4-(4-dimethylamino-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester | 289476-97-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-(4-dimethylamino-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester
• 英文别名: (4-(4-(dimethylamino)phenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-diyl)diethanone；1-[5-Acetyl-4-[4-(dimethylamino)phenyl]-2,6-dimethyl-1,4-dihydropyridin-3-yl]ethanone；1-[5-acetyl-4-[4-(dimethylamino)phenyl]-2,6-dimethyl-1,4-dihydropyridin-3-yl]ethanone
• CAS: 289476-97-7
• 化学式: C₁₉H₂₄N₂O₂
• 分子量: 312.412
• InChiKey: JTCYEKBSSPXRKV-UHFFFAOYSA-N

物化性质

• 沸点：
  492.9±45.0 °C(Predicted)
• 密度：
  1.093±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  乙酰乙酸乙酯 、 对二甲氨基苯甲醛 在 甲酸铵 作用下， 以 水 为溶剂， 反应 2.5h， 以80%的产率得到4-(4-dimethylamino-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  Light induced synthesis of symmetrical and unsymmetrical dihydropyridines in ethyl lactate–water under tunable conditions

  摘要：

  A highly efficient environment-friendly one-pot green methodology has been developed for the synthesis of symmetrical and unsymmetrical 1,4-dihydropyridines and polyhydroquinolines following the multicomponent Hantzsch synthesis under visible light irradiation in ethyl-L-lactate-water solution at room temperature. The present methodology offers several advantages such as simple procedure, greener condition, excellent yields and short reaction time sans any catalyst, support or promoter. The developed protocol has been materialized with the involvement of a household compact tungsten lamp as the visible light source, and the manifested high selectivity of the reaction performed in ethyl lactate-water solvent mixture under tunable conditions. The Ca2+ channel blocker nitrendipine and nemadipine B were also successfully synthesized applying the developed methodology in high yields. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.10.106

文献信息

• Synthesis and 3D-QSAR study of 1,4-dihydropyridine derivatives as MDR cancer reverters
  作者：Ashish Radadiya、Vijay Khedkar、Abhay Bavishi、Hardevsinh Vala、Shailesh Thakrar、Dhairya Bhavsar、Anamik Shah、Evans Coutinho

  DOI：10.1016/j.ejmech.2014.01.011

  日期：2014.3

  A series of symmetrical and unsymmetrical 1,4-dihydropyridines were synthesized by a rapid, single pot microwave irradiation (MWI) based protocol along with conventional approach and characterized by NMR, IR and mass spectroscopic techniques. The compounds were evaluated for their tumor cell cytotoxicity in HL-60 tumor cells. A 3D-QSAR study using CoMFA and CoMSIA was carried out to decipher the factors governing MDR reversing ability in cancer. The resulting contour maps derived by the best 3D-QSAR models provide a good insight into the molecular features relevant to the biological activity in this series of analogs. 3D contour maps as a result of 3D-QSAR were utilized to identify some novel features that can be incorporated into the 1,4-dihydropyridine framework to enhance the activity. (C) 2014 Elsevier Masson SAS. All rights reserved.