8-amino-10-(2-chlorophenyl)-5-hydroxy-2-oxo-4-phenyl-2H,10H-pyrano[2,3-h]chromene-9-carbonitrile | 1365350-77-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 8-amino-10-(2-chlorophenyl)-5-hydroxy-2-oxo-4-phenyl-2H,10H-pyrano[2,3-h]chromene-9-carbonitrile
• 英文别名: 8-Amino-10-(2-chlorophenyl)-5-hydroxy-2-oxo-4-phenyl-2h,10h-pyrano[2,3-h]chromene-9-carbonitrile；8-amino-10-(2-chlorophenyl)-5-hydroxy-2-oxo-4-phenyl-10H-pyrano[2,3-h]chromene-9-carbonitrile
• CAS: 1365350-77-1
• 化学式: C₂₅H₁₅ClN₂O₄
• 分子量: 442.858
• InChiKey: PVRXCALSJHLBJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  32
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  间苯三酚 、 苯甲酰乙酸乙酯 在 1-butyl-3-methylimidazolium hydroxide 、 (4-sulfobutyl)-tris(4-sulfophenyl)phosphonium hydrogen sulfate 作用下， 以 neat (no solvent) 为溶剂， 反应 3.27h， 生成 8-amino-10-(2-chlorophenyl)-5-hydroxy-2-oxo-4-phenyl-2H,10H-pyrano[2,3-h]chromene-9-carbonitrile
  参考文献：
  名称：

  Ionic-liquid-catalyzed green synthesis of coumarin derivatives under solvent-free conditions

  摘要：

  Bronsted acidic ionic liquids, namely 2-pyrrolidonium hydrogen sulfate, N-methyl-2-pyrrolidonium hydrogen sulfate, N-methyl-2-pyrrolidonium dihydrogen phosphate, (4-sulfobutyl)tris(4-sulfophenyl)phosphonium hydrogen sulfate, and triphenyl(propy1-3-sulfonyl)phosphonium toluenesulfonate, catalyzed efficient Pechmann condensation of phloroglucinol with beta-keto ethyl/methyl esters. 5,7-Dihydroxy-4-methylcoumarin and 5,7-dihydroxy-4-phenylcoumarin were prepared in good to excellent yields under mild, ambient, and solvent-free conditions. Pyrano[2,3-h] coumarins were then prepared by one-pot three-component reactions of 5,7-dihydroxy-4-subsituted coumarin, malononitrile, and aldehydes in the presence of catalytic amounts of Bronsted basic ionic liquids, namely 2-hydroxyethylammonium formate, 3-hydroxypropanaminium acetate, 1-butyl-3-methylimidazolium hydroxide, pyrrolidinium formate, and pyrrolidinium acetate, under thermal solvent-free conditions. The catalysts are environmentally benign and can be easily prepared, stored, and recovered without significant loss of activity. (C) 2013, Dalian Institute of Chemical Physics, Chinese Academy of Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/s1872-2067(12)60654-8

文献信息

• Alternative two-step route to khellactone analogues using silica tungstic acid and sodium hydrogen phosphate
  作者：Bahador Karami、Saeed Khodabakhshi、Khalil Eskandari

  DOI：10.2478/s11696-013-0411-z

  日期：2013.1.1

  A series of coumarins was synthesised via the silica tungstic acid-catalysed Pechmann reaction; some of these were employed for known three-component reactions with aromatic aldehydes and malononitrile in the presence of sodium hydrogen phosphate (Na2HPO4) as a basic catalyst, affording a variety of potentially anti-HIV active khellactone analogues.

  一系列香豆素通过硅钨酸催化的Pechmann反应合成；其中一些用于已知的三组分反应，与芳香醛和马来酸二腈在存在磷酸氢钠（Na2HPO4）作为碱性催化剂的情况下，生成各种潜在的抗HIV活性的赤花内酯类似物。
• Nano-Fe₃O₄@SiO₂-supported boron sulfonic acid as a novel magnetically heterogeneous catalyst for the synthesis of pyrano coumarins
  作者：Mahnaz Farahi、Bahador Karami、Raziyeh Keshavarz、Foroogh Khosravian

  DOI：10.1039/c7ra08253c

  日期：——

  magnetically heterogeneous catalyst based on the immobilization of boron sulfonic acid onto Fe3O4@SiO2 nanoparticles (Fe3O4@SiO2–BSA) is reported. Fe3O4@SiO2–BSA was characterized via FT-IR, X-ray diffraction patterns (XRD), scanning electron microscopy (SEM), energy-dispersive X-ray spectroscopy (EDS), and vibrating sample magnetometer (VSM) analysis. The performance ability of this catalyst including

  在这项研究中，报道了一种基于硼磺酸固定在Fe 3 O 4 @SiO 2纳米颗粒（Fe 3 O 4 @SiO 2 -BSA）上的新型磁性非均相催化剂。Fe 3 O 4 @SiO 2 –BSA通过FT-IR，X射线衍射图（XRD），扫描电子显微镜（SEM），能量色散X射线光谱（EDS）和振动样品磁力计（VSM）分析。在无溶剂条件下以高收率评估了该催化剂包括酸位点的性能，以合成吡喃香豆素。催化剂的热稳定性及其易于被磁场分离，使该催化剂成为良好的多相体系，并且是其他多相催化剂的有用替代品。
• A one-pot, three-component synthesis of new pyrano[2,3-h]coumarin derivatives
  作者：Bahador Karami、Saeed Khodabakhshi、Khalil Eskandari

  DOI：10.1016/j.tetlet.2012.01.024

  日期：2012.3

  The reaction between 5,7-dihydroxy-4-substituted coumarin, malononitrile, and aromatic aldehydes in the presence of a catalytic amount of K2CO3 as a basic catalyst leads to new pyrano[2,3-h]coumarin derivatives in good to excellent yields. (C) 2012 Elsevier Ltd. All rights reserved.
• Ionic-liquid-catalyzed green synthesis of coumarin derivatives under solvent-free conditions
  作者：Hamid Reza Shaterian、Morteza Aghakhanizadeh

  DOI：10.1016/s1872-2067(12)60654-8

  日期：2013.9

  Bronsted acidic ionic liquids, namely 2-pyrrolidonium hydrogen sulfate, N-methyl-2-pyrrolidonium hydrogen sulfate, N-methyl-2-pyrrolidonium dihydrogen phosphate, (4-sulfobutyl)tris(4-sulfophenyl)phosphonium hydrogen sulfate, and triphenyl(propy1-3-sulfonyl)phosphonium toluenesulfonate, catalyzed efficient Pechmann condensation of phloroglucinol with beta-keto ethyl/methyl esters. 5,7-Dihydroxy-4-methylcoumarin and 5,7-dihydroxy-4-phenylcoumarin were prepared in good to excellent yields under mild, ambient, and solvent-free conditions. Pyrano[2,3-h] coumarins were then prepared by one-pot three-component reactions of 5,7-dihydroxy-4-subsituted coumarin, malononitrile, and aldehydes in the presence of catalytic amounts of Bronsted basic ionic liquids, namely 2-hydroxyethylammonium formate, 3-hydroxypropanaminium acetate, 1-butyl-3-methylimidazolium hydroxide, pyrrolidinium formate, and pyrrolidinium acetate, under thermal solvent-free conditions. The catalysts are environmentally benign and can be easily prepared, stored, and recovered without significant loss of activity. (C) 2013, Dalian Institute of Chemical Physics, Chinese Academy of Sciences. Published by Elsevier B.V. All rights reserved.