methyl 6-amino-5-cyano-4-phenyl-2,4-dihydropyrano[2,3-c]pyrazole-3-carboxylate | 1400891-56-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl 6-amino-5-cyano-4-phenyl-2,4-dihydropyrano[2,3-c]pyrazole-3-carboxylate
• CAS: 1400891-56-6
• 化学式: C₁₅H₁₂N₄O₃
• 分子量: 296.285
• InChiKey: IESKQGWLGHDVPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  苯甲醛 、 丁炔二酸二甲酯 、 丙二腈 在 cerium(IV) oxide 、 一水合肼 作用下， 以 水 为溶剂， 反应 0.52h， 以85%的产率得到methyl 6-amino-5-cyano-4-phenyl-2,4-dihydropyrano[2,3-c]pyrazole-3-carboxylate
  参考文献：
  名称：

  Environmentally benign synthesis of methyl 6-amino-5-cyano-4-aryl-2,4-dihydropyrano[2,3-c]pyrazole-3-carboxylates using CeO₂ nanoparticles as a reusable and robust catalyst

  摘要：

  在这项工作中，我们报道了CeO2纳米颗粒的合成和表征，作为一种高效催化剂，用于在水性介质中通过一锅四组分缩合反应制备甲基6-氨基-5-氰基-4-芳基-2,4-二氢吡喃并[2,3-c]吡唑-3-羧酸酯。使用无危害的有机溶剂、易于回收的催化剂、与各种功能团的兼容性以及高产率的产品使该方案具有吸引力、绿色和经济的特点。

  DOI：

  10.1515/znb-2016-0119

文献信息

• A green and convenient approach for the synthesis of methyl 6-amino-5-cyano-4-aryl-2,4-dihydropyrano[2,3-c]pyrazole-3-carboxylates via a one-pot, multi-component reaction in water
  作者：Adeleh Moshtaghi Zonouz、Issa Eskandari、Hamid Reza Khavasi

  DOI：10.1016/j.tetlet.2012.08.010

  日期：2012.10

  A green and efficient one-pot, four-component synthesis of methyl 6-amino-5-cyano-4-aryl-2,4-dihydropyrano[2,3-c]pyrazole-3-carboxylates in water is described. The method is catalyst-free, atom-economical, and does not involve tedious work-up or purification affording the target compounds in good yields.

  描述了一种绿色高效的一锅四组分甲基6-氨基-5-氰基-4-芳基-2,4-二氢吡喃并[2,3 - c ]吡唑-3-羧酸酯的合成方法。该方法是无催化剂的，原子经济的，并且不涉及繁琐的后处理或纯化，从而以良好的收率提供了目标化合物。
• Preparation and characterization of hexamethylenetetramine‐functionalized magnetic nanoparticles and their application as novel catalyst for the synthesis of pyranopyrazole derivatives
  作者：Ramin Ghorbani‐Vaghei、Vida Izadkhah

  DOI：10.1002/aoc.4025

  日期：2018.2

  A new magnetic catalyst was prepared through the reaction of silanol groups, on the surface of silica‐coated Fe3O4 magnetic nanoparticles, with (3‐chloropropyl)triethoxysilane followed by hexamethylenetetramine and chlorosulfonic acid. The obtained magnetic catalyst was characterized using thermogravimetric analysis, vibrating sample magnetometry, scanning electron microscopy and energy‐dispersive

  通过在涂有二氧化硅的Fe 3 O 4磁性纳米粒子表面上的硅烷醇基与（3-氯丙基）三乙氧基硅烷，然后六亚甲基四胺和氯磺酸反应，制备了一种新的磁性催化剂。使用热重分析，振动样品磁力分析，扫描电子显微镜和能量分散X射线分析对获得的磁性催化剂进行表征。在吡喃并吡唑化合物的合成中对其催化活性进行了研究，结果表明该产物的收率高，反应时间短。
• Uncapped SnO2 quantum dot catalyzed cascade assembling of four components: a rapid and green approach to the pyrano[2,3-c]pyrazole and spiro-2-oxindole derivatives
  作者：Sanjay Paul、Koyel Pradhan、Sirshendu Ghosh、S.K. De、Asish R. Das

  DOI：10.1016/j.tet.2014.02.077

  日期：2014.9

  A new uncapped SnO2 quantum dots (QDs) catalyzed strategy for the synthesis of substituted pyrano [2,3-c]pyrazole and spiro-2-oxindole derivatives has been developed via a multicomponent one pot approach in aqueous medium. The reactions can be performed at low catalyst loadings with excellent functional group tolerance. This communication also reports a comparative study of the efficiency related to the catalytic activity of uncapped SnO2 QDs, oleic acid capped SnO2 QDs, and SnO2 nanoflower. Uncapped SnO2 QDs, capped SnO2 QDs, and SnO2 nanoflower were prepared by simple solvothermal method and characterized by XRD, FESEM, and TEM images. The easy recovery of the catalyst and high yield of the products make the protocol attractive, sustainable, and economic. The catalyst was reused for six cycles with almost unaltered catalytic activity. (C) 2014 Elsevier Ltd. All rights reserved.