diethyl 4-(3-bromophenyl)-1-(2-methoxyphenyl)-4H-pyridine-3,5-dicarboxylate | 1430853-57-8

• 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: diethyl 4-(3-bromophenyl)-1-(2-methoxyphenyl)-4H-pyridine-3,5-dicarboxylate
• CAS: 1430853-57-8
• 化学式: C₂₄H₂₄BrNO₅
• 分子量: 486.362
• InChiKey: IJFHAFLOLXJGGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl 4-(3-bromophenyl)-1-(2-methoxyphenyl)-4H-pyridine-3,5-dicarboxylate 、 丙烯酸甲酯（MA） 在 bis-triphenylphosphine-palladium(II) chloride 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.25h， 生成 (E)-diethyl 4-(3-(3-methoxy-3-oxoprop-1-en-1-yl)phenyl)-1-(2-methoxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylate
  参考文献：
  名称：

  Montmorillonite K-10 catalyzed green synthesis of 2,6-unsubstituted dihydropyridines as potential inhibitors of PDE4

  摘要：

  Montmorillonite K-10 mediated MCR of anilines, arylaldehydes and ethyl-3,3-diethoxypropionate in water afforded 2,6-unsubstituted dihydropyridines depending on the nature of anilines employed. A variety of dihydropyridines were prepared by using this green methodology in good yields and montmorillonite K-10 was found to be an inexpensive and reusable catalyst. The structure elaboration of a representative compound was carried out under Heck conditions. Some of the compounds synthesized showed significant inhibition of PDE4B when tested in vitro. Docking studies indicated that one of the ester moieties of these compounds played a key role in their interactions with the PDE4B protein. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.12.052
• 作为产物：
  描述：

  间溴苯甲醛 、 3,3-二乙氧基丙酸乙酯 、 邻甲氧基苯胺 在 montmorillonite K-10 作用下， 以 水 为溶剂， 反应 6.0h， 以81%的产率得到diethyl 4-(3-bromophenyl)-1-(2-methoxyphenyl)-4H-pyridine-3,5-dicarboxylate
  参考文献：
  名称：

  Montmorillonite K-10 catalyzed green synthesis of 2,6-unsubstituted dihydropyridines as potential inhibitors of PDE4

  摘要：

  Montmorillonite K-10 mediated MCR of anilines, arylaldehydes and ethyl-3,3-diethoxypropionate in water afforded 2,6-unsubstituted dihydropyridines depending on the nature of anilines employed. A variety of dihydropyridines were prepared by using this green methodology in good yields and montmorillonite K-10 was found to be an inexpensive and reusable catalyst. The structure elaboration of a representative compound was carried out under Heck conditions. Some of the compounds synthesized showed significant inhibition of PDE4B when tested in vitro. Docking studies indicated that one of the ester moieties of these compounds played a key role in their interactions with the PDE4B protein. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.12.052

文献信息

• Montmorillonite K-10 catalyzed green synthesis of 2,6-unsubstituted dihydropyridines as potential inhibitors of PDE4
  作者：T. Ram Reddy、G. Rajeshwar Reddy、L. Srinivasula Reddy、Chandana Lakshmi T. Meda、Kishore V.L. Parsa、K. Shiva Kumar、Y. Lingappa、Manojit Pal

  DOI：10.1016/j.ejmech.2012.12.052

  日期：2013.4

  Montmorillonite K-10 mediated MCR of anilines, arylaldehydes and ethyl-3,3-diethoxypropionate in water afforded 2,6-unsubstituted dihydropyridines depending on the nature of anilines employed. A variety of dihydropyridines were prepared by using this green methodology in good yields and montmorillonite K-10 was found to be an inexpensive and reusable catalyst. The structure elaboration of a representative compound was carried out under Heck conditions. Some of the compounds synthesized showed significant inhibition of PDE4B when tested in vitro. Docking studies indicated that one of the ester moieties of these compounds played a key role in their interactions with the PDE4B protein. (C) 2013 Elsevier Masson SAS. All rights reserved.