2-amino-4-(3-nitrobenzoyl)-3-cyano-4H,5H-pyrano[3,2-c]chromen-5-one | 1613226-36-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 2-amino-4-(3-nitrobenzoyl)-3-cyano-4H,5H-pyrano[3,2-c]chromen-5-one
• 英文别名: 2-Amino-4-(3-nitrobenzoyl)-5-oxo-4h,5h-pyrano[3,2-c]chromene-3-carbonitrile；2-amino-4-(3-nitrobenzoyl)-5-oxo-4H-pyrano[3,2-c]chromene-3-carbonitrile
• CAS: 1613226-36-0
• 化学式: C₂₀H₁₁N₃O₆
• 分子量: 389.324
• InChiKey: GMRLXTKHIZKHTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  148
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  4-羟基香豆素 、 m-nitrophenylglyoxal monohydrate 、 丙二腈 在 ferrous ammonium sulfate hexahydrate 作用下， 以 乙醇 、 水 为溶剂， 反应 2.33h， 以85%的产率得到2-amino-4-(3-nitrobenzoyl)-3-cyano-4H,5H-pyrano[3,2-c]chromen-5-one
  参考文献：
  名称：

  One-pot, three-component synthesis of pyranocoumarins containing an aroyl group

  摘要：

  摘要：描述了一种快速制备含有芳酰基的吡喃香豆素的方法，通过4-羟基香豆素与芳基甘氧醛和丙二腈的三组分反应。该反应在莫尔氏盐的高效催化下进行，产物收率良好至优良，纯度高。该方法简单、廉价且环保。

  DOI：

  10.1515/hc-2014-0099

文献信息

• Synthesis of new 4-aroyl-pyrano[c]chromenes via a one-pot, three-component reaction based on aryl glyoxals
  作者：Saeed Khodabakhshi、Bahador Karami、Khalil Eskandari、Mahnaz Farahi

  DOI：10.1016/j.tetlet.2014.05.072

  日期：2014.7

  A new library of pyrano[c]chromenes containing an aroyl group has been synthesized by a novel multicomponent process involving the reaction of various aryl glyoxals with 4-hydroxycoumarin and malononitrile. The reactions were catalyzed efficiently by ammonium dihydrogen phosphate to yield the desired products in good to excellent yields.

  通过涉及多种芳基乙二醛与4-羟基香豆素和丙二腈反应的新型多组分方法，合成了一个含有芳酰基的吡喃并[ c ]二甲基苯酮的新文库。用磷酸二氢铵有效地催化反应，以良好或优异的产率得到所需产物。
• One-pot Synthesis of Novel Pyrano-Fused Coumarins Catalyzed by ZnO Nanoparticles
  作者：Saeed Khodabakhshi、Khalil Eskandari、Bahador Karami

  DOI：10.3987/com-14-13006

  日期：——

  A new class of pyrano [3,2-c]coumarins containing an aryloylgroup was synthesized via the three-component reactions of 4-hydroxycoumarin with arylglyoxals and malononitrile. The reactions are efficiently catalyzed by zinc oxide nanoparticles as powerful and recyclable catalyst. The green chemistry principles were also considered and the present method has some advantages, such as simplicity, low catalyst loading, and high yields.
• A New Three-Component Coupling reaction of Aryl Glyoxal, Malononitrile, and 4-Hydroxy Coumarin Catalysed by Recyclable Tio₂ nanoparticles
  作者：Saeed Khodabakhshi、Mozhgan Shahamirian、Mojtaba Baghernejad

  DOI：10.3184/174751914x14050999895192

  日期：2014.8

  Aryl glyoxals reacted with malononitrile and 4-hydroxycoumarin in the presence of a catalytic amount of TiO2 nanoparticles to give a hitherto unknown family of pyranochromenes in up to 80% yield. This new three-component reaction yielded some novel pyrano[3,2-c]chromene-5-ones containing an aroyl substituent. Using a recyclable and safe catalyst along with a green solvent system made the process eco-friendly and economic.