins Mesocentrotus nudus and Strongylocentrotus intermedius, and Related Compounds#

  摘要：

  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。

  DOI：

  10.1007/s10600-022-03855-y
• 作为产物：
  描述：

  重氮甲烷 、 6-ethyl-4,5,7,8-tetrahydroxynaphthalene-1,2-dione 以 乙醚 为溶剂， 以68%的产率得到3-ethyl-2-hydroxy-7-methoxynaphthazarin
  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

文献信息

• Reaction of 6-hydroxy-2,3-dichloro-7-ethylnaphthazarin with KF—MeOH—AL2O3. synthesis of cristazarin, a metabolite of the lichen Cladonia cristatella
  作者：T. Yu. Kochergina、V. F. Anufriev

  DOI：10.1007/s10600-011-9819-2

  日期：2011.3

  The reaction of 2-hydroxy-6-methoxy-7-chloro-3-ethylnaphthazarin with methanol activated by fluoride anion on the surface of Al2O3 at 120°C gave echinochrome dimethyl ether, a metabolite of the sea urchin Scaphechinus mirabilis. Its isomer 2-hydroxy-7-methoxy-6-chloro-3-ethylnaphthazarin was converted under the same conditions into cristazarin, a metabolite of the lichen Cladonia cristatella.

  在120°C下，2-羟基-6-甲氧基-7-氯-3-乙基萘嗪与甲醇在Al2O3表面与氟离子发生反应，生成海胆Scaphechinus mirabilis的代谢产物棘皮色素二甲醚。其异构体2-羟基-7-甲氧基-6-氯-3-乙基萘嗪在相同条件下转化为地衣Cladonia cristatella的代谢产物cristazarin。
• ——
  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.
• 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。