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