2-amino-4-(3-nitrophenyl)-6-phenylnicotinonitrile | 331962-47-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-amino-4-(3-nitrophenyl)-6-phenylnicotinonitrile
• 英文别名: 2-amino-4-(3-nitrophenyl)-6-phenylpyridine-3-carbonitrile
• CAS: 331962-47-1
• 化学式: C₁₈H₁₂N₄O₂
• 分子量: 316.319
• InChiKey: FYOGSLKDQZZTGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-amino-4-(3-nitrophenyl)-6-phenylnicotinonitrile 在 palladium on activated charcoal 吡啶 、 sodium hydroxide 、 氢气 作用下， 以 甲醇 、 乙酸乙酯 、 乙腈 为溶剂， 生成 Sodium; 4-[3-(2-amino-3-cyano-6-phenyl-pyridin-4-yl)-phenylcarbamoyl]-4-hydroxy-butyrate
  参考文献：
  名称：

  Discovery of novel and selective IKK-β serine-threonine protein kinase inhibitors. Part 1

  摘要：

  IkappaB kinase beta (IKK-beta) is a serine-threonine protein kinase critically involved in the activation of the transcription factor Nuclear Factor kappa B (NF-kappaB) in response to various inflammatory stimuli. We have identified a small molecule inhibitor of IKK-beta. Optimization of the lead compound resulted in improvements in both in vitro and in vivo potency, and provided IKK-beta inhibitors exhibiting potent activity in an acute cytokine release model (LPS-induced TNFalpha). (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)01046-6
• 作为产物：
  描述：

  3-硝基查耳酮 、 丙二腈 在 ammonium acetate 作用下， 以 乙醇 为溶剂， 以88%的产率得到2-amino-4-(3-nitrophenyl)-6-phenylnicotinonitrile
  参考文献：
  名称：

  Sulfonic Acid Supported Phosphonium Based Ionic Liquid Functionalized SBA-15 for the Synthesis of 2-Amino-3-cyano-4,6-diarylpyridines

  摘要：

  DOI：

  10.1080/15533174.2014.988234

文献信息

• The green synthesis of 2-amino-3-cyanopyridines using SrFe12O19 magnetic nanoparticles as efficient catalyst and their application in complexation with Hg2+ ions
  作者：Zohreh kheilkordi、Ghodsi Mohammadi Ziarani、Shahriyar Bahar、Alireza Badiei

  DOI：10.1007/s13738-018-1514-9

  日期：2019.2

  AbstractIn this paper, a family of 2-amino-4,6-diphenylnicotinonitriles are prepared from aromatic aldehydes, acetophenone derivatives, malononitrile, and ammonium acetate via one-pot reaction catalyzed by SrFe12O19 magnetic nanoparticles. SrFe12O19 was an efficient, green, and reusable nanomagnetic heterogeneous catalyst with the average particles’ size of 70 nm which can be recycled and readily and

  摘要本文通过SrFe 12 O 19磁性纳米粒子的一锅法反应，由芳族醛，苯乙酮衍生物，丙二腈和乙酸铵制备了2-氨基-4,6-二苯基烟腈。锶铁12 O 19是一种有效，绿色，可重复使用的纳米磁性非均相催化剂，平均粒径为70 nm，可以回收利用，并使用外部磁体将其与反应混合物分离。较短的反应时间和所需产物的高收率是本方法的主要优点。随后，采用分光光度法研究了2-氨基-4,6-二苯基烟腈作为有机配体与几种金属离子如Ag +，Cd 2 +，Co 2 +，Cr 3+，Cu 2的络合过程。+，Fe 3+，Hg 2 +，Mn 2 +，Ni 2 +，Pb 2+和Zn在25°C下于CH 3 CN溶液中添加2+。根据获得的结果，仅通过添加Hg 2+离子改变了CH 3 CN溶液中有机配体的吸收光谱，这表明在有机配体和Hg 2+离子之间形成了一种吸收性配位化合物。通过计算机拟合不同摩尔比的摩尔吸光度测量值，计算出所得配合物的化学计量。
• Experimental and theoretical studies of the nanostructured {Fe₃O₄@SiO₂@(CH₂)₃Im}C(CN)₃catalyst for 2-amino-3-cyanopyridine preparation<i>via</i>an anomeric based oxidation
  作者：Mohammad Ali Zolfigol、Mahya Kiafar、Meysam Yarie、Avat(Arman) Taherpour、Mahdi Saeidi-Rad

  DOI：10.1039/c6ra12299j

  日期：——

  2-Amino-4,6-diphenylnicotinonitriles were prepared by using Fe3O4@SiO2@(CH2)3Im}C(CN)3 as a nanostructured catalyst with an ionic liquid tag under solvent free and benign conditions. Experimental evidence and theoretical studies confirmed that the final step of the synthetic pathway proceeded via an anomeric based oxidation mechanism. A good range of aromatic aldehydes were condensed with acetophenone

