2-amino-4-(4-methylphenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylic acid ethyl ester | 349492-09-7

• 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: 2-amino-4-(4-methylphenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylic acid ethyl ester
• 英文别名: ethyl 2-amino-4-(4-methylphenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate；ethyl 2-amino-4-(4-methylphenyl)-5-oxo-4,6,7,8-tetrahydrochromene-3-carboxylate
• CAS: 349492-09-7
• 化学式: C₁₉H₂₁NO₄
• 分子量: 327.38
• InChiKey: XFXUXGOVHIPUKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  78.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  对甲基苯甲醛 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 生成 2-amino-4-(4-methylphenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis of Substituted Tetrahydrochromenes by the Reactions of α,β-Unsaturated Cyanoesters with Dimedone/1,3-Cyclohexanedione

  摘要：

  Ethyl esters of 2-cyano-3-arylacrylic acid 1a-d (a=4-CH3-C6H4-, b=4-N(CH3)(2)-C6H4-, c=2-CH3O-C6H4-, d=2-Cl-C6H4-) reacted with 5,5-dimethyl-1,3-cyclohexanedione (2p, Y=CH3), and 1e-g (e=4-CH3-C6H4-, f=2-CH3O-C6H4-, g=2-Cl-C6H4-) reacted with 1,3-cyclohexanedione (2q, Y=H) in the presence of alcoholic sodium ethoxide to give the corresponding ethyl esters of 2-amino-7,7-dimethyl-5-oxo-4-aryl-5,6,7,8-tetrahydro-4H-chromene-3-carboxylic acid 4a-d and 2-amino-5-oxo-4-aryl-5,6,7,8-tetrahydro-4H-chromene-3-carboxylic acid 4e-g. The structures of the compounds 4a-g were confirmed by their ultraviolet, infrared, H-1 NMR, C-13 NMR, and mass spectral data and elemental analyses.

  DOI：

  10.1080/00397911.2010.515346

文献信息

• Practical and efficient synthesis of tetrahydrobenzo[b]pyran using caffeine supported on silica as an ionic liquid solid acid catalyst
  作者：Mohammad Bakherad、Ali Keivanloo、Elmira Moradian、Amir H. Amin、Rahele Doosti、Mahsa Armaghan

  DOI：10.1007/s13738-018-1468-y

  日期：2018.12

  The catalyst prepared was then characterized by the FT-IR spectroscopy, TGA, EDX, and SEM techniques. It was found that this heterogeneous catalyst was a highly efficient one for the synthesis of tetrahydrobenzo[b]pyrans in good-to-high yields, and could be recovered by a simple filtration of the reaction solution and reused for five consecutive runs. The attractive features of this method are simple

  新型催化剂二氧化硅-咖啡因硫酸氢盐[SiO 2 -caff。] HSO 4可以方便地由市售的3-氯丙基三乙氧基硅烷固定在二氧化硅上，然后与咖啡因反应制得。然后通过FT-IR光谱，TGA，EDX和SEM技术表征制备的催化剂。发现该非均相催化剂是用于以高至高收率合成四氢苯并[ b ]吡喃的高效催化剂，并且可以通过简单过滤反应溶液进行回收并将其重复使用五次。该方法的吸引人的特征是操作简单，反应干净，后处理容易，使用可重复使用的催化剂以及进行多组分反应。
• Synthesis of Substituted Tetrahydrochromenes by the Reactions of α,β-Unsaturated Cyanoesters with Dimedone/1,3-Cyclohexanedione
  作者：M. Giasuddin Ahmed、U. K. R. Romman、Kawsari Akhter、Khorshada Jahan、M. Nazmul Hasan Bhuiyan、M. Ershad Halim

  DOI：10.1080/00397911.2010.515346

  日期：2011.10

  Ethyl esters of 2-cyano-3-arylacrylic acid 1a-d (a=4-CH3-C6H4-, b=4-N(CH3)(2)-C6H4-, c=2-CH3O-C6H4-, d=2-Cl-C6H4-) reacted with 5,5-dimethyl-1,3-cyclohexanedione (2p, Y=CH3), and 1e-g (e=4-CH3-C6H4-, f=2-CH3O-C6H4-, g=2-Cl-C6H4-) reacted with 1,3-cyclohexanedione (2q, Y=H) in the presence of alcoholic sodium ethoxide to give the corresponding ethyl esters of 2-amino-7,7-dimethyl-5-oxo-4-aryl-5,6,7,8-tetrahydro-4H-chromene-3-carboxylic acid 4a-d and 2-amino-5-oxo-4-aryl-5,6,7,8-tetrahydro-4H-chromene-3-carboxylic acid 4e-g. The structures of the compounds 4a-g were confirmed by their ultraviolet, infrared, H-1 NMR, C-13 NMR, and mass spectral data and elemental analyses.