dimethyl 4-(pyridin-3-yl)-1,4-dihydropyridine-3,5-dicarboxylate | 1574312-37-0

• 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: dimethyl 4-(pyridin-3-yl)-1,4-dihydropyridine-3,5-dicarboxylate
• 英文别名: dimethyl 1',4'-Dihydro-3,4'-bipyridine-3',5'-dicarboxylate；dimethyl 4-pyridin-3-yl-1,4-dihydropyridine-3,5-dicarboxylate
• CAS: 1574312-37-0
• 化学式: C₁₄H₁₄N₂O₄
• 分子量: 274.276
• InChiKey: JCAZTKVQIYCBTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  77.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-吡啶甲醛 、 丙炔酸甲酯 在 1‑(1‑carboxymethyl)‑3‑methylimidazolium tetrafluoroborate 、 碳酸氢铵 作用下， 以 neat (no solvent) 为溶剂， 反应 0.08h， 以78%的产率得到dimethyl 4-(pyridin-3-yl)-1,4-dihydropyridine-3,5-dicarboxylate
  参考文献：
  名称：

  Ultrasound-mediated synthesis of 4-substituted 1,4-dihydropyridine-3,5-dicarboxylates catalyzed by 1-carboxymethyl-3-methylimidazolium tetrafluoroborate under solvent free condition

  摘要：

  4-Substituted 1,4-dihydropyridine-3,5-dicarboxylates (4) have been synthesized by the solvent-free reaction of aldehyde, methyl propiolate and ammonium carbonate catalyzed by ionic liquid 1-carboxymethyl-3-methylimidazolium tetrafluoroborate under ultrasonic irradiation. The effects of changes in the ultrasonic power, temperature, catalysts and reactants on the synthesis of 4-substituted 1,4-dihydropyridine-3,5-dicarboxylates (4) are discussed. With the optimized reaction conditions, various aldehydes were used to synthesize 1,4-dihydropyridines (4) under the influence of ultrasound irradiation. Compared with the conventional thermal methods, the remarkable advantages of this method are the simple experimental procedure, shorter reaction time (2-10 min) and high yield of product (76-95%). Furthermore, the green catalytic system can be recycled specific times without significantly decreasing the yields and reaction rates. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ultsonch.2014.05.026

文献信息

• Preparation of 6-Unsubstituted 3,4-Dihydropyrimidin-2(1H)-Ones and 2-(Arylamino)Pyrimidines
  作者：S. Terentjeva、D. Muceniece、V. Lusis

  DOI：10.1007/s10593-014-1428-0

  日期：2014.3

  methyl propiolate and of methyl 3-diethylaminoacrylate has yielded a novel series of 6-unsubstituted 3,4-dihydropyrimidin-2(1H)-ones. The successie oxidation of the pyrimidine ring, chlorination of the 2-oxo group, and substitution of the chlorine atom by an aromatic amine give previously unknown 2-(arylamino)pyrimidines. 2-Oxo- and 2-(arylamino)pyrimidine-5-carboxylic acids have been obtained.

  丙酸甲酯和3-二乙基氨基丙烯酸甲酯的Biginelli反应产生了一系列新的6-未取代的3,4-二氢嘧啶-2（1 H）-ones。嘧啶环的成功氧化，2-氧羰基的氯化以及芳族胺对氯原子的取代产生了以前未知的2-（芳基氨基）嘧啶。已经获得了2-氧代和2-（芳基氨基）嘧啶-5-羧酸。