2-ethyl-5-(phenylmethyl)-3-furancarboxylic acid ethyl ester | 1309473-89-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 2-ethyl-5-(phenylmethyl)-3-furancarboxylic acid ethyl ester
• 英文别名: ethyl 5-benzyl-2-ethylfuran-3-carboxylate；Ethyl 5-benzyl-2-ethylfuran-3-carboxylate
• CAS: 1309473-89-9
• 化学式: C₁₆H₁₈O₃
• 分子量: 258.317
• InChiKey: VMAVQPXTMKQXEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  α-溴代肉桂醛 在 sodium tetrahydroborate 、 copper(l) iodide 、 溴 、 caesium carbonate 、 对苯二酚 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 2-ethyl-5-(phenylmethyl)-3-furancarboxylic acid ethyl ester
  参考文献：
  名称：

  2,3-Dihalo-1-propenes as Building Blocks in Cu(I)-Catalyzed Domino Reactions: Efficient and Selective Synthesis of Furans

  摘要：

  The Cu(I)-catalyzed reaction of 2,3-dibromo-1-propenes with beta-ketoesters and 1,3-diketones, respectively, in DMF at 120 degrees C using Cs2CO3 as a base and hydroquinone as an additive exclusively delivers 2,3,5-trisubstituted furans and related compounds with yields up to 96%. The highly regioselective domino process is based on an intermolecular C-allylation followed by an intramolecular Ullmann type O-vinylation and a double bond isomerization.

  DOI：

  10.1021/ol502371j

文献信息

• Furan synthesis through AuCl3-catalysed cycloisomerisation of β-alkynyl β-ketoesters
  作者：Arantxa Rodríguez、Wesley J. Moran

  DOI：10.1016/j.tetlet.2011.03.086

  日期：2011.5

  AuCl3 efficiently catalyses the cycloisomerisation of readily available beta-alkynyl beta-ketoesters to generate trisubstituted furans. The substrate scope is wide and the reaction is high yielding and operationally simple. (C) 2011 Elsevier Ltd. All rights reserved.
• 2,3-Dihalo-1-propenes as Building Blocks in Cu(I)-Catalyzed Domino Reactions: Efficient and Selective Synthesis of Furans
  作者：Dietmar Schmidt、Chandi C. Malakar、Uwe Beifuss

  DOI：10.1021/ol502371j

  日期：2014.9.19

  The Cu(I)-catalyzed reaction of 2,3-dibromo-1-propenes with beta-ketoesters and 1,3-diketones, respectively, in DMF at 120 degrees C using Cs2CO3 as a base and hydroquinone as an additive exclusively delivers 2,3,5-trisubstituted furans and related compounds with yields up to 96%. The highly regioselective domino process is based on an intermolecular C-allylation followed by an intramolecular Ullmann type O-vinylation and a double bond isomerization.