6-amino-3,4-dimethyl-4-(4-methylphenyl)-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile | 1235990-60-9

• 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: 6-amino-3,4-dimethyl-4-(4-methylphenyl)-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
• 英文别名: 6-amino-2,4-dihydro-3,4-dimethyl-4-p-tolylpyrano[2,3-c]pyrazole-5-carbonitrile
• CAS: 1235990-60-9
• 化学式: C₁₆H₁₆N₄O
• 分子量: 280.329
• InChiKey: BFTLXRLPRRLJGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.42
• 重原子数：
  21.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  87.72
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  乙酰乙酸乙酯 、 对甲基苯乙酮 、 丙二腈 在 一水合肼 、 全氨基倍他环糊精 作用下， 反应 0.02h， 以99%的产率得到6-amino-3,4-dimethyl-4-(4-methylphenyl)-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
  参考文献：
  名称：

  Solvent-free multicomponent synthesis of pyranopyrazoles: per-6-amino-β-cyclodextrin as a remarkable catalyst and host

  摘要：

  A simple, green and efficient protocol is developed with per-6-amino-beta-cyclodextrin (per-6-ABCD) which acts simultaneously as a supramolecular host and as an efficient solid base catalyst for the solvent-free syntheses of various dihydropyrano[2,3-c]pyrazole derivatives involving a four-component reaction. This atom-economical protocol, reported for the first time with ketones also, includes a much milder procedure, does not involve any tedious work-up or purification, avoids hazardous reagents/byproducts and results in near quantitative yields. The catalyst can be reused at least six times without any change in its catalytic activity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.04.087

文献信息

• Supported palladium oxide nanoparticles in Al-SBA-15 as an efficient and reusable catalyst for the synthesis of pyranopyrazole and benzylpyrazolyl coumarin derivatives via multicomponent reactions
  作者：Majid M. Heravi、Reihaneh Malakooti、Kosar Kafshdarzadeh、Zahra Amiri、Vahideh Zadsirjan、Hassan Atashin

  DOI：10.1007/s11164-021-04619-z

  日期：2022.1

  An eco-friendly method for diversity-oriented synthesis of substituted dihydropyrano[2,3-c]pyrazole and benzylpyrazolyl coumarin derivatives has been achieved via one-pot and multicomponent reaction in the presence of PdO/Al-SBA-15 as an efficient and recyclable catalyst in H2O/EtOH under reflux conditions. The significant merits of this method are wide scope, high yields of the desired products, short

  在 PdO/Al-SBA-15 存在下，通过一锅多组分反应，实现了一种生态友好的方法，用于合成取代二氢吡喃并[2,3- c ]吡唑和苄基吡唑基香豆素衍生物，作为一种高效且回流条件下在 H 2 O/EtOH 中的可回收催化剂。该方法的显着优点是适用范围广、所需产物收率高、反应时间短和后处理程序简单。此外，这种纳米催化剂被简单地回收和重复使用五次，而催化活性和性能没有显着损失。 图形概要
• Facile synthesis of pyranopyrazoles and 3,4-dihydropyrimidin-2(1H)-ones by a Ti-grafted polyamidoamine dendritic silica hybrid catalyst via a dual activation route
  作者：P. S. Sinija、K. Sreekumar

  DOI：10.1039/c5ra16723j

  日期：——

  preparation of biologically potent pyranopyrazoles and 3,4-dihydropyrimidin-2(1H)-ones are described here. A Ti-grafted polyamidoamine dendritic silica hybrid catalyst was successfully synthesized, and its catalytic performance was studied in two important multicomponent reactions such as Biginelli reaction and pyranopyrazole synthesis. Studies demonstrate that the crystalline pore wall structure of the dendritic

  一种简单，高效且环保的方法，可制备具有生物活性的吡喃并吡唑和3,4-二氢嘧啶-2（1 H）-此处描述了一个。成功合成了钛接枝的聚酰胺型胺型树枝状二氧化硅杂化催化剂，并在Biginelli反应和吡喃并吡咯合成等两个重要的多组分反应中研究了其催化性能。研究表明，树枝状二氧化硅杂化催化剂的结晶孔壁结构使反应物易于吸附。二氧化硅表面的路易斯酸性和路易斯碱性相结合，有助于并加速高产率合成所需产物。本方法的关键优点是产物的优异产率，低催化剂负载，较短的反应时间，容易的后处理以及通过非色谱法纯化产物和催化剂的可重复使用性。
• Bovine serum albumin catalyzed one-pot, three-component synthesis of dihydropyrano[2,3-c]pyrazole derivatives in aqueous ethanol
  作者：Kiran S. Dalal、Yogesh A. Tayade、Yogesh B. Wagh、Darshak R. Trivedi、Dipak S. Dalal、Bhushan L. Chaudhari

  DOI：10.1039/c5ra13014j

  日期：——

  (BSA) catalyzed synthesis of dihydropyrano[2,3-c]pyrazole derivatives via a one pot, three component reaction of an aldehyde/ketone/isatin, malononitrile and 3-methyl-1H-pyrazol-5-(4H)-one in H2O–EtOH (7 : 3) at ambient temperature was developed in this work. The catalyst was found to work efficiently for aldehydes, ketones and isatins to give the corresponding dihydropyrano[2,3-c]pyrazole and spiro[indoline-3

  牛血清白蛋白（BSA）通过一锅，醛/酮/ Isatin，丙二腈和3-甲基-1 H-吡唑-5-（4）的三组分反应催化合成二氢吡喃并[2,3- c ]吡唑衍生物在这项工作中，在环境温度下在H 2 O–EtOH（7：3）中形成了H）-1。发现该催化剂可有效地用于醛，酮和靛红，得到相应的二氢吡喃并[2,3- c ]吡唑和螺[吲哚啉-3,4'-吡喃并[2,3- c][吡唑]衍生物的收率很高。BSA对各种醛，芳族/脂肪族酮和取代的isatins表现出广泛的催化混杂性。使用对环境无害的方案，催化剂的可重复使用性，避免使用有害溶剂，优异的收率，易于加工且不会形成副产物，使得BSA成为进一步用作生物催化剂的有吸引力的候选者。
• Multicomponent synthesis of dihydropyrano[2,3-c]pyrazoles catalyzed by lipase from Aspergillus niger
  作者：Pranjal P. Bora、Manisha Bihani、Ghanashyam Bez

  DOI：10.1016/j.molcatb.2013.03.015

  日期：2013.8

  Lipase from Aspergillus niger (ANL) was found to be an extremely effective catalyst for four-component synthesis of dihydropyrano[2,3-c]pyrazoles from a stoichiometric mixture of ethyl acetoacetate, hydrazine hydrate, aldehyde/ketone, and malononitrile in ethanol. The lipase ANL showed a broad range of enzymatic promiscuity toward various aromatic and aliphatic aldehydes as well as ketones. Use of environmentally benign biocatalyst, reusability of the catalyst, room temperature reaction conditions, no hazardous solvent, and excellent yields are some of the important features of this protocol. (C) 2013 Elsevier B.V. All rights reserved.