2-amino-4-(5-hydroxy-3-methyl-1H-pyrazol-4-yl)-6-nitro-4H-chromene-3-carbonitrile | 1238575-99-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-amino-4-(5-hydroxy-3-methyl-1H-pyrazol-4-yl)-6-nitro-4H-chromene-3-carbonitrile
• 英文别名: 2-amino-6-nitro-4-(5-hydroxy-3-methyl-1H-pyrazol-4-yl)-4H-chromene-3-carbonitrile
• CAS: 1238575-99-9
• 化学式: C₁₄H₁₁N₅O₄
• 分子量: 313.272
• InChiKey: LNYAGACOWMJNOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.55
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  151.09
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  5-硝基水杨醛 、 3-甲基-2-吡唑啉-5-酮 、 丙二腈 在 水 、 sodium acetate 作用下， 以 neat (no solvent) 为溶剂， 反应 0.17h， 以92%的产率得到2-amino-4-(5-hydroxy-3-methyl-1H-pyrazol-4-yl)-6-nitro-4H-chromene-3-carbonitrile
  参考文献：
  名称：

  Solvent-free and ‘on-water’ multicomponent assembling of salicylaldehydes, malononitrile and 3-methyl-2-pyrazolin-5-one: A fast and efficient route to the 2-amino-4-(1H-pyrazol-4-yl)-4H-chromene scaffold

  摘要：

  摘要 在研磨过程中，在少量水的存在下，醋酸钠催化的多组分反应使水杨醛、氰基丙烷和3-甲基-2-吡唑啉-5-酮迅速（10分钟）高效地形成取代的2-氨基-4-(1H-吡唑-4-基)-4H-克罗梅烯，产率为90-96%。这种针对取代的2-氨基-4-(1H-吡唑-4-基)-4H-克罗梅烯的快速有效的方法，作为治疗人类炎症性TNFα介导的疾病和不同生物医学应用的有前景的小分子配体，从多样性导向的大规模工艺的角度来看是有益的，代表了一种快速、高效和环保的多组分反应合成概念。

  DOI：

  10.1016/j.crci.2013.08.002

文献信息

• Synergetic effects of naturally sourced metal oxides in organic synthesis: a greener approach for the synthesis of pyrano[2,3-c]pyrazoles and pyrazolyl-4H-chromenes
  作者：Sachin K. Shinde、Megha U. Patil、Shashikant A. Damate、Suresh S. Patil

  DOI：10.1007/s11164-017-3197-8

  日期：2018.3

  A clean and more economic protocol for the synthesis of pyrano[2,3-c]pyrazoles and pyrazolyl-4H-chromenes has been carried out using bael fruit ash (BFA) as a non-conventional natural catalyst in aqueous condition at ambient temperature. The catalyst was obtained from renewable resources by simple thermal treatment to dry rind of Aegle marmelos (Bael) fruit and formation of its active phase was confirmed by AAS, DSC-TGA, XRD, FT-IR, and SEM techniques. The BFA catalyst was found to be a green, highly active, easily biodegradable, and recyclable without loss of activity after the fifth run. The methodology provides an alternative platform to the conventional catalyzed process.

  一种清洁且更经济的合成吡喔[2,3-c]吡唑和吡唑基-4H-色烯的协议已通过使用番木瓜果灰（BFA）作为非常规天然催化剂，在常温下的水相条件下进行。该催化剂由可再生资源制得，通过简单的热处理干燥Aegle marmelos（番木瓜）果皮，活性相的形成通过AAS、DSC-TGA、XRD、FT-IR和SEM技术得到了确认。实验结果表明，BFA催化剂是一种绿色、高活性、易降解且可回收的催化剂，在第五次反应后未出现活性丧失。这种方法为传统催化过程提供了替代平台。
• Four-component catalyst-free reaction in water: Combinatorial library synthesis of novel 2-amino-4-(5-hydroxy-3-methyl-1H-pyrazol-4-yl)-4H-chromene-3-carbonitrile derivatives
  作者：Kandhasamy Kumaravel、Gnanasambandam Vasuki

  DOI：10.1039/b913838b

  日期：——

  A catalyst-free combinatorial library of novel 2-amino-4-(5-hydroxy-3-methyl-1H-pyrazol-4-yl)-4H-chromene-3-carbonitrile derivatives has been developed by a four-component reaction between hydrazine hydrate (1), ethyl acetoacetate (2), 2-hydroxybenzaldehydes (3) and malononitrile (4) in water at ambient temperature.

  新型 2-氨基-4-(5-羟基-3-甲基-1H-吡唑-4-基)-4H-色烯-3-甲腈衍生物的无催化剂组合库是通过水合肼 (1)、乙酰乙酸乙酯 (2)、2-羟基苯甲醛 (3) 和丙二腈 (4) 在常温水中的四组分反应而开发的。
• Solvent-free and ‘on-water’ multicomponent assembling of salicylaldehydes, malononitrile and 3-methyl-2-pyrazolin-5-one: A fast and efficient route to the 2-amino-4-(1H-pyrazol-4-yl)-4H-chromene scaffold
  作者：Michail N. Elinson、Ruslan F. Nasybullin、Fedor V. Ryzhkov、Mikhail P. Egorov

  DOI：10.1016/j.crci.2013.08.002

  日期：2014.5

  Résumé Sodium acetate-catalyzed multicomponent reaction of salicylaldehydes, malononitrile and 3-methyl-2-pyrazolin-5-one initiated by grinding in mortar in the presence of small quantities of water results in the fast (10 min) and efficient formation of substituted 2-amino-4-(1H-pyrazol-4-yl)-4H-chromenes in 90–96% yields. The developed fast and efficient approach to the substituted 2-amino-4-(1H-pyrazol-4-yl)-4H-chromenes – the promising small-molecule ligands for the treatment of human inflammatory TNFα-mediated diseases and different biomedical applications –, is beneficial from the viewpoint of diversity-oriented large-scale processes and represents fast, efficient and environmentally benign synthetic concept for multicomponent reactions strategy.

  摘要 在研磨过程中，在少量水的存在下，醋酸钠催化的多组分反应使水杨醛、氰基丙烷和3-甲基-2-吡唑啉-5-酮迅速（10分钟）高效地形成取代的2-氨基-4-(1H-吡唑-4-基)-4H-克罗梅烯，产率为90-96%。这种针对取代的2-氨基-4-(1H-吡唑-4-基)-4H-克罗梅烯的快速有效的方法，作为治疗人类炎症性TNFα介导的疾病和不同生物医学应用的有前景的小分子配体，从多样性导向的大规模工艺的角度来看是有益的，代表了一种快速、高效和环保的多组分反应合成概念。