ethyl 6-chloro-5-formyl-2-methyl-4-(2'-nitrophenyl)-1,4-dihydropyridine-3-carboxylate

• 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: ethyl 6-chloro-5-formyl-2-methyl-4-(2'-nitrophenyl)-1,4-dihydropyridine-3-carboxylate
• 英文别名: Ethyl 6-chloro-5-formyl-2-methyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3-carboxylate；ethyl 6-chloro-5-formyl-2-methyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3-carboxylate
• 化学式: C₁₆H₁₅ClN₂O₅
• 分子量: 350.759
• InChiKey: SMFOQDYWGQOQOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  邻苯二胺 、 ethyl 6-chloro-5-formyl-2-methyl-4-(2'-nitrophenyl)-1,4-dihydropyridine-3-carboxylate 在 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 8.5h， 以95%的产率得到3-(ethoxycarbonyl)-2-methyl-4-(2-nitrophenyl)-4,11-dihydro-1Hbenzo[b]pyrido[2,3-e][1,4]diazepin-6-ium chloride
  参考文献：
  名称：

  高效光学活性杂化1H-1,5-苯二氮杂-1,4-二氢吡啶类化合物的合成

  摘要：

  摘要 一系列光学活性杂化化合物，4-芳基-3-（乙氧羰基）-2-甲基-4,11-二氢-1 H-苯并[ b ]吡啶基[2,3- e ] [1,4]二氮杂-通过富含对映体的6-氯-5-甲酰基-1,4-二氢吡啶衍生物与苯之间的偶联反应已有效地合成了含有1 H -1,5-苯并二氮杂卓和1,4-二氢吡啶单元的6-盐-1,2-二胺 三氟乙酸的使用允许以非常高的产率获得相应的杂种。在该过程中未发生消旋。 一系列光学活性杂化化合物，4-芳基-3-（乙氧羰基）-2-甲基-4,11-二氢-1 H-苯并[ b ]吡啶基[2,3- e ] [1,4]二氮杂-通过富含对映体的6-氯-5-甲酰基-1,4-二氢吡啶衍生物与苯之间的偶联反应已有效地合成了含有1 H -1,5-苯并二氮杂卓和1,4-二氢吡啶单元的6-盐-1,2-二胺 三氟乙酸的使用允许以非常高的产率获得相应的杂种。在该过程中未发生消旋。

  DOI：

  10.1055/s-0035-1560409
• 作为产物：
  描述：

  邻硝基苯甲醛 在 丙二酸环(亚)异丙酯 、 溶剂黄146 、 三氯氧磷 作用下， 生成 ethyl 6-chloro-5-formyl-2-methyl-4-(2'-nitrophenyl)-1,4-dihydropyridine-3-carboxylate
  参考文献：
  名称：

  BENZODIAZEPINE PRODUCT WITH ACTIVITY ON THE CENTRAL NERVOUS AND VASCULAR SYSTEMS

  摘要：

  Formula III 化合物，其产物和含有它们的药物组合物，用于治疗中枢神经系统和血管系统疾病，特别是伴有认知恶化的神经退行性疾病，与氧化应激有关的疾病，涉及线粒体功能障碍的疾病，帕金森病和神经病性疼痛，以及与衰老有关的病理过程。

  公开号：

  US20190270738A1

文献信息

• Eco-Friendly Methodology to Prepare N-Heterocycles Related to Dihydropyridines: Microwave-Assisted Synthesis of Alkyl 4-Arylsubstituted-6-chloro-5-formyl-2-methyl-1,4-dihydropyridine-3-carboxylate and 4-Arylsubstituted-4,7-dihydrofuro[3,4-b]pyridine-2,5(1H,3H)-dione
  作者：Hortensia Rodríguez、Osnieski Martin、Margarita Suarez、Nazario Martín、Fernando Albericio

  DOI：10.3390/molecules16119620

  日期：——

  Here we describe the efficient synthesis of alkyl 4-arylsubstituted-6-chloro-5-formyl-2-methyl-1,4-dihydropyridine-3-carboxylates and 4-arylsubstituted-4,7-dihydro-furo[3,4-b]pyridine-2,5(1H,3H)-diones via microwave-accelerated reaction of alkyl 4-arylsubstituted-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxylates with the appropriate reagents. This eco-friendly approach to these valuable dihydropyridine derivatives does not involve the harsh or highly contaminating conditions common in classical heating and offers a reduction or even elimination of solvent use and recovery, simplification of the work-up procedures, facility of scale up, and low energy consumption, in addition to moderate to higher yields.

