diethyl 4-(4-chlorophenyl)-1,4-dihydro-1-(4-methoxyphenyl)pyridine-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: diethyl 4-(4-chlorophenyl)-1,4-dihydro-1-(4-methoxyphenyl)pyridine-3,5-dicarboxylate
• 英文别名: diethyl 4-(4-chlorophenyl)-1-(4-methoxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylate；diethyl 4-(4-chlorophenyl)-1-(4-methoxyphenyl)-4H-pyridine-3,5-dicarboxylate
• 化学式: C₂₄H₂₄ClNO₅
• 分子量: 441.911
• InChiKey: OPDVPIHZSFXKRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 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：

  (E)-N-(4-chlorobenzylidene)-4-methoxyaniline 、 丙炔酸乙酯 在 scandium tris(trifluoromethanesulfonate) 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以54%的产率得到diethyl 4-(4-chlorophenyl)-1,4-dihydro-1-(4-methoxyphenyl)pyridine-3,5-dicarboxylate
  参考文献：
  名称：

  Catalytic synthesis of 1,4-dihydropyridine derivatives using scandium(III) triflate

  摘要：

  Scandium(III) triflate smoothly catalyzed the reaction of imines with ethyl propiolate (2.5 equiv) to produce the corresponding N-substituted 1,4-dihydropyridines in good yields in toluene or BTF under reflux conditions. It also catalyzed the reaction of aniline and ethyl propiolate (3.2 equiv) to give another 1,4-dihydropyridine bearing three ester groups in moderate yield under the same conditions. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.11.003

文献信息

• Multicomponent Reactions for Diverse Synthesis of<i>N</i>-Substituted and NH 1,4-Dihydropyridines
  作者：Jieping Wan、Youyi Zhou、Yunyun Liu、Zheng Fang、Chengping Wen

  DOI：10.1002/cjoc.201300918

  日期：2014.3

  The multicomponent reactions of aldehydes, electron deficient alkynes and amines have been successfully performed to yield a number of symmetrical 2,6‐unsubstituted 1,4‐dihydropyridines (1,4‐DHPs). This method has been found generally applicable for the synthesis of both N‐substituted and N‐unsubstituted 1,4‐DHPs by employing secondary amine to activate the alkyne component via enaminoester intermediates

  醛，缺乏电子的炔烃和胺的多组分反应已成功进行，得到了许多对称的2,6-未取代的1,4-二氢吡啶（1,4-DHPs）。已经发现该方法通常可用于合成N-取代的和N-未取代的1,4-DHP，方法是使用仲胺通过烯胺酯中间体活化炔烃组分。本方法通过烯胺型活化进行，这不同于采用AcOH作为溶剂的已知方法。
• Discovery of novel 1,4-dihydropyridine-based PDE4 inhibitors
  作者：Rajamohan R. Poondra、Ratnam V. Nallamelli、Chandana Lakshmi Teja Meda、B.N.V. Srinivas、Anushka Grover、Jyotsna Muttabathula、Sreedhara R. Voleti、Balasubramanian Sridhar、Manojit Pal、Kishore V.L. Parsa

  DOI：10.1016/j.bmcl.2012.11.121

  日期：2013.2

  Substituted 1,4-dihydropyridines were discovered as a novel and potent series of phosphodiesterase 4 (PDE4) inhibitors. Structure-activity relationships within this series have been carried out and studies revealed that the dihydropyridine core, with indole moiety and 3,4-dimethoxybenzyl group, is a potent analogue for PDE4 inhibition. These novel series of compounds were prepared via a 3-component reaction in a single pot. In vitro biological activity, modeling studies and crystallography data are also reported. (C) 2012 Elsevier Ltd. All rights reserved.
• 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.
• Catalytic synthesis of 1,4-dihydropyridine derivatives using scandium(III) triflate
  作者：Satoshi Kikuchi、Masahiro Iwai、Hiroyuki Murayama、Shin-ichi Fukuzawa

  DOI：10.1016/j.tetlet.2007.11.003

  日期：2008.1

  Scandium(III) triflate smoothly catalyzed the reaction of imines with ethyl propiolate (2.5 equiv) to produce the corresponding N-substituted 1,4-dihydropyridines in good yields in toluene or BTF under reflux conditions. It also catalyzed the reaction of aniline and ethyl propiolate (3.2 equiv) to give another 1,4-dihydropyridine bearing three ester groups in moderate yield under the same conditions. (c) 2007 Elsevier Ltd. All rights reserved.