2-Amino-6-(hydroxymethyl)-8-oxo-4-(4-pyridinyl)-4,8-dihydropyrano[3,2-b]pyran-3-carbonitrile | 625376-10-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 2-Amino-6-(hydroxymethyl)-8-oxo-4-(4-pyridinyl)-4,8-dihydropyrano[3,2-b]pyran-3-carbonitrile
• 英文别名: 2-amino-6-(hydroxymethyl)-8-oxo-4-pyridin-4-yl-4H-pyrano[3,2-b]pyran-3-carbonitrile
• CAS: 625376-10-5
• 化学式: C₁₅H₁₁N₃O₄
• 分子量: 297.27
• InChiKey: FGVLMYOPSKMFKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-吡啶甲醛 、 曲酸 、 丙二腈 在 silica nanospheres-supported ferrocene-containing ionic liquid 作用下， 以 乙醇 、 水 为溶剂， 反应 0.25h， 以85%的产率得到2-Amino-6-(hydroxymethyl)-8-oxo-4-(4-pyridinyl)-4,8-dihydropyrano[3,2-b]pyran-3-carbonitrile
  参考文献：
  名称：

  Ferrocene-Containing Ionic Liquid Supported on Silica Nanospheres (SiO₂@Imid-Cl@Fc) as a Mild and Efficient Heterogeneous Catalyst for the Synthesis of Pyrano[3,2-b]Pyran Derivatives Under Ultrasound Irradiation

  摘要：

  设计并合成了一种新型异相二氧化硅纳米球支撑的含二茂铁离子液体催化剂（SiO2@Imid-Cl@Fc），并通过傅立叶变换红外光谱（FTIR）、场发射扫描电子显微镜（FE-SEM）、能量色散 X 射线（EDX）和 X 射线衍射（XRD）分析对其进行了系统表征。在室温、超声辐照条件下，测试了 SiO2@Imid-Cl@Fc 催化剂在丙二腈和曲酸与 15 种芳香醛的一锅三组分反应中的催化活性。反应产物为吡喃并[3,2-b]吡喃衍生物，其中四种为新产物。该催化剂在较短的反应时间（15-20 分钟）内表现出良好的催化性能，可循环使用至少五次而不会明显丧失活性。

  DOI：

  10.3184/174751918x15161933697754

文献信息

• Synthesis of pyridinium-based salts: Catalytic application at the synthesis of six membered O-heterocycles
  作者：Saeed Babaee、Mohammad Ali Zolfigol、Mahmoud Zarei、Maryam Abbasi、Zahra Najafi

  DOI：10.1016/j.mcat.2019.110403

  日期：2019.10

  [PySO3H]FeCl4 as a magnetic molten salts was also investigated. Three categories of six membered O-heterocyclic compounds such as 2-amino-4H-chromene, 2-amino-4,8-dihydropyrano and 2-amino-4H-pyrans were prepared in the presence of a catalytic amount of the above said molten salts. These synthesized O-heterocyclic compounds are highly regarded due to their biological activities.

  本文设计，合成并充分表征了一系列具有各种抗衡离子的吡啶鎓离子液体（IL）和熔融盐（MS）。这些新的离子液体和熔融盐是通过[PySO 3 H] Cl与AlCl 3，FeCl 3，NaBF 4和KPF 6反应制备的，以生产所需的催化剂[PySO 3 H] X（X = AlCl 4，FeCl 4，BF 4和PF 6）。这些催化剂的结构通过FT-IR，NMR（1 H，13 C，27 Al，19F）和质谱，以及使用XRD，SEM，TG，DTG和DTA技术。还研究了[PySO 3 H] FeCl 4作为磁性熔融盐的磁性测量（VSM）。在催化量的上述物质的存在下制备了三类六元O-杂环化合物，例如2-氨基-4 H-色烯，2-氨基-4,8-​​二氢吡喃和2-氨基-4 H-吡喃。所说的熔盐。这些合成的O-杂环化合物由于其生物活性而受到高度重视。
• SiO₂–OSO₃H Nanoparticles: An Efficient, Versatile and New Reagent for the One-Pot Synthesis of 2-Amino-8-Oxo-4,8-Dihydropyrano[3,2-<i>b</i>]Pyran-3-Carbonitrile Derivatives in Water, a Green Protocol
  作者：Bahareh Sadeghi、Parinaz Farokhi Nezhad、Saeedeh Hashemian

  DOI：10.3184/174751914x13866053657371

  日期：2014.1

  In a one-pot three-component reaction, an aromatic or aliphatic aldehyde, malononitrile and 5-hydroxy-2-hydroxymethyl-4H-pyran-4-one were condensed for the synthesis of 2-amino-8-oxo-4,8-dihydropyrano[3,2- b]pyran-3-carbonitrile derivatives in the presence of nano-silica sulfuric acid (SiO₂–OSO₃H nanoparticles) in improved yields. The catalyst is recoverable by simple filtration and can be used in the subsequent reactions.

