diethyl 1-(4-bromophenyl)-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylate | 136886-16-3

• 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 1-(4-bromophenyl)-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylate
• 英文别名: diethyl 1-(4-bromophenyl)-4-phenyl-4H-pyridine-3,5-dicarboxylate
• CAS: 136886-16-3
• 化学式: C₂₃H₂₂BrNO₄
• 分子量: 456.336
• InChiKey: XRDIFEJDFBVJCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  苯甲醛 、 4-溴苯胺 、 丙炔酸乙酯 以 溶剂黄146 为溶剂， 反应 0.5h， 以31%的产率得到diethyl 1-(4-bromophenyl)-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylate
  参考文献：
  名称：

  Synthesis and electrochemical oxidation of 1-aryl-3,5-diethoxycarbonyl-2,6-unsubstituted 1,4-dihydropyridines

  摘要：

  DOI：

  10.1007/bf00474235

文献信息

• Studies on chemoselective synthesis of 1,4- and 1,2-dihydropyridine derivatives by a Hantzsch-like reaction: a combined experimental and DFT study
  作者：Peng Li、Shijie Wang、Nana Tian、Hong Yan、Juan Wang、Xiuqing Song

  DOI：10.1039/d0ob02289f

  日期：——

  propiolate as raw materials. The mechanisms for the formation of 1,4-DHP and 1,2-DHP were proposed based on the isolated intermediate named diethyl 4-((phenylamino)methylene)pent-2-enedioate generated by the Michael addition of aniline and ethyl propiolate. The transition state structures were optimized and the reaction energy barriers of intermediates in the speculated mechanisms were calculated by DFT

  在通过类 Hantzsch 反应制备 3,5-二羧酸二乙酯-1,4-二氢吡啶 (1,4-DHP) 的实验过程中，发现副产物 3,5-二羧酸二乙酯-1，反应生成2-二氢吡啶(1,2-DHP)。为探讨这一现象，以芳香胺、芳香醛和丙炔酸乙酯为原料，研究了反应条件对1,4-DHP和1,2-DHP收率的影响。1,4-DHP 和 1,2-DHP 的形成机理基于苯胺和丙炔酸乙酯的迈克尔加成生成的名为 4-((苯基氨基)亚甲基)戊二烯二酸二乙酯的分离中间体提出。在M062X/def2TZVP//B3LYP-D3/def-SVP水平上，通过DFT计算，优化了过渡态结构，并计算了推测机理中中间体的反应能垒。发现中间体的反应能垒和主要构型IM2和IM3'是化学选择性的决定因素。总之，这些结果表明，通过类 Hantzsch 反应合成 1,4-DHP 和 1,2-DHP 具有高化学选择性，并且在不同条件下可以很容易地获得
• 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.