diethyl 4-(3,4,5-trimethoxylphenyl)-1,4-dihydropyridine-3,5-dicarboxylate | 120533-65-5

• 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-(3,4,5-trimethoxylphenyl)-1,4-dihydropyridine-3,5-dicarboxylate
• 英文别名: diethyl 4-(3,4,5-trimethoxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylate
• CAS: 120533-65-5
• 化学式: C₂₀H₂₅NO₇
• 分子量: 391.421
• InChiKey: FHUYWUZABQVMPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  92.3
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  diethyl 4-(3,4,5-trimethoxylphenyl)-1,4-dihydropyridine-3,5-dicarboxylate 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 tetraethyl 6,12-bis(3,4,5-trimethoxylphenyl)-3,9-diazahexacyclo[6.4.0.0^2,7.0^4,11.0^5,10]dodecane-1,5,7,11-tetracarboxylate
  参考文献：
  名称：

  操纵γ-环糊精中1,4-二氢吡啶的[2 + 2]光二聚化

  摘要：

  在γ-环糊精（γ -CD）存在下照射1,4-二氢吡啶（DHP）可以在中压汞灯下有效形成笼状二聚体。γ -CD中复合的DHP的笼二聚体产率可达到约80％，远高于非复合状态的DHP 。假设可用的腔体体积为γ-CD负责观察到的选择性。1：2宿主-客体包含复合物的形成在此反应中起重要作用，并按预期操作DHP进行[2 + 2]光二聚。为了研究包含过程，研究了光谱特征，并使用密度泛函理论（DFT）进行了理论研究。

  DOI：

  10.1016/j.jphotochem.2018.03.046
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲醛 、 丙炔酸乙酯 在 ammonium acetate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以83%的产率得到diethyl 4-(3,4,5-trimethoxylphenyl)-1,4-dihydropyridine-3,5-dicarboxylate
  参考文献：
  名称：

  1,4-二氢吡啶的高度区域选择性光二聚化：新型3,6-二氮杂四硬脂烷的有效合成

  摘要：

  传统的1，4-二氢吡啶的光环加成不能提供新颖的头对头的3，6-二氮杂四硬脂烷。在这里，我们描述了一种高度区域选择性的方法，通过1，4-二氢吡啶的分子内光二聚作用来合成3,6-二氮杂四环烷。首先，通过邻苯二甲酰基将1,4-二氢吡啶束缚在一起，以通过C的旋转在头对头方向上指导近似的平行排列溶液中的C单键。随后进行分子内[2 + 2]光环加成反应，以高收率（92–97％）和优异的区域选择性得到所需的3,6-二氮杂四硬脂烷。此外，两种不同的1,4-二氢吡啶也可以通过这种策略进行区域控制，并以简洁有效的方式通过交叉光二聚化产生多取代的3,6-二氮杂四硬脂烷。另外，该方法可以提供从1，4-二氢吡啶类似物直接进入其他多取代的多面体支架的途径。

  DOI：

  10.1016/j.tet.2017.10.019

文献信息

• 一种氮杂四星烷类化合物的可见光制备方法
  申请人：北京工业大学

  公开号：CN111362941A

  公开（公告）日：2020-07-03

  一种氮杂四星烷类化合物的可见光制备方法，属于有机化合物合成技术领域。本发明所提供的氮杂四星烷类化合物，其中环1和环2中的X至少同时有一个为氮原子，另一个为碳原子，包括以下步骤：以1,4‑二氢吡啶衍生物或/和1,4‑二氢吡嗪衍生物为反应底物，和可见光催化剂溶解在溶剂中，置于可见光照射下，发生[2+2]光环合反应。此方法具有合成路线简单、操作简便、化学选择性高、产率高以及绿色环保和节能洁净等的优点。
• Hetero-intermolecular [2+2] photocycloaddition of 1,4-dihydropyridines: a combined experimental and DFT study
  作者：Qiangwen Fan、Hongbo Tan、Peng Li、Hong Yan

  DOI：10.1039/c8nj02192a

  日期：——

  In this article, the hetero-intermolecular [2+2] photocycloaddition of 1,4-dihydropyridines (1,4-DHPs) in solution was reported, wherein head-to-tail (HT) dimeric products (syn-dimers and cage dimers) were formed exclusively through successive inter- and intra-molecular [2+2] cycloaddition. The effects of irradiation wavelength, solvents and substituents on the efficiency of these transformations were

