2-methyl-4H-1-benzopyran-3-carboxylic acid ethyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-methyl-4H-1-benzopyran-3-carboxylic acid ethyl ester
• 英文别名: ethyl 2-methyl-4H-chromene-3-carboxylate；2-Methyl-4h-chromene-3-carboxylic acid ethyl ester
• 化学式: C₁₃H₁₄O₃
• 分子量: 218.252
• InChiKey: DPRCYRVDNRJDRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-乙酰基-3-(2-溴苯基)丙酸乙酯 在 potassium phosphate 、 copper(I) bromide 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以65%的产率得到2-methyl-4H-1-benzopyran-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Assembly of 4H-chromenes, imidazobenzothiazines and quinazolines via copper-catalyzed domino reactions using 2-halobenzyl tosylates as substrates

  摘要：

  The use of 2-halobenzyl tosylates as substrates in copper-catalyzed domino intermolecular substitution/intramolecular arylation processes for the efficient and selective preparation of heterocycles is reported for the first time. Reaction of 2-halobenzyl tosylates with beta-ketoesters delivers 4H-chromenes with yields ranging between 59 and 89%. Imidazobenzothiazines are formed with yields up to 82% upon reaction of 2-halobenzyl tosylates with 2-mercaptoimidazoles. When 2-halobenzyl tosylates are reacted with benzamidines the corresponding quinazolines are obtained. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.06.071

文献信息

• An unusual Me₃SiI-promoted [4+2] annulation and reduction: an efficient approach to construct 4H-benzopyrans
  作者：Feijun Wang、Mingliang Qu、Feng Chen、Li Li、Min Shi

  DOI：10.1039/c1cc16028a

  日期：——

  Me3SiI-promoted reaction of salicylic aldehydes with β-dicarbonyl compounds provided a facile way to construct 4H-benzopyrans in moderate to good yields. This tandem reaction proceeds with high efficiency through nucleophilic addition, silyl enol ether formation, substitution, reduction, and intramolecular nucleophilic cyclization.

  Me3SiI-promoted reaction of salicylic aldehydes with β-dicarbonyl compounds provided a facile way to construct 4H-benzopyrans in moderate to good yields. This tandem reaction proceeds with high efficiency through nucleophilic addition, silyl enol ether formation, substitution, reduction, and intramolecular nucleophilic cyclization.
• Cu(I)-Catalyzed Domino Reactions: Efficient and Selective Synthesis of 4<i>H</i>-Chromenes and Naphthalenes
  作者：Chandi C. Malakar、Dietmar Schmidt、Jürgen Conrad、Uwe Beifuss

  DOI：10.1021/ol200347g

  日期：2011.4.15

  Depending on the ratio of the substrates and the reaction conditions, the Cu(I)-catalyzed domino reaction between bromobenzyl bromides and beta-ketoesters exclusively yields either 4H-chromenes or naphthalenes.
• O-Arylation versus C-Arylation:  Copper-Catalyzed Intramolecular Coupling of Aryl Bromides with 1,3-Dicarbonyls
  作者：Yewen Fang、Chaozhong Li

  DOI：10.1021/jo060747t

  日期：2006.8.1

  The copper-catalyzed intramolecular coupling of aryl bromides with 1,3-dicarbonyls via a six-membered ring closure was examined. With CuI (10 mol %) as the catalyst, N,N'-dimethylethylenediamine as the ligand, and Cs2CO3 as the base, the reactions of alpha-(2-bromobenzyl)-beta-keto esters in THF at refluxing temperature afforded the corresponding substituted 4H-1-benzopyrans in high yields via O-arylation. On the other hand, the reactions of delta-(2-bromophenyl)-beta-keto esters in refluxing dioxane led to the formation of 3,4-dihydronaphthalen-2(1H)-one derivatives via C-arylation.
• Assembly of 4H-chromenes, imidazobenzothiazines and quinazolines via copper-catalyzed domino reactions using 2-halobenzyl tosylates as substrates
  作者：Mohamed A. Omar、Jürgen Conrad、Uwe Beifuss

  DOI：10.1016/j.tet.2014.06.071

  日期：2014.9

  The use of 2-halobenzyl tosylates as substrates in copper-catalyzed domino intermolecular substitution/intramolecular arylation processes for the efficient and selective preparation of heterocycles is reported for the first time. Reaction of 2-halobenzyl tosylates with beta-ketoesters delivers 4H-chromenes with yields ranging between 59 and 89%. Imidazobenzothiazines are formed with yields up to 82% upon reaction of 2-halobenzyl tosylates with 2-mercaptoimidazoles. When 2-halobenzyl tosylates are reacted with benzamidines the corresponding quinazolines are obtained. (C) 2014 Elsevier Ltd. All rights reserved.