5-acetyl-2-amino-6-methyl-4-(4-nitrophenyl)-4H-pyran-3-carbonitrile | 304868-17-5

• 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-(4-nitrophenyl)-4H-pyran-3-carbonitrile
• 英文别名: 5-acetyl-2-amino-3-cyano-6-methyl-4-(4-nitrophenyl)-4H-pyran
• CAS: 304868-17-5
• 化学式: C₁₅H₁₃N₃O₄
• 分子量: 299.286
• InChiKey: ZAGROISUWIQWLU-UHFFFAOYSA-N

物化性质

• 沸点：
  582.0±50.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

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-(4-nitrophenyl)-4H-pyran-3-carbonitrile 在 水 、 对甲苯磺酸 作用下， 反应 2.5h， 以87%的产率得到5-acetyl-6-methyl-4-(4-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：

  对硝基苯甲醛 、 乙酰丙酮 、 丙二腈 在 ClOZn^(1-)*2CH₄N₂O*C₅H₁₄NO⁽¹⁺⁾ 作用下， 以 neat liquid 为溶剂， 反应 0.5h， 以92%的产率得到5-acetyl-2-amino-6-methyl-4-(4-nitrophenyl)-4H-pyran-3-carbonitrile
  参考文献：
  名称：

  通过纳米ZnO，尿素和氯化胆碱的三种固体的杂交制备优异的液体催化剂，用于Knoevenagel基反应

  摘要：

  摘要[ZnClO.urea] - [Ch.urea] +的复合催化剂是通过将纳米ZnO在50°C的氯化胆碱：2urea中溶解而制备的。[ZnClO.urea]的浓度-给定液体中的ZnO含量为19,987 ppm，比由本体ZnO制成的类似溶液高10.5倍。这种有机/无机杂化催化剂在基于Knoevenagel的吡喃，苯并二氢吡喃和缺电子烯烃的合成中表现出很高的催化性能。由于ZnO纳米粒子在DES中的高度扩散，纳米ZnO与DES的协同作用以及这种流体催化剂与起始原料的大量接触，因此所有Knoevenagel基反应均以较低的催化剂负载量和较高的收率进行，比单独的ChCl：2urea短，纳米ZnO，或什至以前用于此目的的催化剂。高极性和可重复使用性是阴离子络合物[ZnClO.urea] -和纳米ZnO形状均一的其他优点。 图形概要

  DOI：

  10.1007/s13738-017-1144-7

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
• Meglumine: A Novel and Efficient Catalyst for One-Pot, Three-Component Combinatorial Synthesis of Functionalized 2-Amino-4<i>H</i>-pyrans
  作者：Rui-Yun Guo、Zhi-Min An、Li-Ping Mo、Rui-Zhi Wang、Hong-Xia Liu、Shu-Xia Wang、Zhan-Hui Zhang

  DOI：10.1021/co400107j

  日期：2013.11.11

  An efficient one-pot synthesis of functionalized 2-amino-4H-pyrans by a meglumine-catalyzed three-component reaction has been developed. A broad range of substrates including aromatic and heteroaromatic aldehydes, isatin derivatives, and acenaphthenequinone are condensed with enolizable C-H activated compounds and alkylmalonates to give the desired products in high to excellent yields. This methodology provides an alternative approach for rapid access to construct a diversity-oriented library of 4H-pyrans.
• Preparation of a superior liquid catalyst by hybridization of three solids of nanoZnO, urea, and choline chloride for Knoevenagel-based reactions
  作者：Fatemeh Tamaddon、Davood Azadi

  DOI：10.1007/s13738-017-1144-7

  日期：2017.10

  electron-deficient alkenes. Due to the high diffusion of ZnO nanoparticles in DESs, synergy of nanoZnO with DESs, and much contact of this fluid catalyst with starting materials, all Knoevenagel-based reactions occur with higher yields at lower catalyst loading and shorter times than individual ChCl:2urea, nanoZnO, or even previously catalysts used for this purpose. High polarity and reusability are other

  摘要[ZnClO.urea] - [Ch.urea] +的复合催化剂是通过将纳米ZnO在50°C的氯化胆碱：2urea中溶解而制备的。[ZnClO.urea]的浓度-给定液体中的ZnO含量为19,987 ppm，比由本体ZnO制成的类似溶液高10.5倍。这种有机/无机杂化催化剂在基于Knoevenagel的吡喃，苯并二氢吡喃和缺电子烯烃的合成中表现出很高的催化性能。由于ZnO纳米粒子在DES中的高度扩散，纳米ZnO与DES的协同作用以及这种流体催化剂与起始原料的大量接触，因此所有Knoevenagel基反应均以较低的催化剂负载量和较高的收率进行，比单独的ChCl：2urea短，纳米ZnO，或什至以前用于此目的的催化剂。高极性和可重复使用性是阴离子络合物[ZnClO.urea] -和纳米ZnO形状均一的其他优点。 图形概要
• 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.