5-acetyl-2-amino-6-methyl-4-(3-nitrophenyl)-4H-pyran-3-carbonitrile

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-acetyl-2-amino-6-methyl-4-(3-nitrophenyl)-4H-pyran-3-carbonitrile
• 化学式: C₁₅H₁₃N₃O₄
• 分子量: 299.286
• InChiKey: NFYZZXXTHXRSJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  122
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-acetyl-2-amino-6-methyl-4-(3-nitrophenyl)-4H-pyran-3-carbonitrile 在 水 、 对甲苯磺酸 作用下， 反应 2.5h， 以88%的产率得到5-acetyl-6-methyl-4-(3-nitro-phenyl)-2-oxo-1,2,3,4-tetrahydro-pyridine-3-carbonitrile
  参考文献：
  名称：

  Nano crystalline ZnO catalyzed one pot multicomponent reaction for an easy access of fully decorated 4H-pyran scaffolds and its rearrangement to 2-pyridone nucleus in aqueous media

  摘要：

  A green and highly efficient protocol has been developed for the synthesis of 4H-pyran scaffolds installing a one-pot three-component coupling reaction of an aldehyde, malononitrile, and a 1,3-diketo compound using nano structured ZnO as the catalyst in aqueous alcoholic medium. A greener method to synthesize 3,4-dihydropyridin-2-one has also been developed by rearranging 4H-pyran derivatives in aqueous medium applying p-TSOH as the right catalyst source. A wide spectrum of functional groups was tolerated in both the developed synthetic protocols with good to excellent yield of the targeted molecules. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.06.086
• 作为产物：
  描述：

  间硝基苯甲醛 、 乙酰丙酮 、 丙二腈 在 L-缬氨酸 作用下， 以 水 为溶剂， 反应 0.75h， 以94%的产率得到5-acetyl-2-amino-6-methyl-4-(3-nitrophenyl)-4H-pyran-3-carbonitrile
  参考文献：
  名称：

  有机催化介导的绿色方法：一种多功能的新型 L-缬氨酸促进了多种密集功能化的 2-amino-3-cyano-4H-pyrans 的合成

  摘要：

  摘要：新型 L-缬氨酸的发现促进了多种 2-氨基-3-氰基-4H-吡喃的简便、多功能绿色合成，使用芳香醛、丙二腈和多种富电子可烯醇化羰基化合物的单锅多组分串联反应被描述。据我们所知，这是关于在有机合成中使用天然 L-缬氨酸作为催化剂的第一份报告。环境友好、反应条件温和、使用容易获得的廉价原料、反应时间短、产率高、原子经济性高和有机催化剂的可回收性是所公开方案的主要优点。图形概要

  DOI：

  10.1080/00397911.2017.1393087

文献信息

• Organocatalytic mediated green approach: A versatile new <scp>L</scp>-valine promoted synthesis of diverse and densely functionalized 2-amino-3-cyano-4H-pyrans
  作者：Jyoti Tiwari、Swastika Singh、Mohammad Saquib、Fatima Tufail、Amit Kumar Sharma、Shailesh Singh、Jaya Singh、Jagdamba Singh

  DOI：10.1080/00397911.2017.1393087

  日期：2018.1.17

  new L-valine promoted facile and versatile green synthesis of diversified 2-amino-3-cyano-4H-pyrans using a one pot multicomponent-tandem reaction of aromatic aldehydes, malononitrile, and diverse electron-rich enolizable carbonyl compounds is described. To the best of our knowledge this is the first report on the use of native L-valine as a catalyst in organic synthesis. Environmental friendly, mild

  摘要：新型 L-缬氨酸的发现促进了多种 2-氨基-3-氰基-4H-吡喃的简便、多功能绿色合成，使用芳香醛、丙二腈和多种富电子可烯醇化羰基化合物的单锅多组分串联反应被描述。据我们所知，这是关于在有机合成中使用天然 L-缬氨酸作为催化剂的第一份报告。环境友好、反应条件温和、使用容易获得的廉价原料、反应时间短、产率高、原子经济性高和有机催化剂的可回收性是所公开方案的主要优点。图形概要
• Tetramethylguanidine-[bmim][BF4]. An Efficient and Recyclable Catalytic System for One-Pot Synthesis of 4H-Pyrans
  作者：Yanqing Peng、Gonghua Song、Feifei Huang

  DOI：10.1007/s00706-004-0270-y

  日期：2005.5

  A clean and efficient method for the synthesis of 4 H -pyran derivatives through the one-pot condensation of aromatic aldehydes, malononitriles, and β-dicarbonyl compounds, using guanidine base tetramethylguanidine in [ bmim ][BF4] ionic liquid as a recyclable catalytic system, was described.

  一种清洁有效的方法，通过在[ bmim ] [BF 4 ]离子液体中使用胍基四甲基胍作为可循环使用的催化剂，通过芳族醛，丙二腈和β-二羰基化合物的一锅缩合来合成4 H- 吡喃衍生物 系统，进行了描述。
• A simple and convenient approach to the Friedländer synthesis of pyrano[2,3-b]pyridines
  作者：Nagarajan Panneer Selvam、Thelagathoti Hari Babu、Paramasivan T. Perumal

  DOI：10.1016/j.tet.2009.08.025

  日期：2009.10

  SnCl2·2H2O mediated efficient synthesis of pyrano[2,3-b]pyridines was achieved by the Friedländer reaction of 2-amino-3-cyano-4H-pyrans with cyclopentanone/cyclohexanone under solvent-free condition.

  在无溶剂条件下，通过2-氨基-3-氰基-4 H-吡喃与环戊酮/环己酮的Friedländer反应，实现了SnCl 2 ·2H 2 O介导的吡喃并[2,3- b ]吡啶的高效合成。
• Efficient Three-Component One-Pot Synthesis of 4H-Pyrans
  作者：J. Malviya、S. Kala、L. K. Sharma、R. K. P. Singh

  DOI：10.1134/s1070428019050178

  日期：2019.5

  Clean, practical, and efficient electrochemical synthesis of pharmaceutically relevant 4H-pyran derivatives by one-pot three-component combination of an aryl aldehyde, malononitrile, and a dicarbonyl compoundis developed. The synthesis is performed in ethanol with lithium perchlorate as a supporting electrolyte in an undivided cell on a platinum electrode under constant potential electrolysis conditions.
• Nano crystalline ZnO catalyzed one pot multicomponent reaction for an easy access of fully decorated 4H-pyran scaffolds and its rearrangement to 2-pyridone nucleus in aqueous media
  作者：Pranabes Bhattacharyya、Koyel Pradhan、Sanjay Paul、Asish R. Das

  DOI：10.1016/j.tetlet.2012.06.086

  日期：2012.8

  A green and highly efficient protocol has been developed for the synthesis of 4H-pyran scaffolds installing a one-pot three-component coupling reaction of an aldehyde, malononitrile, and a 1,3-diketo compound using nano structured ZnO as the catalyst in aqueous alcoholic medium. A greener method to synthesize 3,4-dihydropyridin-2-one has also been developed by rearranging 4H-pyran derivatives in aqueous medium applying p-TSOH as the right catalyst source. A wide spectrum of functional groups was tolerated in both the developed synthetic protocols with good to excellent yield of the targeted molecules. (c) 2012 Elsevier Ltd. All rights reserved.