dimethyl 1,4-dihydro-4-(4-methoxyphenyl)pyridine-3,5-dicarboxylate | 56820-26-9

• 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: dimethyl 1,4-dihydro-4-(4-methoxyphenyl)pyridine-3,5-dicarboxylate
• 英文别名: dimethyl 4-(4-methoxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylate；4-(4-methoxy-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid dimethyl ester
• CAS: 56820-26-9
• 化学式: C₁₆H₁₇NO₅
• 分子量: 303.315
• InChiKey: JAAFCACWWCLZFF-UHFFFAOYSA-N

物化性质

• 熔点：
  197-198.5 °C(Solv: methanol (67-56-1))
• 沸点：
  442.6±45.0 °C(Predicted)
• 密度：
  1.220±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dimethyl 1,4-dihydro-4-(4-methoxyphenyl)pyridine-3,5-dicarboxylate 在 sodium hydride 作用下， 反应 2.0h， 生成 (4aR,4bR,8aR,8bR)-4,8-Bis-(4-methoxy-phenyl)-1,5-dimethyl-1,5,8,8b-tetrahydro-4H,4bH-cyclobuta[1,2-b;3,4-b']dipyridine-3,4a,7,8a-tetracarboxylic acid tetramethyl ester
  参考文献：
  名称：

  二聚体4-芳基-1,4-二氢吡啶的新型固态合成

  摘要：

  在固态辐射下，4-芳基-1,4-二氢吡啶1经历[2 + 2]环二酮至中心对称的头对尾二聚体3和4a。该笼二聚体几乎只形成3 经由与c 2 -对称顺-dimers 2发生在几乎定量的产率，在与所述的环加成反应对比度抗-dimer 4a中，这是伴随着光氧化，以吡啶5a中。

  DOI：

  10.1002/jhet.5570350217
• 作为产物：
  描述：

  4-甲氧基苯甲醛 、 丙炔酸甲酯 在 碳酸氢铵 、 溶剂黄146 作用下， 反应 0.25h， 生成 dimethyl 1,4-dihydro-4-(4-methoxyphenyl)pyridine-3,5-dicarboxylate
  参考文献：
  名称：

  Photodimerization of 4-Aryl-1,4-dihydropyridines in 1-Butyl-3-methylimidazolium Tetrafluoroborate

  摘要：

  开发了一种简单、高效、便利的方法，用于在室温离子液体1-丁基-3-甲基咪唑四氟硼酸盐（[Bmim][BF4]）中进行4-芳基-1,4-二氢吡啶的光二聚化。通过这种方法，得到了头尾连接的同聚二聚体和3,9-二氮四星烷，产率良好至极佳。此外，[Bmim][BF4]作为反应介质可重复使用至少5次，反应时间和产率没有明显下降。

  DOI：

  10.1246/cl.140513

文献信息

• Solid-state Synthesis of Novel 3,9-Diazatetraasteranes
  作者：Andreas Hilgeroth

  DOI：10.1246/cl.1997.1269

  日期：1997.12

  A novel solid-state synthesis of 3,9-diazatetraasteranes is reported, giving polyfunctionalized derivates in a single-step reaction with nearly quantitative yields by photochemically induced [2+2]cycloaddition reactions.

  报道了一种新型的 3,9-二氮杂四甾烷的固态合成，通过光化学诱导的 [2+2] 环加成反应，在一步反应中以几乎定量的产率得到多官能化衍生物。
• Novel Solid-State Synthesis of Polyfunctionalized 3,9-Diazatetraasteranes
  作者：Andreas Hilgeroth、Ute Baumeister、Frank W. Heinemann

  DOI：10.1002/(sici)1099-0690(199806)1998:6<1213::aid-ejoc1213>3.0.co;2-u

  日期：1998.6

  of 3 was confirmed by 1H NMR spectral data as well as by X-ray crystal structure analysis. The dimerization reactions prove to be topochemically controlled by the nearest distance between potentially reacting double bonds, as well as by the conformationally determined packing restraints. This latter factor is shown by the X-ray crystal structure analysis of one dimerizing and one photostable derivative

