2-amino-4-(2-naphthoyl)-3-cyano-4H,5H-pyrano[3,2-c]chromen-5-one | 1613226-41-7

• 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-(2-naphthoyl)-3-cyano-4H,5H-pyrano[3,2-c]chromen-5-one
• 英文别名: 2-Amino-4-(2-naphthoyl)-5-oxo-4h,5h-pyrano[3,2-c]chromene-3-carbonitrile；2-amino-4-(naphthalene-2-carbonyl)-5-oxo-4H-pyrano[3,2-c]chromene-3-carbonitrile
• CAS: 1613226-41-7
• 化学式: C₂₄H₁₄N₂O₄
• 分子量: 394.386
• InChiKey: MHZCZWNLIXDARI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  30
• 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：
  102
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-羟基香豆素 、 2,2-二羟基-1-(2-萘)乙酮 、 丙二腈 在 磷酸二氢铵 作用下， 以 乙醇 、 水 为溶剂， 反应 1.17h， 以93%的产率得到2-amino-4-(2-naphthoyl)-3-cyano-4H,5H-pyrano[3,2-c]chromen-5-one
  参考文献：
  名称：

  基于芳基乙二醛的一锅三组分反应合成新的4-芳酰基-吡喃并[ c ]二甲基苯

  摘要：

  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。

  DOI：

  10.1016/j.tetlet.2014.05.072

文献信息

• One-pot, three-component synthesis of pyranocoumarins containing an aroyl group
  作者：Saeed Khodabakhshi、Fariba Jafari、Farzaneh Marahel、Mojtaba Baghernejad

  DOI：10.1515/hc-2014-0099

  日期：2014.10.1

  An expeditious method to prepare pyranocoumarins containing an aroyl group by the three-component reaction of 4-hydroxycoumarin with arylglyoxals and malononitrile is described. The reaction is efficiently catalyzed by Mohr’s salt, and the products were obtained in good to excellent yields with high purity. The method is simple, inexpensive, and environmentally friendly.

  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。
• 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.