2,3-methylenedioxyanthracene

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2,3-methylenedioxyanthracene
• 英文别名: anthra[2,3-d][1,3]dioxole；naphtho[2,3-f][1,3]benzodioxole
• 化学式: C₁₅H₁₀O₂
• 分子量: 222.243
• InChiKey: PYEVNXSPOAEZJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  17.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  2,3-二羥蒽醌 在 ammonium hydroxide 、 potassium carbonate 、 锌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2,3-methylenedioxyanthracene
  参考文献：
  名称：

  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/

  摘要：

  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。

  DOI：

  10.1039/b306961c

文献信息

• Lewis Acid/Brönsted Acid Mediated Benz-Annulation of Thiophenes and Electron-Rich Arenes
  作者：Settu Muhamad Rafiq、Ramakrishnan Sivasakthikumaran、Arasambattu K Mohanakrishnan

  DOI：10.1021/ol501006t

  日期：2014.5.16

  A facile preparation of benz-annulated heterocycles were achieved at rt involving a Lewis acid/Brönsted acid mediated annulation of heterocycles using 2,5-dimethoxytetrahydrofuran as a four-carbon synthon. The benz-/naphth-annulation was found to be successful with electron-rich arenes as well.

  在室温下，使用2，5-二甲氧基四氢呋喃作为四碳合成子，在路易斯酸/布朗斯台德酸介导的杂环环化中，实现了苯环式杂环的简便制备。还发现富电子芳烃也能成功实现苯并/萘环化。
• 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。