3-甲基-1-苯基-1H-吡唑并[3,4-b]喹啉 | 894-88-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 3-甲基-1-苯基-1H-吡唑并[3,4-b]喹啉
• 英文名称: 3-methyl-1-phenyl-1H-pyrazolo[3,4-b]quinoline
• 英文别名: 3-methyl-1-phenylpyrazolo<3,4-b>quinoline；3-methyl-1-phenylpyrazolo[3,4-b]quinoline
• CAS: 894-88-2
• 化学式: C₁₇H₁₃N₃
• 分子量: 259.31
• InChiKey: VXXHCSZPRKRCKI-UHFFFAOYSA-N

物化性质

• 熔点：
  178 °C
• 沸点：
  394.2±24.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-methyl-4-(2'-nitrobenzylidene)-1-phenylpyrazolin-5-one 在 铁粉 、 溶剂黄146 作用下， 反应 0.5h， 以60%的产率得到3-甲基-1-苯基-1H-吡唑并[3,4-b]喹啉
  参考文献：
  名称：

  Danel, A.; Tomasik, P., Polish Journal of Chemistry, 1995, vol. 69, # 7, p. 1013 - 1017

  摘要：

  DOI：

文献信息

• DMSO as a Methine Source in TFA-Mediated One-Pot Tandem Regioselective Synthesis of 3-Substituted-1-Aryl-1<i>H</i>-Pyrazolo-[3,4-<i>b</i>]quinolines from Anilines and Pyrazolones
  作者：Pushpendra Yadav、Annapurna Awasthi、Sabapathi Gokulnath、Dharmendra Kumar Tiwari

  DOI：10.1021/acs.joc.0c02696

  日期：2021.2.5

  well as solvent making this process an environmentally benign approach. A broad range of diversely substituted aryl amines and pyrazolines are successfully employed in this reaction to access a series of pyrazolo[4,3-c]quinolones through a novel cascade mechanism. Furthermore, the application and mechanistic studies of the present methodology also demonstrated.

  酸介导和DMSO参与者从容易获得的苯胺和吡唑啉酮一锅式串联合成3-取代的1-芳基-1 H-吡唑并-[3,4- b ]喹啉。这种方法能够在无过渡金属和无氧化剂的条件下区域选择性构建有价值的杂环，其中DMSO充当次甲基源以及溶剂，使该方法成为环境友好的方法。在该反应中成功地使用了各种不同取代的芳基胺和吡唑啉，以通过新颖的级联机制访问一系列吡唑并[4,3- c ]喹诺酮。此外，还证明了本方法的应用和机理研究。
• Facile and Regioselective Synthesis of Substituted 1<i>H</i>‐Pyrazolo[3,4‐<i>b</i>]quinolines from 2‐Fluorobenzaldehydes and 1<i>H</i>‐Pyrazol‐5‐amines
  作者：Paweł Szlachcic、Mateusz Kucharek、Bożena Jarosz、Andrzej Danel、Katarzyna Stadnicka

  DOI：10.1002/jhet.2751

  日期：2017.5

  The present article concerns the scope and limitations of the regioselective condensation of 2‐fluorobenzaldehydes with 1H‐pyrazol‐5‐amines, leading to the synthesis of substituted 1H‐pyrazolo[3,4‐b]quinolines (PQ), in the presence of a base catalyst (DABCO and 2,4,6‐trimethylpyridine). A method to obtain these nitrogen heterocycles with fluorine or trifluoromethyl substituents in different positions

