ethyl 6-amino-5-cyano-2-methyl-4-(3-nitrophenyl)-4H-pyran-3-carboxylate | 72568-54-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 6-amino-5-cyano-2-methyl-4-(3-nitrophenyl)-4H-pyran-3-carboxylate
• 英文别名: 6-amino-5-cyano-2-methyl-4-(3-nitro-phenyl)-4H-pyran-3-carboxylic acid ethyl ester；6-amino-5-cyano-2-methyl-4-(3-nitrophenyl)-4H-pyran-3-carboxylic acid ethyl ester；2-amino-5-ethoxycarbonyl-6-methyl-4-(3-nitrophenyl)-4H-pyrano-3-carbonitrile；ethyl-6-amino-5-cyano-2-methyl-4-(3-nitrophenyl)-4H-pyran-3-carboxylate；5-ethoxycarbonyl-2-amino-4-(3-nitrophenyl)-3-cyano-6-methyl-4H-pyran；ethyl 6-amino-5-cyano-2-methyl-4-(3-nitrophenyl)-4H-pyrano-3-carboxylate
• CAS: 72568-54-8
• 化学式: C₁₆H₁₅N₃O₅
• 分子量: 329.312
• InChiKey: OWNUPBHMJRSEAG-UHFFFAOYSA-N

物化性质

• 熔点：
  182-183 °C(Solv: methanol (67-56-1))
• 沸点：
  553.0±50.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  131
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 6-amino-5-cyano-2-methyl-4-(3-nitrophenyl)-4H-pyran-3-carboxylate 在 乙酸铵 、 三氯化铝 、 溶剂黄146 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 5-amino-2-methyl-4-(3-nitro-phenyl)-7,8,9,10-tetrahydro-6H-cyclohepta[b][1,8]naphthyridine-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis, biological evaluation and molecular modelling of diversely functionalized heterocyclic derivatives as inhibitors of acetylcholinesterase/butyrylcholinesterase and modulators of Ca2+ channels and nicotinic receptors

  摘要：

  The synthesis and the biological activity of compounds 5-40 as inhibitors of acetyleholinesterase (AChE) and butyrylcholinesterase (BuChE), as well as modulators of voltage-dependent Ca2+ channels and nicotinic receptors, are described. These molecules are tacrine analogues, which have been prepared from polyfunctionalized 6-amino-5-cyano-4H-pyrans, 6-amino-5-cyano-pyridines and 5-amino-2-aryl-3-cyano-1,3-oxazoles via Friedlander reaction with selected cycloalkanones. These compounds are moderate acetylcholinesterase and butyrylcholinesterase inhibitors, the BuChE/AChE selectivity of the most active molecules ranges from 10.0 (compound 29) to 76.9 (compound 16). Interestingly, the 'oxazolo-tacrine' derivatives are devoid of any activity. All compounds showed an important inhibitory effect on the nicotinic acetylcholine receptor. Most of them also blocked L-type Ca2+ channels, and three of them, 64, 19 and 67, the non-L type of Ca2+ channels. Molecular modelling studies suggest that these compounds might bind at the peripheral binding site of AChE, which opens the possibility to design inhibitors able to bind at both, the catalytic and peripheral binding sites of the enzyme. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.02.017
• 作为产物：
  描述：

  间硝基苯甲醛 在 ammonium acetate 作用下， 以 neat (no solvent) 为溶剂， 生成 ethyl 6-amino-5-cyano-2-methyl-4-(3-nitrophenyl)-4H-pyran-3-carboxylate
  参考文献：
  名称：

  无溶剂研磨条件下4H-吡喃衍生物的合成

  摘要：

  摘要 基于 X 射线衍射分析，我们证明最近发表的 6-amino-5-cyano-4-aryl-1,4-dihydropyridine-3-carboxylate 合成结果实际上是 6-amino-5-cyano-4-aryl-1,4-dihydropyridine-3-carboxylate 的环保合成。 -氨基-5-氰基-4-芳基-4H-吡喃衍生物，使用乙酰乙酸乙酯、[(2-芳基)亚甲基]丙二腈和乙酸铵的多组分室温研磨程序。图形概要

  DOI：

  10.1080/00397911.2012.716484

文献信息

• One-pot synthesis of some 2-amino-4H-chromene derivatives using triethanolamine as a novel reusable organocatalyst under solvent-free conditions and its application in electrosynthesis of silver nanoparticles
  作者：B. Maleki、M. Baghayeri、S. Sheikh、S. Babaee、S. Farhadi

  DOI：10.1134/s1070363217050280

  日期：2017.5

  2-amino-4H-chromene derivatives. Its advantages include short reaction time, high yields, low cost, and straightforward work-up. Triethanolamine is an efficient reusable catalyst. 2-Amino-4H-benzo[g]chromenes (ABgC) were applied as novel components of electro synthesis of silver nanoparticles.

