6-amino-2,4-dihydro-4-(naphthalen-2-yl)-3-methylpyrano[2,3-c]pyrazole-5-carbonitrile

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-amino-2,4-dihydro-4-(naphthalen-2-yl)-3-methylpyrano[2,3-c]pyrazole-5-carbonitrile
• 英文别名: 6-amino-3-methyl-4-(naphthalen-2-yl)-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile；6-amino-3-methyl-4-naphthalen-2-yl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
• 化学式: C₁₈H₁₄N₄O
• 分子量: 302.335
• InChiKey: AYCZAKJQRAVLNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  87.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-萘甲醛 、 碘代醋酸乙酯 、 丙二腈 在 1-(carboxymethyl)pyridinium iodide 、 一水合肼 作用下， 以 neat (no solvent) 为溶剂， 反应 0.05h， 以83%的产率得到6-amino-2,4-dihydro-4-(naphthalen-2-yl)-3-methylpyrano[2,3-c]pyrazole-5-carbonitrile
  参考文献：
  名称：

  Catalytic application of 1-(carboxymethyl)pyridinium iodide on the synthesis of pyranopyrazole derivatives

  摘要：

  In this investigation, acetic acid functionalized pyridinium salt, namely 1-(carboxymethyl)pyridinium iodide {[cmpy]I}, has been introduced as reusable catalyst for green, simple and efficient synthesis of 6-amino-4-(4-methoxypheny1)-5-cyano-3-methyl-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazoles by the one-pot tandem four-component condensation reaction of aryl aldehydes with ethyl acetoacetate, malononitrile and hydrazine hydrate at 100 degrees C under solvent-free conditions. Additionally, H-1 and C-13 NMR, mass, CHN analysis, Fourier transform infrared spectroscopy (FT-IR), scanning electron microscope (SEM), thermal gravimetric analysis (TGA), differential thermal gravimetric (DTG), X-ray diffraction analysis (XRD), and calculation of crystallite size and inter planer distance of the catalyst have been investigated. (C) 2016 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2016.02.003

文献信息

• Synthesis of pyrano[2,3-<i>c</i> ]pyrazole derivatives using Fe₃ O₄ @SiO₂ @piperidinium benzene-1,3-disulfonate (Fe₃ O₄ @SiO₂ nanoparticle-supported IL) as a novel, green and heterogeneous catalyst
  作者：Ramin Ghorbani-Vaghei、Jafar Mahmoodi、Azadeh Shahriari、Yaser Maghbooli

  DOI：10.1002/aoc.3816

  日期：2017.12

  A simple, green and efficient protocol for the one‐pot four‐component synthesis of pyrano[2,3‐c]pyrazole derivatives produced from reaction between aryl aldehydes, ethyl acetoacetate, malononitrile and hydrazine hydrate in the presence of nano magnetic piperidinium benzene‐1,3‐disulfonate was synthesized in water at 60 °C. The Fe3O4@SiO2 nanoparticle‐supported IL was designed and synthesized. The present

  一种简单，绿色，高效的方案，用于在纳米磁性哌啶苯存在下，芳基醛，乙酰乙酸乙酯，丙二腈和水合肼之间反应生成的吡喃并[2,3- c ]吡唑衍生物的一锅四组分合成方法。1,3-二磺酸盐是在60°C的水中合成的。设计并合成了Fe 3 O 4 @SiO 2纳米负载的IL。本发明方法具有反应清洁，反应时间短，收率高至优异，易于纯化，催化剂易于回收等优点。
• Copper‐catalyzed multicomponent green reaction approach: Synthesis of dihydropyrano [2,3‐c] pyrazoles and evaluation of their anti‐cancer activity
  作者：Venkata Hema Kumar、Ramana Tamminana

  DOI：10.1002/jhet.4555

  日期：2023.1

  A facile, efficient, and simple one-pot multi-component protocol for the synthesis of pyrano[2,3-c] pyrazoles has been developed using a cheap and readily available copper catalyst under moderate reaction conditions. Target products are obtained from aromatic aldehyde via Knoevenagel condensation and Michael addition reactions. Functional group tolerance and reaction mechanisms have also been examined

  在温和的反应条件下，使用廉价且容易获得的铜催化剂开发了一种用于合成吡喃并 [2,3-c] 吡唑的简便、高效且简单的一锅法多组分方案。目标产物由芳香醛经 Knoevenagel 缩合和 Michael 加成反应获得。该方法还研究了官能团耐受性和反应机制。此外，我们还评估了目标产品的抗癌活性，我们也尝试将此方法用于实用目的。
• Cu(<scp>ii</scp>) immobilized on poly(guanidine-sulfonamide)-functionalized Bentonite@MgFe₂O₄: a novel magnetic nanocatalyst for the synthesis of 1,4-dihydropyrano[2,3-<i>c</i>]pyrazole
  作者：Sedigheh Alavinia、Ramin Ghorbani-Vaghei、Ramin Ghiai、Alireza Gharehkhani

  DOI：10.1039/d3ra00049d

  日期：——

  In this paper, we aim at synthesizing a new nanocomposite material in which bentonite acts as a nucleation site for MgFe₂O₄nanoparticles precipitation in the attendance of an external magnetic field (MgFe₂O₄@Bentonite).

  本文旨在合成一种新型纳米复合材料（MgFe2O4@Bentonite），其中膨润土在外加磁场的作用下可作为 MgFe2O4 纳米粒子沉淀的成核场所。
• Aqueous TPGS-750-M-mediated synthesis of pyrano[2,3-c]-pyrazoles: a sustainable and efficient approach
  作者：Adnan Cetin、Mehmet Yasin Bayden

  DOI：10.1007/s11164-024-05280-y

  日期：——

  describes a green and efficient synthesis method for pyrano[2,3-c]-pyrazoles, employing DL-alpha-tocopherol methoxypolyethylene glycol succinate solution (TPGS-750-M) as a green and biodegradable surfactant in water. The utilization of water as a reaction medium and TPGS-750-M as a surfactant obviates the necessity for organic solvents, thereby enhancing the environmental sustainability of the synthesis. The

  该文章描述了一种吡喃并[2,3-c]-吡唑类化合物的绿色高效合成方法，采用DL-α-生育酚甲氧基聚乙二醇琥珀酸酯溶液（TPGS-750-M）作为绿色、可生物降解的表面活性剂在水中。利用水作为反应介质和TPGS-750-M作为表面活性剂消除了对有机溶剂的需求，从而提高了合成的环境可持续性。使用各种光谱技术（包括1 H-NMR、13 C-NMR 和质谱）对使用这种新方法合成的化合物进行了表征。 图形概要
• Cinnamomum tamala leaf extract-mediated green synthesis of Ag nanoparticles and their use in pyranopyrazles synthesis
  作者：Sneha Yadav、Jitender M. Khurana

  DOI：10.1016/s1872-2067(15)60853-1

  日期：2015.7

  A novel, biochemical, and eco-friendly method has been developed for the synthesis of Ag nanoparticles using an aqueous leaf extract of readily accessible Cinnamomum tamala as reducing and stabilizing agents. These Ag nanoparticles were used to catalyze the synthesis of pyranopyrazoles. The green nature and ease of recovery and reusability of the catalyst, together with high yields of products, make this protocol attractive and useful. (C) 2015, Dalian Institute of Chemical Physics, Chinese Academy of Sciences. Published by Elsevier B.V. All rights reserved.