2-amino-4-(4-cyanophenyl)-6-(hydroxymethyl)-8-oxo-4,8-dihydropyrano[3,2-b]pyran-3-carbonitrile | 1613234-41-5

• 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: 2-amino-4-(4-cyanophenyl)-6-(hydroxymethyl)-8-oxo-4,8-dihydropyrano[3,2-b]pyran-3-carbonitrile
• 英文别名: 2-amino-4-(4-cyanophenyl)-4,8-dihydro-6-(hydroxymethyl)-8-oxo-pyrano[3,2-b]pyran3-carbonitrile；2-Amino-4-(4-cyano-phenyl)-4,8-dihydro-6-(hydroxymethyl)-8-oxo-pyrano[3,2-b]pyran3-carbonitrile；2-amino-4-(4-cyanophenyl)-6-(hydroxymethyl)-8-oxo-4H-pyrano[3,2-b]pyran-3-carbonitrile
• CAS: 1613234-41-5
• 化学式: C₁₇H₁₁N₃O₄
• 分子量: 321.292
• InChiKey: MFCNMBUJWAPABG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  129
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  曲酸 、 2-[(4-氰基苯基)亚甲基]丙二腈 以 水 为溶剂， 以86%的产率得到2-amino-4-(4-cyanophenyl)-6-(hydroxymethyl)-8-oxo-4,8-dihydropyrano[3,2-b]pyran-3-carbonitrile
  参考文献：
  名称：

  微波辅助水介导的迈克尔加成反应，合成曲酸衍生物

  摘要：

  描述了在微波辐射下在水的存在下合成取代的曲酸衍生物的高效方法。该转化代表了从简单的起始原料合成曲酸衍生物的有效方法。

  DOI：

  10.1007/s11164-015-2419-1

文献信息

• Supramolecular catalysis by β-cyclodextrin for the synthesis of kojic acid derivatives in water
  作者：Evgeny A. Kataev、Mittapalli Ramana Reddy、Gangarpu Niranjan Reddy、Vemulapati Hanuman Reddy、Cirandur Suresh Reddy、Basi V. Subba Reddy

  DOI：10.1039/c5nj01902h

  日期：——

  An efficient and green method has been developed for the synthesis of kojic acid derivatives by employing 20 mol% β-cyclodextrin in aqueous media.

  已开发出一种高效且环保的方法，通过在水介质中使用20 mol% β-环糊精合成曲酸衍生物。
• 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。
• MCM-41-SO3H: an efficient, reusable, heterogeneous catalyst for the one-pot, three-component synthesis of pyrano[3,2-b]pyrans
  作者：Yaghoub Sarrafi、Ebrahim Mehrasbi、Seyyedeh Zohreh Mashalchi

  DOI：10.1007/s11164-015-2275-z

  日期：2021.4

  MCM-41-SO 3 H, ordered mesoporous silica material MCM-41 with covalently anchored sulfonic acid groups, was used as a solid acid catalyst for the convenient, efficient, and ‘green’ synthesis of 2-amino-6-(hydroxymethyl)-8-oxo-4-aryl-4,8-dihydropyrano[3,2- b ]pyrans via a one-pot, three-component reaction of 5-hydroxy-2-(hydroxymethyl)-4 H -pyran-4-one, aldehydes and malononitrile in aqueous media.

  MCM-41-SO 3 H，具有共价锚定磺酸基团的有序介孔二氧化硅材料 MCM-41，被用作固体酸催化剂，用于方便、高效和“绿色”合成 2-氨基-6-（羟甲基） -8-oxo-4-aryl-4,8-​​dihydropyrano[3,2- b]pyrans 通过 5-hydroxy-2-(hydroxymethyl)-4 H -pyran-4- 的一锅三组分反应一、水性介质中的醛和丙二腈。
• The first efficient biocatalytic route for the synthesis of Kojic acid derivatives in aqueous media
  作者：Kiran S. Dalal、Mangal A. Chaudhari、Dipak S. Dalal、Bhushan L. Chaudhari

  DOI：10.1016/j.catcom.2021.106289

  日期：2021.4

  The first efficient biocatalytic route for the synthesis of kojic acid derivatives was developed in presence of an enzyme. In this process, benzaldehydes, malononitrile and kojic acid were used as starting materials while lipase from Aspergillus niger was the promiscuous biocatalyst giving high conversion (82–95%) of kojic acid derivatives in aqueous medium. The probable enzymatic mechanism is proposed

  在酶存在下，开发了合成曲酸衍生物的第一个有效的生物催化途径。在此过程中，以苯甲醛，丙二腈和曲酸为起始原料，而来自黑曲霉的脂肪酶则是混杂的生物催化剂，可在水性介质中实现高曲酸衍生物的转化率（82-95％）。本文提出了可能的酶促机制。脂肪酶可以重复使用直到连续三个周期，而活性没有明显损失。这种有效的生物过程具有取代现有化学催化过程以生产防止色素沉着过度的杂环抗酪氨酸酶化合物的潜力。
• Green synthesis of pyrano [3,2-b]pyran derivatives using nano Si–Mg–fluorapatite catalyst and the evaluation of their antibacterial and antioxidant properties
  作者：Fardad Ostadsharif Memar、Leila Khazdooz、Amin Zarei、Alireza Abbaspourrad

  DOI：10.1007/s00044-020-02598-1

  日期：2020.10

  In this study, we synthesize 2-amino-4-alkyl/aryl-6-(hydroxymethyl)-8-oxopyrano[3,2-b] pyran-3-carbonitriles derivatives using a multicomponent reaction featuring aromatic or aliphatic aldehydes, kojic acid, and malononitrile catalyzed by nano fluoroapatite doped with Si and Mg (Si-Mg-FA). All reactions were carried out in EtOH as the solvent under reflux and green condition. The process demonstrates various advantages, including high yields, short reaction times, and simple workup. In addition, toxic organic solvent is not used, nor is chromatographic purification of products required. We characterized the synthesized compounds by Fourier transform infrared,(CNMR)-C-13, and(1)HNMR spectroscopies. Additionally, the antibacterial properties of the pyrano[3,2-b]pyran derivatives were evaluated by determining the minimum inhibitory concentration on two gram-positive and gram-negative bacteria using the macro dilution method and compared with Penicillin and Tetracycline at the same conditions. The 2-amino-4-(2,4-dichlorophenyl)-4,8-dihydro-6-(hydroxymethyl)-8-oxo-pyrano[3,2-b]pyran-3-carbonitrile and the 2-amino-4-hexyl-4,8-dihydro-6-(hydroxymethyl)-8-oxo-pyrano[3,2-b]pyran-3-carbonitrile show the best antibacterial activity with a MIC value of 62.5 mu g/ml againstStaphylococcus aureus(ATCC 25923). Moreover, the antioxidant properties of the pyrano[3,2-b] pyrans derivatives were evaluated. It is notable that pyrano[3,2-b] pyrans derivatives, synthesized with substituent groups on benzaldehyde such as-NO2, -COOCH3, -OMe show the best antioxidant activity measured by DPPH radical-scavenging method.