  辐射后，结晶的4-甲氧基苯基-1,4-二氢吡啶3经历几乎定量的[2 + 2]环加成反应，通过开环中间体2形成中心对称的多官能化3,9-二氮杂四环烷3。1 H NMR光谱数据以及X射线晶体结构分析证实了3的中心对称性。事实证明，二聚化反应是由可能发生反应的双键之间的最近距离以及由构象确定的堆积约束进行拓扑化学控制的。通过单体1的一种二聚化和一种光稳定的衍生物的X射线晶体结构分析显示了后者的因素。
• Solid-state formation of centrosymmetric cage dimeric 4-aryl-1,4-dihydropyridines via non-symmetricsyn-dimers studied by13C cross-polarization magic angle spinning NMR spectroscopy
  作者：Andreas Hilgeroth、Günter Hempel、Ute Baumeister、Detlef Reichert

  DOI：10.1002/(sici)1097-458x(199905)37:5<376::aid-mrc458>3.0.co;2-o

  日期：1999.5

  The solid‐state formation of a centrosymmetric cage dimeric 4‐aryl‐1,4‐dihydropyridine was monitored by 13C cross polarization magic angle spinning (CP/MAS) NMR spectroscopy. The spectra of the photodimerizing derivatives document the changes in symmetry during the reaction and the reaction progress. Furthermore, they clearly reflect characterizing conformational properties of the molecules. Starting

  通过 13C 交叉极化魔角旋转 (CP/MAS) NMR 光谱监测中心对称笼二聚体 4-芳基-1,4-二氢吡啶的固态形成。光二聚衍生物的光谱记录了反应和反应过程中对称性的变化。此外，它们清楚地反映了分子的表征构象特性。从单体分子的中心对称对开始，二聚化进行到非对称同型二聚体，然后环化为中心对称笼二聚体。因此，13C CP/MAS NMR 光谱的应用证明了固态光二聚化中不寻常的对称性破坏。版权所有 © 1999 中国化工学会
• Ultrasound-mediated synthesis of 4-substituted 1,4-dihydropyridine-3,5-dicarboxylates catalyzed by 1-carboxymethyl-3-methylimidazolium tetrafluoroborate under solvent free condition
  作者：Jing-Yu He、Hui-Zhen Jia、Qing-Guo Yao、Si-Jie Liu、Hong-Kun Yue、Hong-Wei Yu、Rui-Sheng Hu

  DOI：10.1016/j.ultsonch.2014.05.026

  日期：2015.1

  4-Substituted 1,4-dihydropyridine-3,5-dicarboxylates (4) have been synthesized by the solvent-free reaction of aldehyde, methyl propiolate and ammonium carbonate catalyzed by ionic liquid 1-carboxymethyl-3-methylimidazolium tetrafluoroborate under ultrasonic irradiation. The effects of changes in the ultrasonic power, temperature, catalysts and reactants on the synthesis of 4-substituted 1,4-dihydropyridine-3,5-dicarboxylates (4) are discussed. With the optimized reaction conditions, various aldehydes were used to synthesize 1,4-dihydropyridines (4) under the influence of ultrasound irradiation. Compared with the conventional thermal methods, the remarkable advantages of this method are the simple experimental procedure, shorter reaction time (2-10 min) and high yield of product (76-95%). Furthermore, the green catalytic system can be recycled specific times without significantly decreasing the yields and reaction rates. (C) 2014 Elsevier B.V. All rights reserved.
• Cage DimericN-Acyl- andN-Acyloxy-4-aryl-1,4-dihydropyridines as First Representatives of a Novel Class of HIV-1 Protease Inhibitors
  作者：Andreas Hilgeroth、Andreas Billich

  DOI：10.1002/(sici)1521-4184(199911)332:11<380::aid-ardp380>3.0.co;2-t

  日期：1999.11

  The synthesis of a series of novel cage dimeric N-acyl and N-acyl-oxy-3-aryl-1,4-dihydropyridines starting either from solid-state synthetic ester dimers or hom monomeric 4-aryl-1,4-dihydropyridines is presented. Their biological evaluation as novel HIV-1 protease inhibitors showed the most active compounds to be 5c and 5i with inhibitory activities of 52% (50 mu M) and 49% (25 mu M), respectively. Within each series of N-acyl- and N-acyloxy derivatives NCOBz and NBoc groups were found to be the best substituents. Although they exhibiting only moderate activities these cage dimers hold promise as a class of novel non-peptidic HIV-1 protease inhibitors.