diethyl 1,2-diphenyl-1,2-dihydropyridine-3,5-dicarboxylate | 1446307-49-8

• 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 1,2-diphenyl-1,2-dihydropyridine-3,5-dicarboxylate
• 英文别名: diethyl 1,2-diphenyl-2H-pyridine-3,5-dicarboxylate
• CAS: 1446307-49-8
• 化学式: C₂₃H₂₃NO₄
• 分子量: 377.44
• InChiKey: RWSYIESJIZTYLX-UHFFFAOYSA-N

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：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl 1,2-diphenyl-1,2-dihydropyridine-3,5-dicarboxylate 在 Ir[dF(CF₃)ppy]2(dtbbpy)PF₆ 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以80 %的产率得到tetraethyl 1,2,7,8-tetraphenyl-1,7,8,8b-tetrahydrocyclobuta[1,2-b:4,3-c']dipyridin-e-3,4a,5,8a(2H,4bH)-tetracarboxylate
  参考文献：
  名称：

  可见光催化的 1,2-二氢吡啶分子间 [2+2] 环加成：实验和 DFT 相结合的研究

  摘要：

  该文首次通过可见光催化实现了1,2-二氢吡啶的分子间[2+2]环加成反应。在蓝色 LED 灯的照射下，用可见光催化剂高效合成了一系列新型复杂的环丁烷衍生物，即 1,2-二芳基-1,2-二氢吡啶-3,5-二羧酸二乙酯的二聚体。密度泛函理论和时间相关的密度泛函理论被用来阐明详细的反应过程，例如反应机理和环加成产物的立体选择性。

  DOI：

  10.1016/j.tet.2023.133357
• 作为产物：
  描述：

  ethyl 3-(allylamino)acrylate 在 三氟乙酸 作用下， 以 乙腈 、 苯 为溶剂， 反应 4.0h， 生成 diethyl 1,2-diphenyl-1,2-dihydropyridine-3,5-dicarboxylate
  参考文献：
  名称：

  Cascade synthesis of 1,2-dihydropyridine from dienaminodioate and an imine: a three-component approach

  摘要：

  A convenient synthesis of 1,2-dihydropyridine (1,2-DHP) has been developed from dienaminodioate and an imine mediated by trifluoroacetic acid in a one-pot cascade synthesis. The advantages associated with this transformation include conditions that are metal-free, room temperature, undistilled solvent, and expeditious in excellent yields. The substrate scope has been demonstrated with various aromatic, heteroaromatic, unsaturated aldehydes, and anilines, benzylic amines in impressive yields. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.05.037

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
• A comprehensive discussion on photophysical properties of dihydropyridines: Experimental and theoretical studies
  作者：Yimeng He、Huiqin Wang、Changwei Ge、Hong Yan

  DOI：10.1016/j.molstruc.2023.135167

  日期：2023.6

  In this article, the photophysical properties of DHPs, including 1,2-DHPs and 1,4-DHPs, were studied experimentally and theoretically. Their structural differences bring about different photophysical properties, and also lead to different photochemical properties. Specifically, a series of different substituted 1,2-DHPs and 1,4-DHPs were synthesized to measure their UV–Vis absorption and fluorescence

  本文从实验和理论上对DHPs(包括1,2-DHPs和1,4-DHPs)的光物理性质进行了研究。它们的结构差异带来了不同的光物理性质，也导致了不同的光化学性质。具体而言，合成了一系列不同取代的 1,2-DHP 和 1,4-DHP，以测量它们在稀释溶液中的紫外-可见吸收和荧光发射光谱，并在密度泛函理论 (DFT) 水平上进行了理论计算。为了描述 DHP 的反应性，使用时间相关密度泛函理论 (TDDFT) 来优化它们的基态和激发态结构，并在 B3LYP-D3/def2-TZVP 水平上计算它们的电子激发能量。前沿分子轨道和电子空穴分布分析用于说明电子跃迁类型。不同 DHP 的基态和激发态结构之间的差异通过进行均方根偏差 (RMSD) 分析来表征。
• Cascade synthesis of 1,2-dihydropyridine from dienaminodioate and an imine: a three-component approach
  作者：Chandrasekhar Challa、Manju John、Ravi S. Lankalapalli

  DOI：10.1016/j.tetlet.2013.05.037

  日期：2013.7

  A convenient synthesis of 1,2-dihydropyridine (1,2-DHP) has been developed from dienaminodioate and an imine mediated by trifluoroacetic acid in a one-pot cascade synthesis. The advantages associated with this transformation include conditions that are metal-free, room temperature, undistilled solvent, and expeditious in excellent yields. The substrate scope has been demonstrated with various aromatic, heteroaromatic, unsaturated aldehydes, and anilines, benzylic amines in impressive yields. (C) 2013 Elsevier Ltd. All rights reserved.
• Visible light-catalyzed intermolecular [2+2] cycloaddition of 1,2-dihydropyridines: A combined experimental and DFT study
  作者：Yimeng He、Huiqin Wang、Yifan Yang、Hong Yan

  DOI：10.1016/j.tet.2023.133357

  日期：2023.3

  In this article, the intermolecular [2+2] cycloaddition of 1,2-dihydropyridines was achieved for the first time by visible light-catalyzed. A series of novel and complex cyclobutane derivatives, the dimers of diethyl 1,2-diaryl-1,2-dihydropyridine-3,5-dicarboxylate, were synthesized efficiently with visible light catalysts under the irradiation of blue LED lamps. The density functional theory and time-dependent

  该文首次通过可见光催化实现了1,2-二氢吡啶的分子间[2+2]环加成反应。在蓝色 LED 灯的照射下，用可见光催化剂高效合成了一系列新型复杂的环丁烷衍生物，即 1,2-二芳基-1,2-二氢吡啶-3,5-二羧酸二乙酯的二聚体。密度泛函理论和时间相关的密度泛函理论被用来阐明详细的反应过程，例如反应机理和环加成产物的立体选择性。