1,4-naphthalenediol | 571-59-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,4-naphthalenediol
• 英文别名: naphthohydroquinone；1,4-Naphthalenediol, 1,4-dihydro-；1,4-dihydronaphthalene-1,4-diol
• CAS: 571-59-5
• 化学式: C₁₀H₁₀O₂
• 分子量: 162.188
• InChiKey: QRZINIDQKGUJSY-UHFFFAOYSA-N

物化性质

• 熔点：
  211-212 °C
• 沸点：
  364.9±30.0 °C(Predicted)
• 密度：
  1.312±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,4-naphthalenediol 在 甲酸 、 5%-palladium/activated carbon 、 氢气 、 维生素 C 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 nordihydrolapachenol
  参考文献：
  名称：

  取代苯并[h]色原醇的合成及自由基清除活性

  摘要：

  Benzo[h]chromanols, which possess a tocopherol moiety, have been reported to exhibit potent antioxidant activity. Several benzo[h]chromanols with various substituents (nitro, chloro, bromo, methyl, or amino groups at the position ortho to the phenolic OH group) were synthesized, and the second-order rate constants (k) of their reaction with the galvinoxyl radical were determined. The introduction of electron-withdrawing bromo, chloro and nitro groups decreased the activity, and the activity correlated well with the substituent effect. ortho-Aminobenzo[h]chromanol showed the highest radical scavenging activity among the compounds synthesized.

  DOI：

  10.3987/com-17-13671
• 作为产物：
  描述：

  1,4-萘醌 在 potassium phosphate buffer 、 pig testicular 20β-hydroxysteroid dehydrogenase 、 还原型辅酶II(NADPH)四钠盐 作用下， 生成 1,4-naphthalenediol
  参考文献：
  名称：

  Carbonyl Reductase Activity Exhibited by Pig Testicular 20.BETA.-Hydroxysteroid Dehydrogenase.

  摘要：

  利用重组酶检测了猪睾丸20β-羟基类固醇脱氢酶(20β-HSD)表现出的羰基还原酶活性。获得了包括芳香醛、芳香酮、环酮、醌、脂肪醛和脂肪酮在内的48种含羰基基团底物的动力学参数。20β-HSD对醌类如9,10-菲醌、α-萘醌和维生素K3表现出高亲和性(Km值分别为4、2和5 μM)，且该酶对这些醌的底物利用效率(Vmax/Km)非常高。环己酮和2-甲基环己酮也以高Vmax/Km值被还原，但环戊酮和2-甲基环戊酮未被还原。各种芳香醛和酮类包括苯甲醛和苯乙酮的衍生物均被20β-HSD还原。尤其是，4-硝基苯甲醛和4-硝基苯乙酮在相关化合物中以高Vmax/Km值被还原。该酶也还原吡啶衍生物，2-、3-和4-苯甲酰吡啶，其中2-苯甲酰吡啶的Vmax/Km值最高。20β-HSD还原脂肪醛和脂肪酮，但对前者的还原效率更高。讨论了羰基化合物的结构和其底物Vmax/Km之间的相关性。

  DOI：

  10.1248/bpb.20.1215

文献信息

• Rabbit 3-hydroxyhexobarbital dehydrogenase is a NADPH-preferring reductase with broad substrate specificity for ketosteroids, prostaglandin D2, and other endogenous and xenobiotic carbonyl compounds
  作者：Satoshi Endo、Toshiyuki Matsunaga、Atsuko Matsumoto、Yuki Arai、Satoshi Ohno、Ossama El-Kabbani、Kazuo Tajima、Yasuo Bunai、Shigeru Yamano、Akira Hara、Yukio Kitade

  DOI：10.1016/j.bcp.2013.08.024

  日期：2013.11

  for NADP(H) over NAD(H) at a physiological pH of 7.4. In the NADPH-linked reduction, 3HBD showed broad substrate specificity for a variety of quinones, ketones and aldehydes, including 3-, 17- and 20-ketosteroids and prostaglandin D(2), which were converted to 3alpha-, 17beta- and 20alpha-hydroxysteroids and 9alpha,11beta-prostaglandin F(2), respectively. Especially, alpha-diketones (such as isatin