  通过芳族醛和丙二腈与2-羟基萘-1,4-二酮的一锅三组分反应，有效地制备了在4 H-色烯环上具有不同取代基的各种2-氨基-4 H-色烯衍生物在无溶剂条件下，在三乙醇胺存在下作为乙酰乙酸乙酯或萘酚作为一种新的有机催化剂。该方法是无过渡金属的且对各种2-氨基-4 H-色烯衍生物无害于环境的方法。其优点包括反应时间短，产率高，成本低和后处理简单。三乙醇胺是一种有效的可重复使用的催化剂。2-氨基-4 H-苯并[ g对苯二甲腈（ABgC）被用作银纳米粒子电合成的新型组分。
• One-pot synthesis of 2-amino-3-cyano-4<i>H</i>-pyrans and pyran-annulated heterocycles using sodium citrate as an organo-salt based catalyst in aqueous ethanol
  作者：Aiborlang Thongni、Pynskhemborlang T. Phanrang、Arup Dutta、Rishanlang Nongkhlaw

  DOI：10.1080/00397911.2021.1998535

  日期：2022.1.2

  shorter reaction time, utilization of eco-friendly solvents, operational simplicity, mild reaction conditions, and maximum product yield. Moreover, the use of sodium citrate as an easily available, cheap and benign catalyst plays a pivotal role from a green perspective, considering its high recyclability and easy recovery. Therefore, this present methodology offers numerous possibilities in terms of large-scale

  摘要 柠檬酸钠作为一种高效催化剂被开发用于合成官能化的 2-氨基-3-氰基-4 H-吡喃和吡喃环化杂环。该方法涉及芳香醛、丙二腈和 1,3-二羰基化合物与 EtOH 的一锅三组分反应：H 2O (1:1 v/v) 在室温下作为溶剂。该协议具有几个优点，例如更短的反应时间、环保溶剂的利用、操作简单、反应条件温和和产品收率最高。此外，考虑到柠檬酸钠的高可回收性和易回收性，从绿色角度来看，柠檬酸钠作为一种易于获得、廉价和良性的催化剂发挥着关键作用。因此，本方法在大规模工业合成或应用于众多有机转化方面提供了许多可能性。此外，还对产物4aa形成的机理途径进行了理论研究，以确定柠檬酸钠对DFT法反应可行性的催化作用，使用B3LYP泛函。
• Silica-bonded N-propylpiperazine sodium n-propionate as recyclable catalyst for synthesis of 4H-pyran derivatives
  作者：Khodabakhsh Niknam、Nassim Borazjani、Reza Rashidian、Abbas Jamali

  DOI：10.1016/s1872-2067(12)60693-7

  日期：2013.12

  the preparation of a series of 4 H -benzo[b]pyran derivatives. SBPPSP was used as a recyclable heterogeneous solid base catalyst for the synthesis of 3,4-dihydropyrano[c]chromenes, 2-amino-4 H -pyrans, 1,4-dihydropyrano[2,3-c]pyrazoles, and 2-amino-4 H -benzo[e]-chromenes via the condensation reaction of dimedone, ethyl acetoacetate, 3-methyl-1-phenyl-1 H -pyrazol-5(4 H )-one, and α-naphthol, respectively

  摘要 二氧化硅键合的 N-丙基哌嗪正丙酸钠 (SBPPSP) 被发现是制备一系列 4 H-苯并[b]吡喃衍生物的有效固体碱。SBPPSP 用作可回收的多相固体碱催化剂，用于合成 3,4-二氢吡喃并[c]色烯、2-氨基-4 H-吡喃、1,4-二氢吡喃并[2,3-c]吡唑和 2-氨基-4 H-苯并[e]-色烯分别通过二甲酮、乙酰乙酸乙酯、3-甲基-1-苯基-1 H-吡唑-5(4 H)-酮和α-萘酚的缩合反应，与芳香醛和丙二腈在回流的乙醇水溶液中。多相固体碱在连续反应中重复使用时表现出相似的效率。
• Organocatalytic mediated green approach: A versatile new <scp>L</scp>-valine promoted synthesis of diverse and densely functionalized 2-amino-3-cyano-4H-pyrans
  作者：Jyoti Tiwari、Swastika Singh、Mohammad Saquib、Fatima Tufail、Amit Kumar Sharma、Shailesh Singh、Jaya Singh、Jagdamba Singh

  DOI：10.1080/00397911.2017.1393087

  日期：2018.1.17

  new L-valine promoted facile and versatile green synthesis of diversified 2-amino-3-cyano-4H-pyrans using a one pot multicomponent-tandem reaction of aromatic aldehydes, malononitrile, and diverse electron-rich enolizable carbonyl compounds is described. To the best of our knowledge this is the first report on the use of native L-valine as a catalyst in organic synthesis. Environmental friendly, mild

  摘要：新型 L-缬氨酸的发现促进了多种 2-氨基-3-氰基-4H-吡喃的简便、多功能绿色合成，使用芳香醛、丙二腈和多种富电子可烯醇化羰基化合物的单锅多组分串联反应被描述。据我们所知，这是关于在有机合成中使用天然 L-缬氨酸作为催化剂的第一份报告。环境友好、反应条件温和、使用容易获得的廉价原料、反应时间短、产率高、原子经济性高和有机催化剂的可回收性是所公开方案的主要优点。图形概要
• Tetramethylguanidine-[bmim][BF4]. An Efficient and Recyclable Catalytic System for One-Pot Synthesis of 4H-Pyrans
  作者：Yanqing Peng、Gonghua Song、Feifei Huang

  DOI：10.1007/s00706-004-0270-y

  日期：2005.5

  A clean and efficient method for the synthesis of 4 H -pyran derivatives through the one-pot condensation of aromatic aldehydes, malononitriles, and β-dicarbonyl compounds, using guanidine base tetramethylguanidine in [ bmim ][BF4] ionic liquid as a recyclable catalytic system, was described.

  一种清洁有效的方法，通过在[ bmim ] [BF 4 ]离子液体中使用胍基四甲基胍作为可循环使用的催化剂，通过芳族醛，丙二腈和β-二羰基化合物的一锅缩合来合成4 H- 吡喃衍生物 系统，进行了描述。