2-amino-4-(4-fluorophenyl)-6-(phenylsulfanyl)pyridine-3,5-dicarbonitrile | 791619-75-5

• 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-(4-fluorophenyl)-6-(phenylsulfanyl)pyridine-3,5-dicarbonitrile
• 英文别名: 2-amino-4-(4-fluorophenyl)-6-phenylsulfanyl-pyridine-3,5-dicarbonitrile；2-amino-4-(4-fluorophenyl)-6-phenylsulfanylpyridine-3,5-dicarbonitrile；2-amino-3,5-dicarbonitrile-4-(4-fluorophenyl)-6-(phenylthio)pyridine；2-amino-4-(4-fluorophenyl)-6-(phenylthio)pyridine-3,5 dicarbonitrile；2-amino-4-(4-fluorophenyl)-6-(phenylthio)pyridine-3,5-dicarbonitrile；2-amino-4-(4-fluorophenyl)6-(phenylthio)pyridine-3,5-dicarbonitrile；2-Amino-4-[4-fluorophenyl]-6-(phenylsulfanyl)pyridine-3,5-dicarbonitrile
• CAS: 791619-75-5
• 化学式: C₁₉H₁₁FN₄S
• 分子量: 346.388
• InChiKey: OOBHXCDUICNMCM-UHFFFAOYSA-N

物化性质

• 熔点：
  248-250 °C
• 沸点：
  588.3±50.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-amino-4-(4-fluorophenyl)-6-(phenylsulfanyl)pyridine-3,5-dicarbonitrile 在 盐酸 、 potassium tert-butylate 、 三乙胺 、 sodium nitrite 作用下， 以 乙二醇二甲醚 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 4-({[3,5-dicyano-4-(4-fluorophenyl)-6-(3-hydroxyazetidin-1-yl)pyridin-2-yl]oxy}methyl)-N-methylpyridine-2-carboxamide
  参考文献：
  名称：

  SUBSTITUTED DICYANOPYRIDINES AND USE THEREOF

  摘要：

  本申请涉及新型取代二氰基吡啶，其制备方法，它们用于治疗和/或预防疾病的用途，以及用于制备治疗和/或预防疾病的药物的用途，特别是用于治疗和/或预防心血管疾病的用途。

  公开号：

  US20130210795A1
• 作为产物：
  描述：

  对氟苯甲醛 在 哌啶 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 2-amino-4-(4-fluorophenyl)-6-(phenylsulfanyl)pyridine-3,5-dicarbonitrile
  参考文献：
  名称：

  A Series of Ligands Displaying a Remarkable Agonistic−Antagonistic Profile at the Adenosine A₁ Receptor

  摘要：

  Adenosine receptor agonists are usually variations of the natural ligand, adenosine. The ribose moiety in the ligand has previously been shown to be of great importance for the agonistic effects of the compound. In this paper, we present a series of nonadenosine ligands selective for the adenosine A(1) receptor with an extraordinary pharmacological profile. 2-Amino-4-benzo[1,3]dioxol-5-yl-6-(2-hydroxyethylsulfanyl)pyridine-3,5-dicarbonitrile (70, LUF 5853) shows full agonistic behavior comparable with the reference compound CPA, while also displaying comparable receptor binding affinity (K-i = 11 nM). In contrast, compound 58 (2-amino-4-(3-trifluoromethylphenyl)-6-(2-hydroxyethylsulfanyl)pyridine-3,5-dicarbonitrile, LUF 5948) has a binding affinity of 14 nM and acts as an inverse agonist. Also present within this same series are compounds that show neutral antagonism of the adenosine A(1) receptor, for example compound 65 (2-amino-4-(4-difluoromethoxyphenyl)-6-(2-hydroxyethylsulfanyl)pyridine-3,5-dicarbonitrile, LUF 5826).

  DOI：

  10.1021/jm049597+

文献信息

• Heterogeneous Cu(<scp>ii</scp>)/<scp>l</scp>-His@Fe₃O₄ nanocatalyst: a novel, efficient and magnetically-recoverable catalyst for organic transformations in green solvents
  作者：Masoomeh Norouzi、Arash Ghorbani-Choghamarani、Mohsen Nikoorazm

  DOI：10.1039/c6ra19776k

  日期：——

  A novel, efficient and green Cu(II)/L-His@Fe3O4 catalyst has been applied successfully in the synthesis of heterocyclic compounds. The resulting catalyst was used in the synthesis of 2,3-dihydroquinazolin-4(1H)-ones, polyhydroquinolines and 2-amino-6-(arylthio)pyridine-3,5-dicarbonitriles as biologically interesting compounds. The present research is focused on investigation of recycling, reusability

  一种新颖，高效，绿色的Cu（II）/ L- His @ Fe 3 O 4催化剂已成功用于杂环化合物的合成。所得催化剂用于合成2，3-二氢喹唑啉-4（1H）-酮，聚氢喹啉和2-氨基-6-（芳硫基）吡啶-3，5-二碳腈作为生物学上感兴趣的化合物。本研究的重点是研究相反应中催化剂的循环利用，可重复使用性和稳定性。Cu（II）/ L -His @ Fe 3 O 4该催化剂至少使用了六次，其活性与新鲜催化剂相当。通过TGA / DTG，EDS，XRD，VSM，FT-IR和SEM对催化剂的化学组成和结构进行了分析。
• DBU-catalyzed three-component one-pot synthesis of highly functionalized pyridines in aqueous ethanol
  作者：Ritu Mamgain、Ram Singh、Diwan S. Rawat

  DOI：10.1002/jhet.32

  日期：2009.1

  1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) efficiently catalyzes three-component one-pot condensations of aldehyde, malononitrile, and thiophenol to produce highly functionalized pyridines in excellent yield in aqueous ethanol. J. Heterocyclic Chem., 46, 69 (2009).

