2-amino-3,5-dicyano-4-(4-methylphenyl)-6-ethoxypyridine | 30504-36-0

• 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-3,5-dicyano-4-(4-methylphenyl)-6-ethoxypyridine
• 英文别名: 2-amino-3,5-dicyano-6-ethoxy-4-(4-methylphenyl)pyridine；2-amino-6-ethoxy-4-p-tolyl-pyridine-3,5-dicarbonitrile；2-Amino-6-ethoxy-4-(4-methylphenyl)pyridine-3,5-dicarbonitrile
• CAS: 30504-36-0
• 化学式: C₁₆H₁₄N₄O
• 分子量: 278.313
• InChiKey: ZBVRVYJCFDUMID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  95.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-amino-3,5-dicyano-4-(4-methylphenyl)-6-ethoxypyridine 在 盐酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 116.0h， 生成 4-Chloro-2-dimethylamino-7-ethoxy-5-p-tolyl-pyrido[2,3-d]pyrimidine-6-carbonitrile
  参考文献：
  名称：

  Synthesis and antihistaminic activity of 2-guanadino-3-cyanopyridines and pyrido[2,3-d]-pyrimidines

  摘要：

  2-Guanadino-3-cyanopyridines 8-33 and pyrido[2,3-d]-pyrimidines 35-52 were synthesized by nucleophilic displacement and cyclization of the chloroamidines 6a-d easily obtained by reaction of 2-aminocyanopyridines 5a-d with phosgene iminium chloride and their action on the release of histamine by mast cells examined under immunological and chemical stimulus, with and without pre-incubation. Several 2-guanadino-3-cyanopyridines and pyrido[2,3-d]-pyrimidines are shown to be inhibitors of the release of histamine when stimulated with ovoalbumin as antigen or with polymer 48/80 as chemical stimulus. Guanadino-3-cyanopyridine 30 and pyrido[2,3-d]-pyrimidine 49 are the more active of all, inhibiting the release of histamine in all the conditions tested (30-60% inhibition). Guanadinocyanopyridines 15, 17, and 19 are very potent stimulators of the release of histamine (150-300%) while pyrido[2,3-d]-pyrimidines are mostly inactive. Compounds 28 and 14 present moderate in vitro cytotoxic activity against P-388, A-549, HT-29, and MEL-28 cell lines. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00108-9
• 作为产物：
  描述：

  乙醇 、 对甲基苯甲醛 、 丙二腈 在 sodium hydroxide 作用下， 反应 4.0h， 以60%的产率得到2-amino-3,5-dicyano-4-(4-methylphenyl)-6-ethoxypyridine
  参考文献：
  名称：

  An efficient synthesis of 2-amino-4-aryl-3,5-dicarbonitrile-6-ethoxypyridine derivatives by the solvent taking part in the reaction

  摘要：

  通过芳香醛、丙二腈和乙醇在NaOH存在下的反应，已经开发出一种高效且简便的2-氨基-4-芳基-3,5-二氰基-6-乙氧基吡啶合成方法，无需使用传统的胺和1,3-二羰基化合物试剂。有趣的是，弱亲核试剂乙醇无需使用强碱催化剂乙醇钠即可参与反应。与现有方法相比，该方法具有产量高、原料易得且反应条件温和等优点。

  DOI：

  10.1007/s11164-012-0829-x

文献信息

• Karimi, Ali R.; Khodadadi, Azam, Letters in Organic Chemistry, 2012, vol. 9, # 6, p. 422 - 426
  作者：Karimi, Ali R.、Khodadadi, Azam

  DOI：——

  日期：——
• Synthesis and antihistaminic activity of 2-guanadino-3-cyanopyridines and pyrido[2,3-d]-pyrimidines
  作者：JoséM. Quintela、Carlos Peinador、Luis Botana、Manuel Estévez、Ricardo Riguera

  DOI：10.1016/s0968-0896(97)00108-9

  日期：1997.8

  2-Guanadino-3-cyanopyridines 8-33 and pyrido[2,3-d]-pyrimidines 35-52 were synthesized by nucleophilic displacement and cyclization of the chloroamidines 6a-d easily obtained by reaction of 2-aminocyanopyridines 5a-d with phosgene iminium chloride and their action on the release of histamine by mast cells examined under immunological and chemical stimulus, with and without pre-incubation. Several 2-guanadino-3-cyanopyridines and pyrido[2,3-d]-pyrimidines are shown to be inhibitors of the release of histamine when stimulated with ovoalbumin as antigen or with polymer 48/80 as chemical stimulus. Guanadino-3-cyanopyridine 30 and pyrido[2,3-d]-pyrimidine 49 are the more active of all, inhibiting the release of histamine in all the conditions tested (30-60% inhibition). Guanadinocyanopyridines 15, 17, and 19 are very potent stimulators of the release of histamine (150-300%) while pyrido[2,3-d]-pyrimidines are mostly inactive. Compounds 28 and 14 present moderate in vitro cytotoxic activity against P-388, A-549, HT-29, and MEL-28 cell lines. (C) 1997 Elsevier Science Ltd.
• An efficient synthesis of 2-amino-4-aryl-3,5-dicarbonitrile-6-ethoxypyridine derivatives by the solvent taking part in the reaction
  作者：Suhui Wang、Sheng Xia、Shimin Tao、Yunyun Zha、Youjian Feng、Liangce Rong

  DOI：10.1007/s11164-012-0829-x

  日期：2013.9

  An efficient and facile synthesis of 2-amino-4-aryl-3,5-dicarbonitrile-6-ethoxypyridine via reaction of aromatic aldehydes, malononitrile, and ethanol in the presence of NaOH has been developed, without using the classic reagents amines and 1,3-dicarbonyl compounds. It is interesting that weak nucleophilic reagent ethanol could take part in the reaction without using strong base catalyst sodium ethylate. Compared with existing methods, the reported process has the advantages of excellent yields, easily obtainable raw materials, and mild reaction conditions.

  通过芳香醛、丙二腈和乙醇在NaOH存在下的反应，已经开发出一种高效且简便的2-氨基-4-芳基-3,5-二氰基-6-乙氧基吡啶合成方法，无需使用传统的胺和1,3-二羰基化合物试剂。有趣的是，弱亲核试剂乙醇无需使用强碱催化剂乙醇钠即可参与反应。与现有方法相比，该方法具有产量高、原料易得且反应条件温和等优点。