2-amino-6-(4-chloro-phenylsulfanyl)-4-phenyl-pyridine-3,5-dicarbonitrile | 285558-50-1

• 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-6-(4-chloro-phenylsulfanyl)-4-phenyl-pyridine-3,5-dicarbonitrile
• 英文别名: 2-amino-6-(4-chlorophenylsulfanyl)-4-(phenyl)pyridine-3,5-dicarbonitrile；2-amino-6-(4-chlorophenylsulfanyl)-4-phenylpyridine-3,5-dicarbonitrile；2-amino-3,5-dicarbonitrile-4-phenyl-6-(4-chlorophenylthio)pyridine；2-amino-6-(4-chlorophenylthio)-4-phenylpyridine-3,5-dicarbonitrile；3,5-Pyridinedicarbonitrile, 2-amino-6-[(4-chlorophenyl)thio]-4-phenyl-；2-amino-6-(4-chlorophenyl)sulfanyl-4-phenylpyridine-3,5-dicarbonitrile
• CAS: 285558-50-1
• 化学式: C₁₉H₁₁ClN₄S
• 分子量: 362.842
• InChiKey: KUXOBBNEYDQQAR-UHFFFAOYSA-N

物化性质

• 熔点：
  228-230 °C(Solv: acetonitrile (75-05-8))
• 沸点：
  623.9±55.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 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：
  5

反应信息

• 作为产物：
  描述：

  在 potassium permanganate 作用下， 以 乙醇 、 水 为溶剂， 反应 0.5h， 生成 2-amino-6-(4-chloro-phenylsulfanyl)-4-phenyl-pyridine-3,5-dicarbonitrile
  参考文献：
  名称：

  K₂CO₃-Mediated, One-Pot, Multicomponent Synthesis of Medicinally Potent Pyridine and Chromeno[2,3-b]pyridine Scaffolds

  摘要：

  An efficient one-pot, multicomponent synthesis of 3,5-dicyanopyridines has been developed from the reaction of malononitrile and different thiophenol or thiols with a variety of aldehydes (aromatic including hindered ones, heteroaromatic, and aliphatic) in the presence of 20 mol% of K2CO3 in refluxing 50% aqeuous ethanol. KMnO4 has been utilized as a readily available, inexpensive oxidant for the in situ transformation of the initially formed dihydropyridine intermediate. K2CO3 also mediates the one-pot formation of chromeno[2,3-b]pyridines from reaction of salicylaldehyde or its analogs with malononitrile and thiol or thiophenols. Both of these conditions also work equally well under 50-fold scale-up conditions.Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2011.555284

文献信息

• 一种三组分一锅法反应制备6-巯基多取代吡 啶衍生物的系统及方法
  申请人：马鞍山市泰博化工科技有限公司

  公开号：CN107417607B

  公开（公告）日：2019-09-17

  本发明公开了一种三组分一锅法反应制备6‑巯基多取代吡啶衍生物的系统及方法，属于有机合成技术领域。本发明的6‑巯基多取代吡啶衍生物的制备系统，包括依次设置的原料混合装置、微波反应装置、抽滤装置、洗涤装置和真空干燥装置，其中，微波反应装置用于对原料混合装置内的反应原料进行微波加热反应，抽滤装置用于对反应所得产物进行抽滤处理，洗涤装置和真空干燥装置用于对抽滤所得滤渣分别进行洗涤和真空干燥处理；本发明是以芳香醛、丙二腈和巯基化合物为反应原料，在碱性离子液体催化剂的催化作用下来制备6‑巯基多取代吡啶衍生物的。本发明中催化剂的催化活性较高，其使用量及循环损失量均较少，所得产物的产率及纯度均较高。
• 2-Hydroxyethylammonium acetate: A reusable task-specific ionic liquid promoting one-pot, three-component synthesis of 2-amino-3,5-dicarbonitrile-6-thio-pyridines
  作者：Sara Sobhani、Moones Honarmand

