dimethyl 4-(3-methylphenyl)-1,4-dihydropyridine-3,5-dicarboxylate

• 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-(3-methylphenyl)-1,4-dihydropyridine-3,5-dicarboxylate
• 英文别名: 3,5-Dimethyl 4-(3-methylphenyl)-1,4-dihydropyridine-3,5-dicarboxylate
• 化学式: C₁₆H₁₇NO₄
• mdl: MFCD02104449
• 分子量: 287.315
• InChiKey: OGRNKPLEHNFREC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  丙炔酸甲酯 、 3-甲基苯甲醛 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90%的产率得到dimethyl 4-(3-methylphenyl)-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

• Ultrasound-mediated synthesis of 4-substituted 1,4-dihydropyridine-3,5-dicarboxylates catalyzed by 1-carboxymethyl-3-methylimidazolium tetrafluoroborate under solvent free condition
  作者：Jing-Yu He、Hui-Zhen Jia、Qing-Guo Yao、Si-Jie Liu、Hong-Kun Yue、Hong-Wei Yu、Rui-Sheng Hu

  DOI：10.1016/j.ultsonch.2014.05.026

  日期：2015.1

  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.