  本文描述了通过微波加速反应，高效合成烷基4-芳基取代-6-氯-5-甲酰基-2-甲基-1,4-二氢吡啶-3-羧酸酯和4-芳基取代-4,7-二氢-呋喃[3,4-b]吡啶-2,5(1H,3H)-二酮的方法。该环保合成途径不涉及传统加热中的苛刻或高度污染条件，减少了溶剂使用和回收，简化了后处理步骤，易于规模放大，能耗低，并且产率适中至较高。
• Efficient sonochemical synthesis of alkyl 4-aryl-6-chloro-5-formyl-2-methyl-1,4-dihydropyridine-3-carboxylate derivatives
  作者：Enrique Ruiz、Hortensia Rodríguez、Julieta Coro、Vladimir Niebla、Alfredo Rodríguez、Roberto Martínez-Alvarez、Hector Novoa de Armas、Margarita Suárez、Nazario Martín

  DOI：10.1016/j.ultsonch.2011.07.003

  日期：2012.3

  facile, efficient and environment-friendly protocol for the synthesis of 6-chloro-5-formyl-1,4-dihydropyridine derivatives has been developed by the convenient ultrasound-mediated reaction of 2(1H)pyridone derivatives with the Vilsmeier-Haack reagent. This method provides several advantages over current reaction methodologies including a simpler work-up procedure, shorter reaction times and higher yields

  通过2（1H）吡啶酮衍生物与Vilsmeier-Haack试剂的便捷超声介导反应，已开发出一种简便，高效且环境友好的合成6-氯-5-甲酰基-1,4-二氢吡啶衍生物的方案。 。与当前的反应方法相比，该方法具有多个优点，包括更简单的后处理步骤，更短的反应时间和更高的产率。
• Synthesis and study of novel fulleropyrrolidines bearing biologically active 1,4-dihydropyridines
  作者：Margarita Suárez、Yamila Verdecia、Beatriz Illescas、Roberto Martı́nez-Alvarez、Amaury Alvarez、Estael Ochoa、Carlos Seoane、Nour Kayali、Nazario Martı́n

  DOI：10.1016/j.tet.2003.09.047

  日期：2003.11

  New fulleropyrrolidines endowed with chlorine-containing biological active 1,4-dihydropyridines (1,4-DHPs) have been synthesised from the respective formyl substituted 1,4-DHPs by following Prato's procedure. The presence of the chlorine atom on C2 of the 1,4-DHP ring brings about important spectroscopical and structural differences in compounds 10a-f related to the parent hydrogen-containing 11a. The mass spectroscopy study reveals different fragmentation patterns for fulleropyrrolidines 10a-f and their precursors 1,4-DHPs, as well as with 11a. Semiempirical calculations (AMI and PM3) predict a most stable stereoisomer in all cases (RS for 10a-f) and the same RR for 11a. The presence of chlorine atom in 10a-f is responsible for the higher calculated conformational energy barriers in comparison with 11a. The geometry of:the 1,4-DHP shows that the presence of fullerene unit does not significantly alter the required conformation for biological activity. (C) 2003 Elsevier Ltd. All rights reserved.
• US20140275042A1
  申请人：——

  公开号：US20140275042A1

  公开（公告）日：2014-09-18
• BENZODIAZEPINE PRODUCT WITH ACTIVITY ON THE CENTRAL NERVOUS AND VASCULAR SYSTEMS
  申请人：UNIVERSIDAD DE LA HABANA

  公开号：US20190270738A1

  公开（公告）日：2019-09-05

  Formula III compound, its products and pharmaceutical compositions containing them for the treatment of central nervous and vascular system diseases, particularly neurodegenerative disorders with cognitive deterioration, diseases associated with oxidative stress, diseases taking in mitochondrial dysfunction, Parkinson's disease and neuropathic pain, as well as the pathological processes associated with aging.

  Formula III 化合物，其产物和含有它们的药物组合物，用于治疗中枢神经系统和血管系统疾病，特别是伴有认知恶化的神经退行性疾病，与氧化应激有关的疾病，涉及线粒体功能障碍的疾病，帕金森病和神经病性疼痛，以及与衰老有关的病理过程。