  在纳米二氧化硅硫酸（SiO2-OSO3H 纳米粒子）存在下，通过一锅三组份反应，缩合芳香族或脂肪族醛、丙二腈和 5-羟基-2-羟甲基-4H-吡喃-4-酮，合成 2-氨基-8-氧代-4,8-二氢吡喃并[3,2-b]吡喃-3-甲腈衍生物，收率提高。催化剂可通过简单过滤回收，并可用于后续反应。
• Efficient synthesis of new pyrano[3,2-<i>b</i>]pyran derivatives via Fe₃O₄@SiO₂-IL-Fc catalyzed three-component reaction
  作者：Reza Teimuri-Mofrad、Somayeh Esmati、Masoumeh Rabiei、Mahdi Gholamhosseini-Nazari

  DOI：10.1515/hc-2017-0140

  日期：2017.12.20

  patterns (XRD), energy-dispersive X-ray spectroscopy (EDX) and field emission scanning electron microscopy (FE-SEM). The novel nanomagnetic catalyst was used in the one-pot synthesis of pyrano[3,2-b]pyran derivatives by the three-component reaction of various aldehydes, malononitrile and kojic acid or chlorokojic acid at room temperature under ultrasonic irradiation. This new method has many advantages such

  摘要 合成了负载在二氧化硅包覆的 Fe3O4 磁性纳米粒子（纳米 Fe3O4@SiO2-IL-Fc）上的含二茂铁离子液体，这是一种新型的多相纳米催化剂。通过傅里叶变换红外光谱（FT-IR）、X射线衍射图（XRD）、能量色散X射线光谱（EDX）和场发射扫描电子显微镜（FE-SEM）对催化剂的结构进行表征。将新型纳米磁性催化剂用于各种醛类、丙二腈和曲酸或氯曲酸在室温下在超声辐照下的三组分反应，一锅法合成吡喃并[3,2-b]吡喃衍生物。这种新方法具有许多优点，例如简单、反应时间短、收率高、易于后处理和易于纯化。还，
• s-Triazinium-based ionic liquid immobilized on silica-coated Fe3O4 magnetic nanoparticles: an efficient and magnetically separable heterogeneous catalyst for synthesis of 2-amino-4,8-dihydropyrano[3,2-b]pyran-3-carbonitrile derivatives for antioxidant and antifungal evaluation studies
  作者：Davood Azarifar、Hakimeh Ebrahimiasl、Roya Karamian、Masoumeh Ahmadi-Khoei

  DOI：10.1007/s13738-018-1521-x

  日期：2019.2

  method, vibrating sample magnetometery and thermo-gravimetric analysis. These nanoparticles were identified as an efficient catalyst for one-pot three-component synthesis of 4,8-dihydropyrano[3,2-b]pyran derivatives in excellent yields. The catalyst was easily separated by magnetic decantation, and the recovered nanoparticles were reused for four fresh runs without any significant loss of catalytic activity

  我们已经描述了一种新的方法，以heterogenize小号通过容易制备的离子液体为基础的催化剂嗪小号嗪固定二氧化硅涂布的Fe 3 ö 4的磁性纳米颗粒的[Fe 3 ö 4 @SiO 2 -小号-triazinium氯化物]。通过傅立叶变换红外光谱，X射线粉末衍射，扫描电子显微镜，透射电子显微镜，能量色散X射线方法，振动样品磁强法和热重分析对新制备的纳米颗粒的结构进行了表征。这些纳米颗粒被确定为一锅三组分合成4,8-二氢吡喃[3,2- b]的有效催化剂] pyran衍生物，产率极高。容易通过磁倾析分离催化剂，并且将回收的纳米颗粒重新用于四个新的运行，而催化活性没有任何显着损失。评价了合成的二氢吡喃并[3,2- b ]吡喃的抗氧化和抗真菌活性，发现它们相对活性。
• Ultrasound promoted one-pot synthesis of 2-amino-4,8-dihydropyrano[3,2-b]pyran-3-carbonitrile scaffolds in aqueous media: A complementary ‘green chemistry’ tool to organic synthesis
  作者：Sayed Hossein Banitaba、Javad Safari、Shiva Dehghan Khalili

  DOI：10.1016/j.ultsonch.2012.07.007

  日期：2013.1

  A green and simple approach to assembling of 2-amino-4,8-dihydropyrano[3,2-b]pyran-3-carbonitrile scaffolds via three-component reaction of kojic acid, malononitrile, and aromatic aldehydes in aqueous media under ultrasound irradiation is described. The combinatorial synthesis was achieved for this methodology with applying ultrasound irradiation while making use of water as green solvent. In comparison to conventional methods, experimental simplicity, good functional group tolerance, excellent yields, short routine, and selectivity without the need for a transition metal or base catalyst are prominent features of this green procedure. (C) 2012 Elsevier B.V. All rights reserved.