8-amino-5-hydroxy-4-methyl-2-oxo-10-(thiophen-2-yl)-2H,10Hpyrano[2,3-h]chromene-9-carbonitrile | 1365350-38-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 8-amino-5-hydroxy-4-methyl-2-oxo-10-(thiophen-2-yl)-2H,10Hpyrano[2,3-h]chromene-9-carbonitrile
• 英文别名: 8-Amino-5-hydroxy-4-methyl-2-oxo-10-(thiophen-2-yl)-2h,10h-pyrano[2,3-h]chromene-9-carbonitrile；8-amino-5-hydroxy-4-methyl-2-oxo-10-thiophen-2-yl-10H-pyrano[2,3-h]chromene-9-carbonitrile
• CAS: 1365350-38-4
• 化学式: C₁₈H₁₂N₂O₄S
• 分子量: 352.37
• InChiKey: DWBNVXQRVJROKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  134
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  间苯三酚 在 disodium hydrogenphosphate 作用下， 以 甲醇 为溶剂， 反应 1.67h， 生成 8-amino-5-hydroxy-4-methyl-2-oxo-10-(thiophen-2-yl)-2H,10Hpyrano[2,3-h]chromene-9-carbonitrile
  参考文献：
  名称：

  Alternative two-step route to khellactone analogues using silica tungstic acid and sodium hydrogen phosphate

  摘要：

  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。

  DOI：

  10.2478/s11696-013-0411-z

文献信息

• 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.
• 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.
• 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。