  在本文中，在异质的分子间[2 + 2]的溶液中1,4-二氢吡啶（1,4-DHP类）光环被报道，其特征在于，头-尾（HT）的二聚产物（顺式-dimers和笼二聚体）仅通过连续的分子间和分子内[2 + 2]环加成反应形成。研究了辐照波长，溶剂和取代基对这些转化效率的影响。为了阐明光环加成反应的内在特征和立体选择性，进行了DFT和TDDFT理论计算，以揭示详细的反应过程。
• Molecular structure, spectroscopic and DFT computational studies on 3,9-diazatetraasteranes
  作者：Runzhi Sun、Yeming Wang、Changwei Ge、Shijie Wang、Xiuqing Song、Hong Yan

  DOI：10.1007/s11696-022-02645-8

  日期：——

  The molecular structure was of great significance on the unique physical and chemical properties that closely related to pharmacological applications, especially the cage-like hydrocarbons. The 3,9-diazatetraasterane derivatives were cage-like hydrocarbons and had been extensively studied because of the HIV-1 inhibitor activity and anti-tumor activity. C2-3,9-Diazatetraasterane was a self-dimer of

  分子结构对与药理应用密切相关的独特理化性质具有重要意义，尤其是笼状烃。3,9-二氮杂四星烷衍生物是笼状碳氢化合物，由于具有 HIV-1 抑制剂活性和抗肿瘤活性，已被广泛研究。C 2 -3,9-二氮杂四星烷是1,4-二氢吡啶的自二聚体，非C 2-3,9-二氮杂四甾烷是不同的1,4-二氢吡啶的交叉二聚体。为了讨论两种类型的 3,9-二氮杂四星烷对 NMR 的空间影响，通过信号的移动和分配详细地进行了 1D-NMR 和 2D-​​NMR 分析。单晶 X 射线衍射 (XRD) 进一步阐明了非C 2对称性对 3,9-二氮杂四星烷中心笼几何形状的影响。进行了前沿分子轨道 (FMO)、静电势 (ESP) 和激发态几何分析，以深入了解笼状结构的分子特征。
• Triplet phenacylimidazoliums-catalyzed photocycloaddition of 1,4-dihydropyridines: An experimental and theoretical study
  作者：Xiaohe Zhu、Weipeng Li、Hong Yan、Rugang Zhong

  DOI：10.1016/j.jphotochem.2012.05.013

  日期：2012.8

  The photocycloadditions of 1,4-dihydropyridines (DHPs) were achieved by using phenacylimidazoliums (Plms) as photosensitizers. Irradiation of DHPs 3a-g in the presence of Plms 1a-e and 2 performed an efficient formation of 3,9-diazatetraasteranes in shorter times under a lower power lamp. The mechanism of photocycloaddition catalyzed by Plm was studied by laser flash photolysis and theoretical OFT computation. These time-resolved results showed that the triplet excited states of Plms were generated with high efficiency and detected by their characteristic ultraviolet absorptions, which were quenched by DHP at almost diffusion controlled rate. Theoretical studies suggest that Plm is involved in the photocycloaddition process through the (3)(DHP center dot center dot center dot Plm)* triplet complexes and assists the stabilization of intermediates. All subsequent steps are predicted to be favorable and exothermic, leading to the cage dimers. (C) 2012 Elsevier B.V. All rights reserved.
• Design, Synthesis and Biological Evaluation of 3,9-diazatetraasteranes as Novel Matrilysin Inhibitors
  作者：Yanlan Liu、Hongbo Tan、Hong Yan、Xiuqing Song

  DOI：10.1111/cbdd.12185

  日期：2013.11

  Matrilysin is an ideal biological target to develop novel inhibitors because it is overexpressed in malignant tumour cells. A series of 3,9‐diazatetraasteranes was designed as inhibitors of matrilysin, which was an ideal biological target because it is responsible for aggressive malignant phenotypes and poor prognoses implicated in many cancers. Docking simulation supported the initial pharmacophore hypothesis and suggested a common interaction mechanism of 3,9‐diazatetraasteranes with the catalytic site of matrilysin. The 3,9‐diazatetraasteranes were synthesized by the photocyclization of 4‐aryl‐1,4‐dihydropyridines, and their structures were determined using 1H NMR, 13C NMR and MS. The inhibitory activities of these compounds on matrilysin were investigated in vitro using an MTT assay in A549 (small cell lung cancer) cells. The results show that the 3,9‐diazatetraasteranes can inhibit the growth of A549 tumour cells. The best IC50 value is approximately 50 μm. This result indicates that 3,9‐diazatetraasteranes will be useful pharmacological tools for the investigation of matrilysin inhibitors.