2,3-二羥蒽醌 | 483-35-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 2,3-二羥蒽醌
• 英文名称: hystazarin
• 英文别名: 2,3-dihydroxy-9,10-anthraquinone；2,3-Dihydroxyanthracene-9,10-dione
• CAS: 483-35-2
• 化学式: C₁₄H₈O₄
• 分子量: 240.215
• InChiKey: KQSBZNJFKWOQQK-UHFFFAOYSA-N

物化性质

• 熔点：
  260-262 °C
• 沸点：
  424.9±40.0 °C(Predicted)
• 密度：
  1.540±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3-二羥蒽醌 在 sodium tetrahydroborate 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 生成 2,3-bis-n-decyloxyanthracene
  参考文献：
  名称：

  A novel small molecular luminescent gelling agent for alcohols

  摘要：

  2,3-双正癸氧基蒽在极低浓度下就能与醇类形成热可逆凝胶；电子吸收光谱和荧光发射研究表明，凝胶网络由与醇类共存的芳香族成分的头尾集合体组成，系统的组织主要依靠偶极力和范德华相互作用。

  DOI：

  10.1039/c39910000416
• 作为产物：
  描述：

  2-(3,4-二甲氧基苯甲酰基)苯甲酸 在 硫酸 作用下， 生成 2,3-二羥蒽醌
  参考文献：
  名称：

  Lagodzinski, Chemische Berichte, 1895, vol. 28, p. 118

  摘要：

  DOI：

文献信息

• STABILIZATION OF HYDROXYLAMINE CONTAINING SOLUTIONS AND METHOD FOR THEIR PREPARATION
  申请人：Lee Wai Mun

  公开号：US20090112024A1

  公开（公告）日：2009-04-30

  The invention relates to the use of amidoximes for prevention of or stabilization of hydroxylamine compounds against undesired decomposition.

  本发明涉及将酰胺肟用于预防或稳定羟基胺化合物，防止其不受控分解。
• 2,3-Di-n-alkoxyanthraquinones as gelators of organic solvents
  作者：Gilles Michel Clavier、Jean-François Brugger、Henri Bouas-Laurent、Jean-Luc Pozzo

  DOI：10.1039/a803302a

  日期：——

  The gelling ability of a series of dialkoxy-9,10-anthraquinone derivatives has been investigated in a number of organic solvents at different concentrations. The most efficient systems were found to be formed from the 2,3-dialkoxy (OCnH2n + 1) derivatives with n = 8–11 (compounds 9–11, 14–15). In ethanol, a gel is formed with 2,3-di-n-decyloxyanthraquinone (11) at a concentration of ca. 10–2M (0.65 g/100 g) at 30 °C. The gel-to-sol transition temperatures were determined in ethanol, isopropanol and n-heptane as a function of gelling agent concentration. The gel-to-sol transition enthalpies (23–51 kJ mol–1) were found to be in agreement with recent results obtained for other gel forming systems.

  一系列二烷氧基-9,10-蒽醌衍生物在不同浓度的有机溶剂中进行了凝胶能力的研究。最有效的体系是由2,3-二烷氧基（OCnH2n + 1）衍生物形成的，其中n = 8–11（化合物9–11, 14–15）。在乙醇中，2,3-二-n-十二烷氧基蒽醌（11）在约10–2M的浓度（0.65 g/100 g）下于30°C形成凝胶。研究了醇-凝胶转变温度在乙醇、异丙醇和正庚烷中作为凝胶剂浓度的函数。发现凝胶-溶液转变的焓变（23–51 kJ mol–1）与近期获得的其他凝胶形成体系的结果一致。
• Spectroscopic properties and gelling ability of a set of rod-like 2,3-disubstituted anthracenesElectronic supplementary information (ESI) available: UV absorption spectra of DDOA in 1-propanol and acetonitrile as a function of temperature; phase transition diagrams and related plots for DDOA in various solvents. See http://www.rsc.org/suppdata/nj/b3/b306961c/
  作者：Jean-Pierre Desvergne、Thierry Brotin、Danny Meerschaut、Gilles Clavier、Fr�d�ric Placin、Jean-Luc Pozzo、Henri Bouas-Laurent