  1,8-二氮杂双环[5.4.0]十一碳-7-烯（DBU）有效催化醛的三组分一锅缩合，丙二腈和苯硫酚在乙醇水溶液中以优异的收率生产高度官能化的吡啶。杂环化学杂志，46，69（2009）。
• Synthesis of 2-amino-4-phenyl-6-(phenylsulfanyl)-3,5-dicyanopyridines by tandem reaction
  作者：Dong Hao、Zhong Yun-lei、Shen Xiao-peng、Yang Jin-ming、Fang Dong

  DOI：10.1007/s11164-012-0984-0

  日期：2014.2

  A novel basic ionic liquid, 1-(2-aminoethyl)pyridinium hydroxide, containing both Brønsted base and Lewis base sites has been used as an efficient catalyst for the synthesis of 2-amino-4-phenyl-6-(phenylsulfanyl)-3,5-dicyanopyridines. The condensation and oxidation tandem reaction of aldehydes, malononitrile, and thiols, performed in aqueous ethanol, afforded reasonable to good yields within 30–60 min. After the reaction, the catalyst could be recycled and reused. A possible mechanism to account for the tandem reaction is proposed. .

  一种新型的基本离子液体，即含有Brønsted碱和Lewis碱位点的1-(2-氨基乙基)吡啶鎓氢氧化物，已被用作合成2-氨基-4-苯基-6-(苯硫基)-3,5-二氰基吡啶的高效催化剂。在水-乙醇体系中进行的醛、丙二腈和硫醇的缩合与氧化串联反应，在30-60分钟内获得了合理至良好的产率。反应结束后，催化剂可以回收并重复使用。提出了一个可能的机制来解释串联反应。
• Application of novel and reusable Fe₃O₄@Co^II(macrocyclic Schiff base ligand) for multicomponent reactions of highly substituted thiopyridine and 4<i>H</i>‐chromene derivatives
  作者：Hakimeh Ebrahimiasl、Davood Azarifar、Jamshid Rakhtshah、Hassan Keypour、Masoumeh Mahmoudabadi

  DOI：10.1002/aoc.5769

  日期：2020.9

  elemental analysis (CHNS). Then, the catalytic performance was successfully investigated in the multicomponent synthesis of 2‐amino‐4‐aryl‐6‐(phenylsulfanyl)pyridine‐3,5‐dicarbonitrile and 2‐amino‐5,10‐dioxo‐4‐aryl‐5,10‐dihydro‐4H‐benzo[g]chromene‐3‐carbonitrile derivatives. Furthermore, the catalyst was isolated using a simple filtration, and recovery of the nanocatalyst was demonstrated five times without

  在本研究中，我们设计并合成了固定在Fe 3 O 4上的Co II（含有1,4-二氮杂pan的大环席夫碱配体）纳米颗粒作为新型，可回收和非均相的催化剂。使用傅立叶变换红外光谱，扫描电子显微镜，透射电子显微镜，X射线衍射，能量色散X射线光谱，热重分析，振动样品磁力分析，差分反射光谱，Brunauere-Emmette等多种技术对纳米材料进行了全面表征–Teller方法，电感耦合等离子体和元素分析（CHNS）。然后，在2-氨基-4-芳基-6（苯硫基）吡啶-3,5-二腈和2-氨基-5,10-二氧代-4-芳基-5的多组分合成中成功地研究了催化性能。 10-二氢-4 H-苯并[ g] chromene-3-腈衍生物。此外，使用简单的过滤分离了催化剂，并且证实了纳米催化剂的回收五次而没有任何活性损失。
• Facile and Rapid Access to Poly Functionalized Pyridine Derivatives
  作者：Pravin V. Shinde、Bapurao B. Shingate、Murlidhar S. Shingare

  DOI：10.1002/cjoc.201190178

  日期：2011.5

  An efficient and greener protocol for the synthesis of poly functionalized pyridines using tetra‐n‐butyl ammonium fluoride (TBAF) in water is established. Remarkable advantages of the present synthetic strategy over the others are shorter reaction times, higher isolated yields, reuse of catalytic system, simple work‐up procedure and more especially its applicability to heteryl and aliphatic aldehydes

  建立了在水中使用四正丁基氟化铵（TBAF）合成多官能吡啶的高效，绿色方案。与其他方法相比，本合成策略的显着优势是反应时间更短，分离产率更高，催化体系可重复使用，后处理步骤简单，尤其是适用于杂醛和脂族醛。