diethyl 2,6-diphenyl-1,4-dihydropyridine-3,5-dicarboxylate | 70677-66-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: diethyl 2,6-diphenyl-1,4-dihydropyridine-3,5-dicarboxylate
• 英文别名: 2,6-diphenyl-3,5-diethoxycarbonyl-1,4-dihydropyridine；2,6-diphenyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester；2,6-Diphenyl-1,4-dihydro-pyridin-3,5-dicarbonsaeure-diaethylester
• CAS: 70677-66-6
• 化学式: C₂₃H₂₃NO₄
• 分子量: 377.44
• InChiKey: SMVFPLYORDJAIM-UHFFFAOYSA-N

物化性质

• 熔点：
  134-136 °C
• 沸点：
  545.0±50.0 °C(Predicted)
• 密度：
  1.188±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  28
• 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：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl 2,6-diphenyl-1,4-dihydropyridine-3,5-dicarboxylate 在 chromium(VI) oxide 、 三氯化铝 、 氯化亚砜 、 溶剂黄146 、 硝基苯 作用下， 生成 diindeno[1,2-b:2',1'-e]pyridine-10,12-dione
  参考文献：
  名称：

  Borsche; Hahn, Justus Liebigs Annalen der Chemie, 1939, vol. 537, p. 219,242

  摘要：

  DOI：
• 作为产物：
  描述：

  diethyl 2,4-dibenzoylpentanedioate 在 ammonium acetate 作用下， 以 乙醇 为溶剂， 以58%的产率得到diethyl 2,6-diphenyl-1,4-dihydropyridine-3,5-dicarboxylate
  参考文献：
  名称：

  铁催化的N-甲基胺的选择性氧化：亚甲基桥连的双-1,3-二羰基化合物的高效合成

  摘要：

  亚铁桥联的双1,3-二羰基衍生物是通过铁催化的1,3-二羰基化合物与N，N-二甲基苯胺的氧化反应而有效合成的。联吡唑和取代的1,4-二氢吡啶分别通过双-1,3-二羰基化合物与肼和乙酸铵的反应制得。

  DOI：

  10.1021/ol901751c

文献信息

• Aqueous CO₂ fixation: construction of pyridine skeletons in cooperation with ammonium cations
  作者：Shiqun Xiang、Weibin Fan、Wei Zhang、Yinghua Li、Shiwei Guo、Deguang Huang

  DOI：10.1039/d1gc02303a

  日期：——

  synthesis of fused pyridines by [2 + 2 + 1 + 1] the cycloaddition of ketones with an ammonium cation under a CO2 atmosphere. The reactions employed ammonium cation as a nitrogen source and CO2 gas as a carbon source in an aqueous solution. Monoethanolamine (MEA) was used as an additive to increase the solubility of CO2 in an aqueous solution. The scope and versatility of the method are demonstrated with 38

  通过 [2 + 2 + 1 + 1] 酮与铵阳离子在 CO 2气氛下的环加成，探索了一种简单且绿色的合成稠合吡啶的方法。该反应在水溶液中使用铵阳离子作为氮源和CO 2气体作为碳源。单乙醇胺（MEA）用作添加剂以增加CO 2在水溶液中的溶解度。该方法的范围和多功能性通过 38 个示例进行了演示。发现产品具有光敏性，并显示出作为有机光电材料的潜在应用。在实验研究的基础上提出了一种selectfluor促进的反应机理。我们的工作非常出色，因为它是一个不含金属的系统，使用 CO 2 作为碳源和 MEA 作为水性合成中的添加剂。
• Intermolecular Aryne Ene Reaction of Hantzsch Esters: Stable Covalent Ene Adducts from a 1,4-Dihydropyridine Reaction
  作者：Piera Trinchera、Weitao Sun、Jane E. Smith、David Palomas、Rachel Crespo-Otero、Christopher R. Jones

