2-amino-3-cyano-4-(3,4-dimethoxyphenyl)-7-methyl-4H,5H-pyrano[3,2-c]pyran-5-one

• 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-3-cyano-4-(3,4-dimethoxyphenyl)-7-methyl-4H,5H-pyrano[3,2-c]pyran-5-one
• 英文别名: 2-amino-4-(3,4-dimethoxyphenyl)-7-methyl-5-oxo-4H,5H-pyrano[4,3-b]pyran-3-carbonitrile；2-amino-4-(3,4-dimethoxyphenyl)-7-methyl-5-oxo-4H-pyrano[3,2-c]pyran-3-carbonitrile
• 化学式: C₁₈H₁₆N₂O₅
• 分子量: 340.335
• InChiKey: XWFJZLMEJWQODW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-amino-3-cyano-4-(3,4-dimethoxyphenyl)-7-methyl-4H,5H-pyrano[3,2-c]pyran-5-one 、 乙酸酐 在 吡啶 作用下， 反应 7.0h， 以71%的产率得到2-(4-(3,4-dimethoxyphenyl)-7-methyl-5-oxo-3,4-dihydropyrano[3,4-e][1,3]oxazin-2(5H)-ylidene)-3-oxobutanenitrile
  参考文献：
  名称：

  C-C 键的易断裂：吡喃衍生物转化为 1,3-恶嗪衍生物

  摘要：

  已经发现了涉及独特的 C-C 键断裂的级联反应。该协议为在温和条件下合成 1,3-恶嗪衍生物提供了一种不寻常且简便的方法。

  DOI：

  10.1016/j.tet.2012.05.089
• 作为产物：
  描述：

  4-羟基-6-甲基-2-吡喃酮 、 ((3,4-二甲氧基苯基)亚甲基)甲烷-1,1-二甲腈 在 苄基三乙基氯化铵 作用下， 以 水 为溶剂， 反应 10.0h， 以91%的产率得到2-amino-3-cyano-4-(3,4-dimethoxyphenyl)-7-methyl-4H,5H-pyrano[3,2-c]pyran-5-one
  参考文献：
  名称：

  Shi, Da-Qing; Niu, Li-Hui; Wang, Xiang-Shan, Journal of Chemical Research, 2005, # 11, p. 724 - 726

  摘要：

  DOI：

文献信息

• 4-(Succinimido)-1-butane sulfonic acid as a Brönsted acid catalyst for the synthesis of pyrano[4,3-b]pyran derivatives using thermal and ultrasonic irradiation
  作者：Nader Ghaffari Khaligh、Sharifah Bee Abd Hamid

  DOI：10.1016/s1872-2067(14)60307-7

  日期：2015.5

  Abstract 4-(Succinimido)-1-butane sulfonic acid was shown to be an efficient and reusable Bronsted acid catalyst for the synthesis of pyrano[4,3- b ]pyran derivatives using thermal and ultrasonic conditions. The catalyst was prepared by mixing succinimide and 1,4-butanesultone, which is simpler and safer than the preparation of succinimide sulfonic acid. This method has the advantages of high yield

  摘要 4-(琥珀酰亚胺)-1-丁烷磺酸被证明是一种高效且可重复使用的布朗斯台德酸催化剂，可用于在热和超声条件下合成吡喃并[4,3-b]吡喃衍生物。该催化剂由琥珀酰亚胺和1,4-丁烷磺内酯混合制备，比制备琥珀酰亚胺磺酸更简单、更安全。该方法具有收率高、反应清洁、方法简单、反应时间短等优点。催化剂可以循环使用而不会损失活性。
• 1H-imidazol-3-ium tricyanomethanide {[HIM]C(CN)3} as a nanostructured molten salt catalyst: application to the synthesis of pyrano[4,3‐b]pyrans
  作者：Mohammad Ali Zolfigol、Meysam Yarie、Saeed Baghery、Abbas Khoshnood、Diego A. Alonso

