diethyl 4-(4-chlorophenyl)-1-(4-methoxy-phenyl)-2,6-dimethyl-1,4-dihydropyridine-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-methoxy-phenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
• 英文别名: diethyl 4-(4-chlorophenyl)-1-(4-methoxyphenyl-)2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate；diethyl 1-(4-methoxyphenyl)-2,6-dimethyl-4-(4-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate；Diethyl 4-(4-chlorophenyl)-1-(4-methoxyphenyl)-2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarboxylate；diethyl 4-(4-chlorophenyl)-1-(4-methoxyphenyl)-2,6-dimethyl-4H-pyridine-3,5-dicarboxylate
• 化学式: C₂₆H₂₈ClNO₅
• mdl: MFCD00711212
• 分子量: 469.965
• InChiKey: BDFKTLSPKYBMCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  ethyl (Z)-3-(4-methoxyanilino)-2-butenoate 、 N-pyridinium chloride 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 diethyl 4-(4-chlorophenyl)-1-(4-methoxy-phenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
  参考文献：
  名称：

  用 N-(1-卤代烷基) azinium 卤化物合成杂环的新方法。第五部分 N-取代的 1,4-二氢吡啶的制备

  摘要：

  摘要 在温和和中性条件下，以N-(1-氯烷基)吡啶氯化物形式活化的N-取代烯氨基羰基衍生物和醛，通过亚硫酰氯和吡啶制备了30个N-取代Hantzsch 1,4-二氢吡啶。讨论了该方法的范围。

  DOI：

  10.1080/00397919208021145

文献信息

• Synthesis of 1,4-dihydropyridine esters using low-melting sugar mixtures as green solvents
  作者：J. Ashwin Kumar、Gomathi Shridhar、Savita Ladage、Lakshmy Ravishankar

  DOI：10.1080/00397911.2016.1242750

  日期：2016.12.16

  sugar mixtures (LMMs) were synthesized and used for preparation of 1,4-dihydropyridines with aldehydes, 1,3-dicarbonyl compounds, and a nitrogen source as starting materials. Good yields, low reaction times, recyclability of LMMs, and catalyst-free methodology are some of the highlights of this new protocol. GRAPHICAL ABSTRACT

  摘要 合成了几种低熔点糖混合物 (LMM)，并将其用于以醛、1,3-二羰基化合物和氮源为原料制备 1,4-二氢吡啶。良好的产量、​​低反应时间、LMM 的可回收性和无催化剂方法是该新协议的一些亮点。图形概要
• ZnO Nanoparticle-Catalyzed Multicomponent Reaction for the Synthesis of 1,4-Diaryl Dihydropyridines
  作者：Gagandeep Kour Reen、Monika Ahuja、Ashok Kumar、Rajesh Patidar、Pratibha Sharma

  DOI：10.1080/00304948.2017.1320927

  日期：2017.5.4

  Compounds in the 1,4-dihydropyridine (1,4-DHP) scaffold exhibit a wide range of pharmacological activities. The scaffold is the core of vasodilator, antitubercular, antiviral, antitumorous, antidia...

  1,4-二氢吡啶 (1,4-DHP) 支架中的化合物表现出广泛的药理活性。支架是血管扩张剂、抗结核、抗病毒、抗肿瘤、抗糖尿病...
• Unclassical hydrogen bonds of C–H⋯O and C–H⋯Cl in the crystals of 1,4-diaryl Hantzsch esters
  作者：Xiao-Qing Zhu、Jian-Shuang Wang、Jin-Pei Cheng

  DOI：10.1016/j.tetlet.2004.11.163

  日期：2005.1

  N1-substituted derivatives of Hantzsch ester were synthesized and the molecular structures were studied by using X-ray crystallography. Two types of unclassical hydrogen bonds C–H⋯O and C–H⋯Cl were presented in the crystals. The formation of such a hydrogen bond is dependent on the nature of the substituent at C23.

  合成了三种新型的汉茨酯的N1-取代的衍生物，并利用X射线晶体学研究了其分子结构。晶体中存在两种类型的非经典氢键C–H⋯O和C–H⋯Cl。这种氢键的形成取决于C 23上取代基的性质。
• 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.
• Multicomponent reactions leading to symmetric and asymmetric multi-substituted 1,4-dihydropyridines on montmorillonite
  作者：Yu-peng Liu、Jin-ming Liu、Xin Wang、Tie-ming Cheng、Run-tao Li

  DOI：10.1016/j.tet.2013.04.006

  日期：2013.6

  Highly functionalized multi-substituted symmetric and asymmetric 1,4-dihydropyridines were concisely synthesized in moderate to good yields via one-pot multicomponent reactions (MCRs) of beta-dicarbonyl compounds, aldehydes and amines at room temperature on montmorillonite. The merits of this method include the environmentally friendly reaction conditions, simple operation, broad substrate, satisfied yields and the reuse of the montmorillonite. (C) 2013 Elsevier Ltd. All rights reserved.