2-But-3-enyl-4H-chromene-3-carboxylic acid methyl ester | 909190-72-3

• 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-But-3-enyl-4H-chromene-3-carboxylic acid methyl ester
• 英文别名: Methyl 2-(3-buten-1-yl)-4H-1-benzopyran-3-carboxylate；methyl 2-but-3-enyl-4H-chromene-3-carboxylate
• CAS: 909190-72-3
• 化学式: C₁₅H₁₆O₃
• 分子量: 244.29
• InChiKey: ZQAZZDVPPLJNIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 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-(2-Bromo-benzyl)-3-oxo-hept-6-enoic acid methyl ester 在 copper(l) iodide 、 caesium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以92%的产率得到2-But-3-enyl-4H-chromene-3-carboxylic acid methyl ester
  参考文献：
  名称：

  O-Arylation versus C-Arylation:  Copper-Catalyzed Intramolecular Coupling of Aryl Bromides with 1,3-Dicarbonyls

  摘要：

  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.

  DOI：

  10.1021/jo060747t

文献信息

• 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.