  以Fe 3 O 4 @SiO 2 @（CH 2）3 Im} C（CN）3作为具有离子液体标签的纳米结构催化剂，在无溶剂和良性条件下，制备了2-氨基-4,6-二苯基烟腈。实验证据和理论研究证实，合成途径的最后一步是通过基于异头物的氧化机理进行的。一系列芳香醛与苯乙酮衍生物，丙二腈和乙酸铵缩合，从而在较短的反应时间内即可获得相应的产物，并且产率高至高。
• Fe₃O₄@TiO₂@O₂PO₂(CH₂)NHSO₃H as a novel nanomagnetic catalyst: Application to the preparation of 2-amino-4,6-diphenylnicotinonitriles via anomeric-based oxidation
  作者：Mohammad Ali Zolfigol、Meysam Yarie

  DOI：10.1002/aoc.3598

  日期：2017.5

  A new, green and reusable nanomagnetic heterogeneous catalyst, namely Fe3O4@TiO2@O2PO2(CH2)NHSO3H, was synthesized and fully characterized using suitable techniques such as infrared spectroscopy, X‐ray diffraction, scanning and transmission electron microscopies, thermogravimetry, vibrating sample magnetometry and energy‐dispersive X‐ray spectroscopy. The applicability of the constructed heterogeneous

  一种新型的绿色可重复使用的纳米磁性非均相催化剂，即Fe 3 O 4 @TiO 2 @O 2 PO 2（CH 2）NHSO 3使用合适的技术合成和完全表征了H，例如红外光谱，X射线衍射，扫描和透射电子显微镜，热重分析，振动样品磁力分析和能量分散X射线光谱。在多种芳族醛，苯乙酮衍生物，丙二腈和乙酸铵的反应下，成功地探索了构造的异质核-壳催化剂作为促进剂的适用性，用于合成2-氨基-4,6-二苯基烟腈衍生物。在无溶剂条件下，以较短的反应时间以高到高的产率获得了所需的产物。在合成途径的最后一步，建议的机理为产物提供了基于异头的氧化途径。
• A concise route for the one-pot multi-component synthesis of 4,6-disubstituted 2-aminopyridine-3-carbonitriles and pyranopyrazoles using cobalt (II) nitrate hexahydrate as catalyst
  作者：Hamed PEJMAN、Nourallah HAZERI、Maryam FATAHPOUR、Homayoun FAROUGHI NIYA

  DOI：10.33224/rrch/2019.64.3.05

  日期：——

  Three facile and efficient routes for one-pot, cobalt (II) nitrate hexahydrate catalyzed multi-component synthesis of 2-amino-3cyanopyridine and pyranopyrazole derivatives have been developed. The present protocols offer the products in good yields from the simple and readily available starting materials. The other salient features of these protocols are operational simplicity, easy isolation of product

  已经开发了三种简便有效的途径，用于一锅硝酸钴（II）六水合物催化的2-氨基-3氰基吡啶和吡喃并吡咯衍生物的多组分合成。本方案从简单易得的起始原料中以高收率提供产物。这些方案的其他显着特征是操作简便，无需柱色谱纯化即可轻松分离产物，以及使用六水合硝酸钴（II）作为有效催化剂。
• Synthesis, characterization, and application of CoFe2O4@TRIS@sulfated boric acid nanocatalyst for the synthesis of 2-amino-3-cyanopyridine derivatives
  作者：Homayoun Faroughi Niya、Nourallah Hazeri、Malek Taher Maghsoodlou、Maryam Fatahpour

  DOI：10.1007/s11164-020-04369-4

  日期：2021.4

  this research is the synthesis of a novel acidic nanocatalyst using the layer-by-layer assembly technique. The CoFe2O4@TRIS@sulfated boric acid nanoparticles were easily synthesized and studied as a highly beneficial, recyclable, and magnetite nanocatalyst for the synthesis of 2-amino-3-cyanopyridine derivatives. The chemical structure of CoFe2O4@TRIS @sulfated boric acid nanocatalyst was completely confirmed

  摘要 这项研究的目的是使用逐层组装技术合成新型酸性纳米催化剂。CoFe 2 O 4 @ TRIS @硫酸化的硼酸纳米颗粒易于合成，并作为合成2-氨基-3-氰基吡啶衍生物的高度有益，可回收的磁铁矿纳米催化剂进行了研究。用FeSEM，Map，EDS，XRD，TGA / DTG，VSM和FT-IR分析等不同技术完全证实了CoFe 2 O 4 @ TRIS @硫酸化硼酸纳米催化剂的化学结构。简而言之，新合成的纳米催化剂具有一些优点，例如后处理简单，高度稳定，对环境友好，可重复使用，产率高以及反应时间短。 图形摘要