6-amino-5-cyano-2-methyl-4-(3-tolyl)-4H-pyran-3-carboxylic acid ethyl ester | 363592-26-1

• 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: 6-amino-5-cyano-2-methyl-4-(3-tolyl)-4H-pyran-3-carboxylic acid ethyl ester
• 英文别名: ethyl 6-amino-5-cyano-2-methyl-4-(3-methylphenyl)-4H-pyran-3-carboxylate
• CAS: 363592-26-1
• 化学式: C₁₇H₁₈N₂O₃
• 分子量: 298.342
• InChiKey: HYPHURACKKXCLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  85.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-甲基苯甲醛 在 ammonium acetate 作用下， 以 neat (no solvent) 为溶剂， 生成 6-amino-5-cyano-2-methyl-4-(3-tolyl)-4H-pyran-3-carboxylic acid ethyl ester
  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

• 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。
• Biocatalytic tandem multicomponent reactions for one-pot synthesis of 2-Amino-4H-Pyran library and in vitro biological evaluation
  作者：Zeng-Jie Yang、Qing-Tian Gong、Yun Wang、Yuan Yu、Yan-Hong Liu、Na Wang、Xiao-Qi Yu

  DOI：10.1016/j.mcat.2020.110983

  日期：2020.8

  methodology offers a mild approach to obtain a library of 2-amino-4H-pyrans with good yields and favorable function group tolerance. Moreover, molecular docking experiments have been carried out to investigate the possible mechanism of this enzyme-initiated one-pot reaction. In addition, eight compounds in the library have been chosen in order to evaluate the in vitro antitumor activities against three

  已开发出一种简单，有效且环保的生物催化方法，可在一锅中通过醛，丙二腈和乙酰乙酸乙酯的串联多组分反应（MCR）来构建2-氨基-4H-吡喃。研究了脂肪酶在不同反应介质和其他实验条件下的催化活性。报道的方法学提供了一种温和的方法来获得2-氨基-4H-吡喃的文库，具有良好的收率和良好的官能团耐受性。此外，已经进行了分子对接实验以研究这种酶引发的一锅反应的可能机理。此外，已选择文库中的八种化合物以评估针对三种细胞系（A549，Hela和HepG2）的体外抗肿瘤活性。结果表明4v具有最强的抗肿瘤活性，在A549细胞中IC50为0.0517μM。
• Diethylene glycol-bis(3-methylimidazolium) dihydroxide as a dicationic ionic liquid catalyst for the synthesis of 4H-pyrane derivatives in aqueous medium
  作者：Khodabakhsh Niknam、Mohsen Khataminejad、Fariba Zeyaei

  DOI：10.1016/j.tetlet.2015.12.034

  日期：2016.1

  Diethylene glycol-bis(3-methylimidazolium) dihydroxide [DiEG(mim)(2)[OH](2) was prepared by the reaction between sodium hydroxide and diethylene glycol-bis(3-methylimidazolium) dibromide in aqueous ethanol at room temperature. This solid, quaternized ionic liquid was employed as a recyclable catalyst for the synthesis of 4H-pyrane derivatives in high yields from the three-component condensation reaction of malononitrile, aromatic aldehydes, and 1,3-dicarbonyls in water at room temperature. In addition, spiropyrane derivatives were synthesized from the reaction of isatin, malononitrile, and 1,3-dicarbonyls in water at reflux. The dicationic ionic liquid showed the same efficiency when used in consecutive reactions. (C) 2015 Elsevier Ltd. All rights reserved.
• FIBROTIC TREATMENT
  申请人：Monash University

  公开号：US20180223287A1

  公开（公告）日：2018-08-09

  The present invention relates to a method for the treatment of fibrosis, in particular cardiac fibrosis, comprising the administration of an inhibitor of insulin-regulated aminopeptidase (IRAP). Preferable the IRAP inhibitor is chosen from the group including HFI-419, HA-08, AL-40, HFI-437, Val-Tyr-Ile-His-Pro-Phe (otherwise known as angiotensin IV or ANG IV), c[Cys-Tyr-Cys]-His-Pro-Phe, and c[Hcy-Tyr-Hcy]-His-Pro-Phe.
• Synthesis of 4<i>H</i>-Pyran Derivatives Under Solvent-Free and Grinding Conditions
  作者：Rufus Smits、Sergey Belyakov、Aiva Plotniece、Gunars Duburs

  DOI：10.1080/00397911.2012.716484

  日期：2013.1.1

  analysis, we have proved that the recently published results for ethyl 6-amino-5-cyano-4-aryl-1,4-dihydropyridine-3-carboxylate synthesis is in fact an environmentally friendly synthesis of 6-amino-5-cyano-4-aryl-4H-pyran derivatives using a multicomponent room-temperature grinding procedure of ethyl acetoacetate, [(2-aryl)methylene]malononitriles, and ammonium acetate. GRAPHICAL ABSTRACT

  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