diethyl 4-(4-bromophenyl)-1,4-dihydro-1-(4-methoxyphenyl)pyridine-3,5-dicarboxylate | 343806-43-9

• 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-(4-bromophenyl)-1,4-dihydro-1-(4-methoxyphenyl)pyridine-3,5-dicarboxylate
• 英文别名: diethyl 4-(4-bromophenyl)-1-(4-methoxyphenyl)-4H-pyridine-3,5-dicarboxylate
• CAS: 343806-43-9
• 化学式: C₂₄H₂₄BrNO₅
• 分子量: 486.362
• InChiKey: NRUKDXJTJNQPAD-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

• 作为产物：
  描述：

  3,3-二乙氧基丙酸乙酯 、 甲氧苯胺 、 对溴苯甲醛 在 ytterbium(III) triflate 作用下， 以 1,4-二氧六环 为溶剂， 以57%的产率得到diethyl 4-(4-bromophenyl)-1,4-dihydro-1-(4-methoxyphenyl)pyridine-3,5-dicarboxylate
  参考文献：
  名称：

  Ytterbium-catalyzed synthesis of dihydropyridines

  摘要：

  The reaction of anilines, benzaldehydes. and ethyl 3,3-diethoxypropionate in the presence of Yb(OTf)(3) proceeded under mild reaction conditions to give dihydropyridines (DHPs). We have found that the reaction depended on the solvent and the DHPs were obtained selectively in 1,4-dioxane as a solvent. Various 2,6-unsubstituted DHPs were synthesized in one pot in satisfactory yields. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.06.070

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.
• SAUSIN A. EH.; CHEKAVICHUS B. S.; LUSIS V. K.; DUBUR G. YA., XIMIYA GETEROTSIKL. SOEDIN., 1980, HO 4, 493-501
  作者：SAUSIN A. EH.、 CHEKAVICHUS B. S.、 LUSIS V. K.、 DUBUR G. YA.

  DOI：——

  日期：——
• Ytterbium-catalyzed synthesis of dihydropyridines
  作者：Shunsuke Sueki、Ryo Takei、Junya Abe、Isao Shimizu

  DOI：10.1016/j.tetlet.2011.06.070

  日期：2011.8

  The reaction of anilines, benzaldehydes. and ethyl 3,3-diethoxypropionate in the presence of Yb(OTf)(3) proceeded under mild reaction conditions to give dihydropyridines (DHPs). We have found that the reaction depended on the solvent and the DHPs were obtained selectively in 1,4-dioxane as a solvent. Various 2,6-unsubstituted DHPs were synthesized in one pot in satisfactory yields. (C) 2011 Elsevier Ltd. All rights reserved.