  DOI：10.1016/j.crci.2012.10.011

  日期：2013.3

  Abstract 2-Hydroxyethylammonium acetate (2-HEAA) as a task-specific ionic liquid, efficiently promotes one-pot three-component reaction of aryl/heteroaryl/alkyl aldehydes with aryl/alkyl thiols and malononitrile at room temperature. This protocol offers several advantages such as using a reusable and cost-effective ionic liquid, being amenable to scale-up and produces the corresponding 2-amino-3,5

  摘要 2-羟基乙基乙酸铵（2-HEAA）作为一种任务特异性离子液体，在室温下可有效促进芳基/杂芳基/烷基醛与芳基/烷基硫醇和丙二腈的一锅三组分反应。该协议提供了几个优点，例如使用可重复使用且具有成本效益的离子液体，易于放大并在短时间内（5 分钟）生产相应的 2-amino-3,5-dicarbonitrile-6-thio-pyridines ) 并且收益良好。
• One-pot, three-component synthesis of highly substituted pyridines and 1,4-dihydropyridines by using nanocrystalline magnesium oxide
  作者：M. Lakshmi Kantam、Koosam Mahendar、Suresh Bhargava

  DOI：10.1007/s12039-010-0007-x

  日期：2010.1

  pot, three component synthesis of 2-amino-4-aryl-3,5-dicyano-6-sulfanylpyridines and the corresponding 1,4-dihydropyridines are from readily accessible starting materials is described. Simply heating of an ethanolic solution of structurally diverse aldehydes with various thiols and malononitrile in the presence of nanocrystalline magnesium oxide provides the highly substituted pyridine derivatives

  描述了2-氨基-4-芳基-3，5-二氰基-6-磺酰基吡啶的一锅三组分合成法，其是从容易获得的起始原料中合成的。在纳米晶状氧化镁的存在下，简单地将结构多样的醛的乙醇溶液与各种硫醇和丙二腈一起加热，即可以中等至高产率获得高度取代的吡啶衍生物，每种衍生物均具有其结构图案，是一种优先的药用支架。反应完成后，可以有效地回收催化剂并以持续的活性进行再利用。
• An Improved Procedure for the Three-Component Synthesis of Highly Substituted Pyridines Using Ionic Liquid
  作者：Brindaban C. Ranu、Ranjan Jana、S. Sowmiah

  DOI：10.1021/jo070015g

  日期：2007.4.1

  A basic ionic liquid, [bmIm]OH, efficiently promotes a one-pot, three-component condensation of aldehydes, malononitrile, and thiophenols to produce highly substituted pyridines in high yields at room temperature. This reaction does not involve any hazardous organic solvent and toxic catalyst. The ionic liquid is recovered and recycled for subsequent reactions.

  碱性离子液体[bmIm] OH可有效促进醛，丙二腈和苯硫酚的一锅三组分缩合反应，从而在室温下以高收率产生高度取代的吡啶。该反应不涉及任何有害的有机溶剂和有毒的催化剂。离子液体被回收并再循环用于随后的反应。
• An efficient procedure for the synthesis of substituted pyridines using KF·Al₂O₃
  作者：Biswanath Das、Bommena Ravikanth、Avula Satya Kumar、Boddu Shashi Kanth

  DOI：10.1002/jhet.206

  日期：2009.11

  Three‐component coupling of aldehydes, malononitrile, and thiophenols has efficiently been carried out at room temperature using potassium fluoride on alumina (KF·Al2O3) as a catalyst to furnish highly substituted pyridines in high yields. J. Heterocyclic Chem., (2009).

  醛，丙二腈和硫酚的三组分偶联已在室温下有效地进行，使用氧化铝上的氟化钾（KF·Al 2 O 3）作为催化剂，可高产率提供高度取代的吡啶。J.杂环化​​学，（2009）。