2-Amino-4-(3,5-dimethoxyphenyl)-6-(hydroxymethyl)-8-oxo-4,8-dihydropyrano[3,2-b]pyran-3-carbonitrile | 876709-87-4

• 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-(3,5-dimethoxyphenyl)-6-(hydroxymethyl)-8-oxo-4,8-dihydropyrano[3,2-b]pyran-3-carbonitrile
• 英文别名: 2-amino-4-(3,5-dimethoxyphenyl)-6-(hydroxymethyl)-8-oxo-4H-pyrano[3,2-b]pyran-3-carbonitrile
• CAS: 876709-87-4
• 化学式: C₁₈H₁₆N₂O₆
• 分子量: 356.335
• InChiKey: KDJWYZMOCUDNSM-UHFFFAOYSA-N

物化性质

• 沸点：
  706.5±60.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  124
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  曲酸 、 3,5-二甲氧基苯甲醛 、 丙二腈 在 nano-silica sulfuric acid 作用下， 以 水 为溶剂， 反应 0.5h， 以84%的产率得到2-Amino-4-(3,5-dimethoxyphenyl)-6-(hydroxymethyl)-8-oxo-4,8-dihydropyrano[3,2-b]pyran-3-carbonitrile
  参考文献：
  名称：

  SiO₂–OSO₃H Nanoparticles: An Efficient, Versatile and New Reagent for the One-Pot Synthesis of 2-Amino-8-Oxo-4,8-Dihydropyrano[3,2-b]Pyran-3-Carbonitrile Derivatives in Water, a Green Protocol

  摘要：

  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。

  DOI：

  10.3184/174751914x13866053657371

文献信息

• 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.
• 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。