2-amino-3-cyano-6-(4-chlorophenyl)-4-(4-fluorophenyl)pyridine | 160031-97-0

• 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-3-cyano-6-(4-chlorophenyl)-4-(4-fluorophenyl)pyridine
• 英文别名: 2-amino-4-(4-fluorophenyl)-6-(4-chlorophenyl)nicotinonitrile；2-Amino-6-(4-chlorophenyl)-4-(4-fluorophenyl)pyridine-3-carbonitrile
• CAS: 160031-97-0
• 化学式: C₁₈H₁₁ClFN₃
• 分子量: 323.757
• InChiKey: IVTJKFRKCKNSHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 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：
  62.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-amino-3-cyano-6-(4-chlorophenyl)-4-(4-fluorophenyl)pyridine 在 氢氧化钾 作用下， 反应 22.0h， 生成 2-amino-6-(4-chlorophenyl)-4-(4-fluorophenyl)pyridine-3-carboxamide
  参考文献：
  名称：

  SYNTHESIS OF RIBONUCLEOSIDES OF 2-THIOXOPYRIDO [2,3-d]PYRIMIDINES BY PHASE TRANSFER CATALYSIS AND THEIR ANTIMICROBIAL ACTIVITY

  摘要：

  The ribonucleosides viz; 2-thioxo-3,5,7-trisubstituted-1-(2,3,5-tri-O-benzoyl-beta -D-ribofuranosyl)pyrido[2,3-d]pyrimidine-4 (1H)-ones have been synthesized via phase transfer ribosylation of 2-thioxo- 3,5,7-trisubstituted pyrido[2,3-d]pyrimidine-4(IH)-ones with 2,3,5-tri-O-benzoyl-beta -D- ribofuranosyl bromide in biphasic solvent such as CH2Cl2-50% aqueous NaOH using tetrabutylammonium bromide as phase transfer catalysis (PTC). The synthesized compounds have been characterized by elemental analyses, spectral data and screened for their antimicrobial activity.

  DOI：

  10.1080/10426509808033729
• 作为产物：
  描述：

  3-(4-chlorophenyl)-1-(4-fluorophenyl)prop-2-en-1-one 、 丙二腈 在 ammonium acetate 作用下， 以 乙醇 为溶剂， 反应 0.4h， 以86%的产率得到2-amino-3-cyano-6-(4-chlorophenyl)-4-(4-fluorophenyl)pyridine
  参考文献：
  名称：

  'One Pot' Synthesis of 2-Amino-3-cyano-4,6-diarylpyridines under Ultrasonic Irradiation and Grindstone Technology

  摘要：

  在超声波照射和磨石技术条件下，通过查尔酮、丙二腈和醋酸铵的三组分反应，简单方便地 "一锅 "合成了 2-氨基-3-氰基-4,6-二芳基吡啶衍生物。根据元素分析和光谱数据（IR、$^1H$ NMR、$^{13}C$ NMR 和质量）对所有合成化合物进行了表征。

  DOI：

  10.5012/bkcs.2010.31.11.3180

文献信息

• Aqueous media preparation of 2-amino-4,6-diphenylnicotinonitriles using cellulose sulfuric acid as an efficient catalyst
  作者：Syed Sheik Mansoor、Krishnamoorthy Aswin、Kuppan Logaiya、Prasanna Nithiya Sudhan、Saleem Malik

  DOI：10.1007/s11164-012-1008-9

  日期：2014.2

  es via four-component reaction of aromatic aldehydes, acetophenone derivatives, malononitrile and ammonium acetate is described. The reactions were done in water as solvent using cellulose sulfuric acid as catalyst. This simple protocol offer advantages such as shorter reaction times, simple work-up procedure, excellent yields and catalyst recovery.

  描述了一种通过芳族醛，苯乙酮衍生物，丙二腈和乙酸铵的四组分反应合成2-氨基-4,6-二苯基烟腈的简便方法。反应以纤维素硫酸为催化剂，在水为溶剂中进行。这种简单的方案具有诸如缩短反应时间，简化后处理程序，优异的收率和催化剂回收率等优点。
• One-pot synthesis of 2-amino-3-cyanopyridines and hexahydroquinolines using eggshell-based nano-magnetic solid acid catalyst via anomeric-based oxidation
  作者：Tahere Akbarpoor、Ardeshir Khazaei、Jaber Yousefi Seyf、Negin Sarmasti、Maryam Mahmoudiani Gilan

  DOI：10.1007/s11164-019-04049-y

  日期：2020.2

  In the present research, the eggshell as a hazardous waste by European Union regulations was converted to a valuable catalyst, namely nano-Fe3O4@(HSO4)2. The as-prepared catalyst, first, was characterized using different techniques, including Fourier-transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), energy-dispersive X-ray spectroscopy (EDX), field emission scanning electron microscopy (FESEM), and transmission electron microscopy (TEM). Back-titration method confirmed the loading of a high surface density of acidic group, namely 8.8 mmol HSO4 per gram of the catalyst. The catalytic property of the as-prepared catalyst was examined in the synthesis of 2-amino-3-cyanopyridines via anomeric-based oxidation (ABO), and hexahydroquinolines derivatives. High yield, short reaction time, solvent-free condition, waste to wealth, and optimization with the design of experiment are the major advantages of the present work. Taken together, these results suggest the conversion of waste to wealth products around the world and usage in organic transformation.