  本文涉及2-氟苯甲醛与1 H-吡唑-5-胺的区域选择性缩合的范围和局限性，导致取代的1 H-吡唑并[3,4- b ]喹啉（PQ）的合成。存在碱催化剂（DABCO和2,4,6-三甲基吡啶）。系统地研究了含氟取代基对PQ参数的影响，研究了一种获得碳环上不同位置具有氟或三氟甲基取代基的氮杂环的方法。的那些化合物，其特征在于高的荧光强度，经测试作为发光体的有机发光二极管自1997年以来的官能PQ引起各种参数的变化，例如，HOMO和LUMO能级，这对调整重要人造有机发光二极管。PQ制备最简单的方法之一，即取代的苯胺与5-氯-1 H-吡唑-4-甲醛的缩合反应不是区域选择性的。这项研究中描述的方法可以合成1 H吡唑并[3,4- b具有高收率和高选择性的]喹啉–仅获得预期的异构体。由于可以从市场上购买到各种不同的2-氟苯甲醛，并且易于制备具有不同取代基的1 H-吡唑-5-胺，因此该方法可以替代已知方法。还详细研究了反应的所有可能机理。
• A simple and efficient synthesis of 1,3,6-trisubstituted pyrazoloquinolines via intramolecular cyclization – optimization studies
  作者：Mateusz Kucharek、Andrzej Danel、Arkadiusz Gut

  DOI：10.1007/s10593-022-03127-1

  日期：2022.11

  In this work, we developed a straightforward and convenient method for the synthesis of substituted pyrazoloquinolines – highly desirable compounds for many high-tech and biomedical applications. On the basis of intramolecular cyclization of 5-(N-aryl)aminopyrazoles in the presence of DMF diethyl acetal and POCl3, a series of differently substituted pyrazoloquinolines were synthesized. The synthetic

  在这项工作中，我们开发了一种简单方便的方法来合成取代的吡唑并喹啉——许多高科技和生物医学应用中非常理想的化合物。以5-( N-芳基)氨基吡唑在DMF二乙缩醛和POCl 3存在下的分子内环化为基础，合成了一系列不同取代的吡唑并喹啉。考虑到甲酰化剂的类型（DMF与. DMF 二乙基二缩醛）、反应温度和所用试剂的化学计量。由于其多功能性、简单性和易于纯化获得的产品，这种合成方法为吡唑并喹啉基功能材料的合理设计提供了有价值的指导。
• Microwave Assisted FriedläNder Condensation Catalyzed by Clay
  作者：Gowravaram Sabitha、R. Satheesh Babu、B. V. Subba Reddy、J. S. Yadav

  DOI：10.1080/00397919908086603

  日期：1999.12.1

  Clay catalyzed Friedlander condensation of 2-amino arylaldehyde or ketone with carbonyl compounds containing a-methylene group has been achieved in solvent free condition under microwave irradiation to give polycyclic quinoline derivatives.
• Synthesis, electrochemical, photophysical, and electroluminescent properties of organic dyes containing pyrazolo[3, 4-b]quinoline chromophore
  作者：Wen Wan、Huibin Wang、Hong Lin、Jing Wang、Yuansong Jiang、Haizhen Jiang、Shizheng Zhu、Zixing Wang、Jian Hao

  DOI：10.1016/j.dyepig.2015.05.002

  日期：2015.10

  Organic dyes containing trifluoromethylated-pyrazolo[3, 4-b]quinoline were synthesized by using condensation reaction between substituted pyrazolo-4-formaldehyde and aryl amines in moderate yields. Quantum calculation, electrochemical, photophysical, and electroluminescent properties were discussed in detail. Electron-withdrawing groups at 6-position of dyes stabilized the LUMO energy levels significantly resulting in red-shifted absorption/emission spectra. Addition of electron-donating group destabilized the HOMO strongly and the LUMO energy levels slightly resulting in red-shifted absorption maxima, but in blue-shifted emission maxima. Experimental and quantum calculation results are presented here to explain this unusual phenomenon. A linear relationship of dipole moments versus Stokes shifts is obtained for these fluorophores, where the increase of dipole moment is accompanied by a decrease in Stokes shift. Organic light-emitting diodes based on selected dyes showed emission at 456 nm, maximum external quantum efficiency at 1.43%, and current efficiency at 1.95 cd/A. (C) 2015 Elsevier Ltd. All rights reserved.