  DOI：10.1007/s11164-016-2826-y

  日期：2017.5

  Additionally, the catalytic activity of [HIMI]C(CN)3} (1, 2 mol%) has been tested in a three-component domino Knoevenagel condensation reaction. A range of structurally diverse aromatic aldehydes (2a–p), malononitrile (3), and 4‐hydroxy‐6‐methyl‐2 H ‐pyran‐2‐one (4) are tolerated for the synthesis of 2-amino-7-methyl-5-oxo-4-aryl-4,5-dihydropyrano[4,3-b]pyran-3-carbonitrile derivatives (5a–p) under neat conditions

  在这项工作中，我们已经合成了一种新型的纳米结构熔融盐1 H-咪唑-3-三氰基甲磺酸[HIMI] C（CN）3 }（1），作为一种高效且绿色协议兼容的催化剂。这种新的熔融盐已通过多种分析技术进行了全面表征，例如FT-IR，1 HNMR，13 CNMR，热重分析，导数热重分析，差热分析，X射线衍射，扫描电子显微镜和分辨率透射电镜。此外，[HIMI] C（CN）3的催化活性}（1，2 mol％）已在三组分多米诺Knoevenagel缩合反应中进行了测试。可以耐受一系列结构多样的芳族醛（2a-p），丙二腈（3）和4-羟基-6-甲基-2 H- 吡喃-2-酮（4）来合成2-氨基-7-甲基-5-氧代-4-芳基-4,5-二氢吡喃[4,3-b]吡喃-3-腈衍生物（5a–p）在纯净条件下于50°C进行。所得结果表明，催化剂1显示出令人感兴趣的催化性能，例如干净的反应曲线，成本效益和绿色条件。重要的是，上述
• 4-(Succinimido)-1-butane sulfonic acid as a Brönsted acid catalyst for synthesis of pyrano[4,3-b]pyran derivatives under solvent-free conditions
  作者：Nader Ghaffari Khaligh

  DOI：10.1016/j.cclet.2014.10.009

  日期：2015.1

  4-(Succinimido)-1-butane sulfonic acid as an efficient and reusable Bronsted acid catalyzed the synthesis of pyrano[4,3-b]pyran derivatives under solvent-free conditions. The catalyst can be prepared by mixing succinimide and 1,4-butanesultone that is more simple and safer than the preparation of succinimide sulfonic acid. This method has the advantages of high yield, clean reaction, simple methodology and short reaction time. The catalyst could be recycled without significant loss of activity. (C) 2014 Nader Ghaffari Khaligh. Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. All rights reserved.
• Nickel Nanoparticles as Semiheterogeneous Catalyst for One-Pot, Three-Component Synthesis of 2-Amino-4<i>H</i>-pyrans and Pyran Annulated Heterocyclic Moieties
  作者：Jitender M. Khurana、Kanika Vij

  DOI：10.1080/00397911.2012.700474

  日期：2013.9.2

  An efficient route for the synthesis of 2-amino-4H-pyrans and pyran annulated heterocyclic moieties has been reported via one-pot tandem Knoevenagel-cyclocondensation of aldehydes, malononitrile, and carbocyclic/heterocyclic 1,3-diones in the presence of stabilized nickel nanoparticles in ethylene glycol at room temperature. A wide range of aromatic aldehydes undergo the condensation readily to afford the pharmacologically important compounds in excellent yields. Bis-pyranization has been observed in the reactions of terephthaldehyde. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.
• Alum [KAl(SO4)2·12H2O]: a green and efficient catalyst for synthesis of pyrano[4,3-b]pyrans in water under conventional and microwave conditions
  作者：Deepika Rajguru、Balwant S. Keshwal、Shubha Jain、Vasant W. Bhagwat

  DOI：10.1007/s00706-013-0975-x

  日期：2013.9

  One-pot synthesis of pyrano[4,3-b]pyrans by condensation of 4-hydroxy-6-methylpyran-2-one, aromatic aldehydes, and malononitrile or cyanoacetates in water using alum as a non-toxic, readily available, and reusable catalyst at 80 A degrees C under conventional conditions and also under microwave irradiation is described.