  在本项研究中，通过欧洲联盟法规界定为危险废物的蛋壳被转化为一种有价值的催化剂，即纳米Fe3O4@(HSO4)2。所制备的催化剂首先通过多种技术进行了表征，包括傅里叶变换红外光谱（FT-IR）、X射线衍射（XRD）、能量色散X射线光谱（EDX）、场发射扫描电子显微镜（FESEM）和透射电子显微镜（TEM）。反滴定法证实了催化剂表面存在高密度的酸性基团，具体为每克催化剂含有8.8 mmol HSO4。通过异头氧化（ABO）合成2-氨基-3-氰基吡啶以及六氢喹啉衍生物时，考察了所制备催化剂的催化性能。高产率、短反应时间、无溶剂条件、废物利用以及结合实验设计的优化是本工作的主要优势。综合来看，这些结果表明了废物在全球范围内的财富转化潜力，并可用于有机转化过程。
• Application of salicylic acid as an eco‐friendly and efficient catalyst for the synthesis of 2,4,6‐triaryl pyridine, 2‐amino‐3‐cyanopyridine, and polyhydroquinoline derivatives
  作者：Majid Roozifar、Nourallah Hazeri、Homayoun Faroughi Niya

  DOI：10.1002/jhet.4242

  日期：2021.5

  In this study, three eco‐friendly, efficient, and convenient protocols have been reported for one‐pot synthesis of 2,4,6‐triaryl pyridine, 2‐amino‐3‐cyanopyridine, and polyhydroquinoline derivatives using salicylic acid as a catalyst under solvent‐free condition. The reported protocols offer several significant advantages such as the application of a nontoxic, neutral, and cheap catalyst, environmentally

  在这项研究中，已经报道了使用水杨酸作为催化剂，在一个锅中合成2,4,6-三芳基吡啶，2-氨基-3-氰基吡啶和聚氢喹啉衍生物的三种环保，高效和便捷的方案。无溶剂条件。所报道的方案具有许多显着的优点，例如使用无毒，中性且廉价的催化剂，环境友好的条件，易于通过过滤分离产物，较短的反应时间，简单的方法和良好的收率。
• Synthesis of magnetic nanoparticles Fe3O4@CQD@Si(OEt)(CH2)3@melamine@TC@Ni(NO3) with application in the synthesis of 2-amino-3-cyanopyridine and pyrano[2,3-c]pyrazole derivatives
  作者：Mehri Solgi、Ardeshir Khazaei、Tahereh Akbarpour

  DOI：10.1007/s11164-022-04702-z

  日期：2022.6

  very effective for the preparation of 2-amino-3-cyanopyridine and pyranopyrazole derivatives in solvent-free conditions. This nanocatalyst was easily separated from the reaction medium using an external magnet and used at least five times in a row under optimal reaction conditions with a slight reduction in the activity of the recycled catalyst. Producing products with good to excellent yields, the need

  在本研究中，碳量子点（CQDs）和有机官能团（Fe 3 O 4 @CQD@Si(OEt)(CH 2 ) 3 @melamine@TC@Ni(NO 3)) 准备好了。为了评估催化剂在有机合成中的效率，研究了2-氨基-3-氰基吡啶和吡喃并吡唑衍生物的制备。通过各种分析方法研究了催化剂的结构和磁性，包括FT-IR、FESEM、TEM、XRD、EDX、EDX映射、TGA和VSM。结果表明，合成的催化剂在无溶剂条件下对制备2-氨基-3-氰基吡啶和吡唑并吡唑衍生物非常有效。这种纳米催化剂很容易使用外部磁体从反应介质中分离出来，并在最佳反应条件下连续使用至少五次，循环催化剂的活性略有降低。生产具有良好收率的产品，需要少量催化剂，这种绿色方法的优点是反应时间短，催化剂可循环使用，在合成2-氨基-3-氰基吡啶和吡喃并吡唑衍生物时不使用有毒溶剂。为了优化反应条件，即温度和催化剂用量的影响，采用了系统的方法，即实验设计（DoE）。
• Sulfonic Acid Supported Phosphonium Based Ionic Liquid Functionalized SBA-15 for the Synthesis of 2-Amino-3-cyano-4,6-diarylpyridines
  作者：Leila Ma'mani、Elham Hajihosseini、Mina Saeedi、Mohammad Mahdavi、Ali Asadipour、Loghman Firoozpour、Abbas Shafiee、Alireza Foroumadi

  DOI：10.1080/15533174.2014.988234

  日期：2016.2.1