  3-羟基己异巴比妥脱氢酶（3HBD）催化将NAD（P）（+）链接的3-羟基己异巴比妥氧化为3-羟基己异巴比妥。该酶被认为是异生物醇和某些羟基类固醇的脱氢酶，但其生理功能仍然未知。我们已经纯化了兔3HBD，分离了其cDNA，并检查了其对辅酶和底物的特异性，反应方向性和组织分布。3HBD是醛酮还原酶（AKR）超家族的成员（AKR1C29），并且在7.4的生理pH值下，NADP（H）优于NAD（H）。在与NADPH相关的还原反应中，3HBD对多种醌，酮和醛（包括3-，17-和20-酮类固醇和前列腺素D（2））显示出广泛的底物特异性，它们被转化为3alpha-，17beta-和20alpha -羟基类固醇和9alpha，11beta-前列腺素F（2），分别。特别是，α-二酮（如isatin和diacetyl）和脂质过氧化衍生的醛（如4-oxo-和4-hydroxy-2-nonenals）是显示低K（m）值（0
• METHOD FOR PREPARING ORTHO-SUBSTITUTED AMINOFERROCENES
  申请人：Metallinos Costa

  公开号：US20100137588A1

  公开（公告）日：2010-06-03

  The present disclosure relates to a method for preparing an ortho-substituted aminoferrocene comprising reacting an aminoferrocene with a Lewis acid and a lithiating reagent in the presence of an electrophile to form the ortho-substituted aminoferrocene.

  本公开涉及一种制备邻位取代氨基二茂铁的方法，包括将氨基二茂铁与路易斯酸和锂试剂在电泳性物质存在下反应，形成邻位取代氨基二茂铁。
• Methods For Preparing Fluoroalkyl Arylsulfinyl Compounds And Fluorinated Compounds Thereto
  申请人：Umemoto Teruo

  公开号：US20110190511A1

  公开（公告）日：2011-08-04

  Novel preparative methods for fluoroalkyl arylsulfinyl compounds are disclosed. Fluorinated compounds as useful fluorinated compounds, intermediates, or builing blocks are disclosed. Useful applications of the fluoroalkyl arylsulfinyl compounds are shown.

  本发明揭示了一种用于制备氟烷基芳基亚磺酰化合物的新型制备方法。本发明还揭示了氟化合物作为有用的氟化合物、中间体或构建块。同时，本发明还展示了氟烷基芳基亚磺酰化合物的有用应用。
• Methods for Preparing Fluoroalkyl Arylsulfinyl Compounds and Fluorinated Compounds Thereto
  申请人：Umemoto Teruo

  公开号：US20100152463A1

  公开（公告）日：2010-06-17

  Novel preparative methods for fluoroalkyl arylsulfinyl compounds are disclosed. Fluorinated compounds as useful fluorinated compounds, intermediates, or building blocks are disclosed. Useful applications of the fluoroalkyl arylsulfinyl compounds are shown.

  本发明公开了用于制备氟烷基芳基磺酰基化合物的新型制备方法。本发明还公开了作为有用的氟化合物、中间体或构建块的氟化合物。本发明还展示了氟烷基芳基磺酰基化合物的有用应用。
• Mechanistic and Crystallographic Studies of Azoreductase AzoA from <i>Bacillus wakoensis</i> A01
  作者：Elvira Romero、Simone Savino、Marco W. Fraaije、Nikola Lončar

  DOI：10.1021/acschembio.9b00970

  日期：2020.2.21

  The azoreductase AzoA from the alkali-tolerant Bacillus wakoensis A01 has been studied to reveal its structural and mechanistic details. For this, a recombinant expression system was developed which yields impressive amounts of fully active enzyme. The purified holo enzyme is remarkably solvent-tolerant and thermostable with an apparent melting temperature of 71 degrees C. The dimeric enzyme contains FMN as a prosthetic group and is strictly NADH dependent. While AzoA shows a negligible ability to use molecular oxygen as an electron acceptor, it is efficient in reducing various azo dyes and quinones. The kinetic and catalytic mechanism has been studied in detail using steady state kinetic analyses and stopped-flow studies. The data show that AzoA performs quinone and azo dye reductions via a two-electron transfer. Moreover, quinones were shown to be much better substrates (k(cat )values of 100-400 s(-1) for several naphtoquinones) when compared with azo dyes. This suggests that the physiological role of AzoA and sequence-related microbial reductases is linked to quinone reductions and that they can better be annotated as quinone reductases. The structure of AzoA has been determined in complex with FMN at 1.8 angstrom resolution. AzoA displays unique features in the active site providing clues for explaining its catalytic and thermostability features. An uncommon loop, when compared with sequence-related reductases, forms an active site lid with Trp60 acting as an anchor. Several Trp60 mutants have been analyzed disclosing an important role of this residue in the stability of AzoA, while they retained activity. Structural details are discussed in relation to other azo and quinone reductases. This study provides new insights into the molecular functioning of AzoA and sequence-related reductases.