N-[(4-nitrophenyl)(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]acetamide | 1092452-49-7

• 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: N-[(4-nitrophenyl)(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]acetamide
• 英文别名: N-[(4-hydroxy-2-oxochromen-3-yl)-(4-nitrophenyl)methyl]acetamide
• CAS: 1092452-49-7
• 化学式: C₁₈H₁₄N₂O₆
• 分子量: 354.319
• InChiKey: ZKXJMDRTUMOINE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  乙酰胺 、 4-羟基香豆素 、 对硝基苯甲醛 在 对甲苯磺酸 作用下， 以 neat (no solvent) 为溶剂， 反应 4.5h， 以90%的产率得到N-[(4-nitrophenyl)(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]acetamide
  参考文献：
  名称：

  3-( α-酰氨基苄基)4-羟基香豆素衍生物的新型高效三组分一锅法合成

  摘要：

  对甲苯磺酸在无溶剂条件下催化4-羟基香豆素、芳香醛和酰胺的三组分反应为合成3-(α-酰氨基苄基)-4-羟基香豆素衍生物提供了一种简单有效的一锅法以优异的产量。

  DOI：

  10.3184/174751912x13518648205073

文献信息

• An Efficient Synthesis of Functionalized 3-(α-amidobenzyl)- 4-hydroxycoumarin Derivatives by ZnO Nanoparticles Promoted Condensation Reaction Between Aromatic Aldehyde, 4-hydroxycoumarin, and Amides
  作者：Hossein Anaraki-Ardakani、Abbas charooseai

  DOI：10.13005/ojc/310324

  日期：2015.9.24

  An efficient and green protocol for the synthesis of 3-(α-amidobenzyl)-4-hydroxycoumarin derivatives by one pot, three component coupling reaction of aromatic aldehyde, 4hydroxycoumarin, and amides has been developed using ZnO nanoparticles (NPs) as the catalyst. The procedure is formed in high yields, short reaction time and an environmentally friendly specificity.

  使用ZnO纳米粒子（NPs）作为催化剂，开发了一种通过一锅，芳香醛，4-羟基香豆素和酰胺的三组分偶联反应合成3-（α-氨基苄基）-4-羟基香豆素衍生物的有效且绿色的方案。该方法以高收率，短反应时间和环境友好的特异性形成。
• Synthesis of 3-[(acetylamino)(aryl)methyl]-4-Hydroxycoumarins
  作者：Mohammad Anary-Abbasinejad、Hossein Anaraki-Ardakani、Azimeh Saidipoor、Mahmood Shojaee

  DOI：10.3184/030823407x247785

  日期：2007.9

  One-pot, three-component reaction between aryl aldehydes, 4-hydroxycoumarin, and acetonitrile in the presence of chlorosulfonic acid affords 3-[(acetylamino)(aryl)methyl]-4-hydroxycoumarins in excellent yields.

  在氯磺酸的存在下，芳基醛、4-羟基香豆素和乙腈之间的一锅三组分反应以极好的收率提供了 3-[(乙酰氨基)(芳基)甲基]-4-羟基香豆素。
• P₂O₅-Hexamethyldisiloxane (HMDS): An Efficient System to Induce the Three-Component Reaction of Enolic Systems, Aromatic Aldehydes, and Acetonitrile
  作者：Mohammad Anary-Abbasinejad、Hossein Anaraki-Ardakani、Alireza Hassanabadi

  DOI：10.1080/00397910802213778

  日期：2008.10.22

  Three-component reaction of an enolizable compound, such as acetophenone, methyl acetoacetate, 4-hydroxycoumarin, 2-naphthol, or 3-hydroxy-2-naphthoic acid; an aromatic aldehyde, and acetonitrile induced by phosphorus pentoxide and hexamethyldisiloxane leads to 2-acetylamino ketones, methyl 3-(acetylamino aryl methyl)-3-oxobutanoates, 3-(acetylamino aryl methyl)-4-hydroxycoumarins, 1-(acetylamino aryl methyl)-2-naphthols, or 4-(acetylamino aryl methyl)-3-hydroxy-2-naphthoic acids in excellent yields.
• An efficient and green protocol for the one-pot synthesis of 3-amido-alkyl-4-hydroxycoumarin derivatives by choline chloride/urea as a deep eutectic solvent
  作者：Hamed ASADI、Hossein ANARAKI-ARDAKANI、Parviz TORABI、Narghes TAHERI

  DOI：10.33224/rrch.2020.65.9.05

  日期：——

  A green and highly efficient synthesis of some 3-amido-alkyl-4-hydroxycoumarin derivatives by one-pot, three-component reaction of aryl aldehydes, 4-hydroxycoumarin, or 4-hydroxy-6-methylpyran-1-one, and amides in deep eutectic solvent (DES) is reported. The DES system offers advantages in terms of environmental benign, biodegradable, short reaction times, and high yield. DES can be easily recovered and can be reused for other runs without any reduction in the activity.
• Novel Efficient Three-Component, One-Pot Synthesis of 3-(α-amidobenzyl)-4-hydroxycoumarin derivatives
  作者：Masud Malekpour、Hossein Anaraki-Ardakani、Maziar Noei

  DOI：10.3184/174751912x13518648205073

  日期：2012.12

  The three-component reaction between 4-hydroxycoumarin, aromatic aldehydes and amides catalysed by p-toluenesulfonic acid in solvent-free conditions provided a simple and efficient one-pot route for the synthesis of 3-(α-amidobenzyl)-4-hydroxycoumarin derivatives in excellent yields.

  对甲苯磺酸在无溶剂条件下催化4-羟基香豆素、芳香醛和酰胺的三组分反应为合成3-(α-酰氨基苄基)-4-羟基香豆素衍生物提供了一种简单有效的一锅法以优异的产量。