  DOI：10.1021/acs.orglett.7b02272

  日期：2017.9.1

  2-dihydropyridines or 2-methylene-3-aryl-1,2,3,4-tetrahydropyridines via a regioselective C-2 or C-3 arylation. These compounds are the first series of isolable and bench-stable covalent ene adducts formed between dihydropyridines and unsaturated substrates. Experimental studies and DFT calculations provide mechanistic support for a concerted intermolecular aryne ene process, which may have implications for NAD(P)H

  芳烃与1，4-二氢吡啶的反应通过区域选择性的C-2或C-3芳基化反应得到2-芳基-1,2-二氢吡啶或2-亚甲基-3-芳基-1,2,3,4-四氢吡啶。这些化合物是在二氢吡啶和不饱和底物之间形成的第一组可分离且稳定的共价烯加合物。实验研究和DFT计算为协同的分子间亚芳烃工艺提供了机械支持，这可能对NAD（P）H模型反应有影响。
• A metal-free strategy for the cross-dehydrogenative coupling of 1,3-dicarbonyl compounds with 2-methoxyethanol
  作者：Vishal Suresh Kudale、Sheng Zheng、Sheng-Hua Huang、Yu-Lun Chang、Jeh-Jeng Wang

  DOI：10.1039/d1ob02290c

  日期：——

  we report a metal-free approach for the construction of methylene-bridged bis-1,3-dicarbonyl compounds via cross-dehydrogenative coupling of 1,3-dicarbonyl compounds with 2-methoxyethanol. In addition, we have extended this methodology to synthesize tetra-substituted pyridine derivatives using 1,3-dicarbonyl, 2-methoxyethanol and NH4OAc in one step. The key advantages include accepting a wide range

  在这里，我们报告了一种通过1,3-二羰基化合物与 2-甲氧基乙醇的交叉脱氢偶联来构建亚甲基桥连双 1,3-二羰基化合物的无金属方法。此外，我们扩展了这一方法，以一步合成四取代吡啶衍生物，使用 1,3-二羰基、2-甲氧基乙醇和 NH 4 OAc。主要优势包括接受广泛的底物，利用 O 2作为唯一氧化剂，以及合成生物活性化合物，如 1,4-二氢吡啶和吡唑。
• Photoinduced Proton Transfer Promoted by Peripheral Subunits for Some Hantzsch Esters
  作者：Sébastien Azizi、Gilles Ulrich、Maud Guglielmino、Stéphane le Calvé、Jerry P. Hagon、Anthony Harriman、Raymond Ziessel

  DOI：10.1021/jp5078246

  日期：2015.1.8

  It is noted that, for a small series of 3,5-diacetyl-1,4-dihydrolutidine (DDL) derivatives and the corresponding Hantzsch esters, the presence of methyl groups at the 2,6-positions serves to extinguish fluorescence in solution but not in the solid state. Emission is weakly activated and affected by changes in solvent polarity. The latter situation arises because the optical transition involves intramolecular charge transfer. Calculations, both semiempirical and DFT, indicate that, in all cases, rotation of the carbonyl function is facile and that the dihydropyridine ring is planar. These calculations also indicate that the 2,6-methyl groups do not affect the generic structure of the molecule. It is proposed that illumination increases the molecular dipole moment and pushes electron density toward the carbonyl oxygen atom. Proton transfer can now occur from one of the methyl groups, leading to formation of a relatively low-energy, neutral intermediate, followed by a second proton transfer step that forms the enol. Reaction profiles computed for the ground-state species indicate that this route is highly favored relative to hydrogen transfer from the 4-position. The barriers for light-induced proton transfer are greatly reduced relative to the ground-state process but such large-scale structural transformations are hindered in the solid state. A rigid analogue that cannot form an enol is highly emissive in solution, supporting the conclusion that proton transfer is in competition to fluorescence in solution.
• Sugimoto, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1944, vol. 64, # 3, p. 192,195
  作者：Sugimoto

  DOI：——

  日期：——