methyl 6-amino-5-cyano-2,4-dihydro-4-(3-nitrophenyl)pyrano[2,3-c]pyrazole-3-carboxylate | 1400891-62-4

• 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: methyl 6-amino-5-cyano-2,4-dihydro-4-(3-nitrophenyl)pyrano[2,3-c]pyrazole-3-carboxylate
• 英文别名: methyl 6-amino-5-cyano-4-(3-nitrophenyl)-2,4-dihydropyrano[2,3-c]pyrazole-3-carboxylate
• CAS: 1400891-62-4
• 化学式: C₁₅H₁₁N₅O₅
• 分子量: 341.283
• InChiKey: ZAMKLHKOFZKDIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  160
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  间硝基苯甲醛 、 丁炔二酸二甲酯 、 丙二腈 在 一水合肼 作用下， 以 水 为溶剂， 反应 1.0h， 以66%的产率得到methyl 6-amino-5-cyano-2,4-dihydro-4-(3-nitrophenyl)pyrano[2,3-c]pyrazole-3-carboxylate
  参考文献：
  名称：

  一种绿色便捷的方法，可通过单罐多组分反应合成6-氨基5-氰基-4-氰基-4-芳基-2,4-二氢吡喃并[2,3 - c ]吡唑-3-羧酸甲酯水

  摘要：

  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。

  DOI：

  10.1016/j.tetlet.2012.08.010

文献信息

• Environmentally benign synthesis of methyl 6-amino-5-cyano-4-aryl-2,4-dihydropyrano[2,3-<i>c</i>]pyrazole-3-carboxylates using CeO₂ nanoparticles as a reusable and robust catalyst
  作者：Javad Safaei-Ghomi、Mehrnoosh Asgari-Kheirabadi、Hossein Shahbazi-Alavi

  DOI：10.1515/znb-2016-0119

  日期：2016.11.1

  In this work, we report the synthesis and characterization of CeO₂ nanoparticles as an efficient catalyst for the preparation of methyl 6-amino-5-cyano-4-aryl-2,4-dihydropyrano[2,3-c]pyrazole-3-carboxylates via one-pot four-component condensation reaction of dimethyl acetylenedicarboxylate, hydrazine hydrate, malononitrile, and aldehydes in aqueous medium. The use of a non-hazardous organic solvent, easy recovery of the catalyst, compatibility with various functional groups, and high yield of the products make the protocol attractive, greener, and economic.

  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。
• 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.