  DOI：10.1039/b306961c

  日期：——

  The UV absorption spectra of 2,3-didecyloxyanthracene (DDOA) recorded in methanol, ethanol, 1-propanol, acetonitrile and methylcyclohexane reveal interesting features: they show a striking contrast between the isotropic solution and the gel state where, at ambient temperature, a fine structure appears with an apparent bathochromic shift (Δν ≈ −700 cm−1), as observed in the solid state. Such an effect was mimicked by 2,3-dioxydi- (and -tri-) methyleneanthracenes in which the conformational mobility of the two juxtanuclear oxygen atoms is reduced in a manner similar to that assumed in the gel state. The fluorescence emission of DDOA (10−5 M) at very low temperature exhibits a loss of fine structure and a bathochromic shift, for the gel state, in agreement with the presence of aggregates; the excitation spectra were found to be superimposable upon the absorption spectra of the isotropic and gel phases, respectively. Solvent screening for DDOA gelling ability has shown that the most efficient solvents are CH3OH and CH3CN. From the phase transition diagram (temperatures of gel setting, Tgel, and gel melting, Tm, versus concentration), thermodynamic parameters were derived: ΔH0gel/kJ mol−1 =  −70 (CH3OH), −66 (CH3CN); ΔS0gel/(J K−1 mol−1 = −147 (CH3OH), −140 (CH3CN) and ΔG0gel/kJ mol−1 (at 300 K) ≈ −26 (CH3OH), −24 (CH3CN). These parameters attest to the good stability of these gel systems. Finally, the influence of the chain length (n = C7H15 to C12H25) on the efficiency of gel formation (or melting) was investigated in methanol, ethanol, acetonitrile and heptane. It emerges that, to form gels, n-decyl and n-undecyl were found to be the most suitable chains and methanol and ethanol the most efficient solvents. It should be noted that the ability to form gels in methanol at a concentration of 0.6 mM at ambient temperature qualifies DDOA as a supergelator.

  2,3-二十烷氧基蒽（DDOA）在甲醇、乙醇、1-丙醇、乙腈和甲基环己烷中记录的紫外吸收光谱显示出有趣的特征：它们在各向同性溶液和凝胶状态之间呈现出显著的对比，在室温下，凝胶状态下出现了一种细微结构，并伴有明显的红移（Δν ≈ −700 cm−1），与固态下观察到的情况一致。这种效应在2,3-二氧二（和三）亚甲基蒽中得到了模拟，其中两个邻核氧原子的构象运动性以类似于假设的凝胶状态的方式减少。DDOA（10−5 M）在极低温下的荧光发射显示出细微结构的丧失和红移，这与聚集体的存在一致；激发光谱发现可与各向同性和凝胶相的吸收光谱重叠。对DDOA的凝胶能力进行溶剂筛选表明，最有效的溶剂是甲醇（CH3OH）和乙腈（CH3CN）。根据相变图（凝胶设置温度Tgel和凝胶熔化温度Tm与浓度的关系），得出了热力学参数：ΔH0gel/kJ mol−1 = −70（CH3OH），−66（CH3CN）；ΔS0gel/(J K−1 mol−1 = −147（CH3OH），−140（CH3CN）；ΔG0gel/kJ mol−1（在300 K下） ≈ −26（CH3OH），−24（CH3CN）。这些参数证明了这些凝胶体系的良好稳定性。最后，研究了链长（n = C7H15至C12H25）对凝胶形成（或熔化）效率的影响，结果显示，n-癸基和n-十一基是形成凝胶的最适合链，甲醇和乙醇是最有效的溶剂。值得注意的是，DDOA在室温下以0.6 mM的浓度在甲醇中形成凝胶的能力，使其成为一种超凝胶剂。
• Different synthetic routes towards efficient organogelators: 2,3-substituted anthracenes
  作者：Jean-Luc Pozzo、Gilles M. Clavier、Michel Colomes、Henri Bouas-Laurent

  DOI：10.1016/s0040-4020(97)00297-4

  日期：1997.5

  synthetic approaches towards 2,3-substituted anthracenes are reported and discussed in terms of selectivity and viability. This allowed us to introduce a variety of substituents as sidearms. Promising results have been found using a tandem Diels-Alder aromatization reaction using 2,3-dimethoxybutadiene 9 as a key intermediate. However, for multigram preparations the Friedel-Crafts approach is preferred

  报告了关于2，3-取代的蒽的三种合成方法，并在选择性和生存力方面进行了讨论。这使我们可以引入各种取代基作为侧链。使用串联的Diels-Alder芳构化反应（使用2,3-二甲氧基丁二烯9作为关键中间体）发现了令人鼓舞的结果。但是，对于多谱图制备，首选Friedel-Crafts方法。
• CRYOSCOPIC STUDIES ON THE TRANSITION POINTS OF THE COMPOUNDS OF ORGANIC SOLVENTS WITH SALTS. I
  作者：Hajime Osaka

  DOI：10.1246/bcsj.3.289

  日期：1928.11

  determined as 25.5°C. The method may be regarded as the cryoscopy using acetone with an artificially elevated melting point and can be used practically for the molecular weight determination. 2. A similar study has been carried out with HgCl2·CH3COCH3. The molecular depression has been determined as 24 and the transition point as 20.7°C. This system shows, however, some inaccuracy so that it can hardly be

  1. 研究了通过溶解外来物质使 NaI·3CH3COCH3 失去丙酮的转变点降低，分子压降为 100 克。丙酮的浓度已确定为 24.0。转变点也已确定为 25.5°C。该方法可视为使用人为升高熔点的丙酮的冷冻法，可实际用于分子量的测定。2. 对 HgCl2·CH3COCH3 进行了类似的研究。分子压降已确定为 24，转变点为 20.7°C。然而，该系统显示出一些不准确，因此它几乎不能应用于实际的冷冻检查。作者对片山 M. M. 教授表示衷心的感谢，在他的亲切指导下开展了这项工作。