ethyl 5-benzyl-2-methylfuran-3-carboxylate | 24115-80-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: ethyl 5-benzyl-2-methylfuran-3-carboxylate
• CAS: 24115-80-8
• 化学式: C₁₅H₁₆O₃
• 分子量: 244.29
• InChiKey: YLAUHKOIVVQHFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 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：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  α-bromo cinnamyl alcohol 在 copper(l) iodide 、 溴 、 caesium carbonate 、 对苯二酚 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 ethyl 5-benzyl-2-methylfuran-3-carboxylate
  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

• Palladium-Catalyzed Oxidative Cycloisomerization of 2-Cinnamyl-1,3-Dicarbonyls: Synthesis of Functionalized 2-Benzyl Furans
  作者：Rajender Nallagonda、Reddy Rajasekhar Reddy、Prasanta Ghorai

  DOI：10.1002/chem.201502781

  日期：2015.10.12

  A new palladium‐catalyzed intramolecular oxidative cycloisomerization of readily available starting materials, 2‐cinnamyl‐1,3‐dicarbonyls, has been demonstrated for the creation of structurally diverse 2‐benzyl furans. The cycloisomerization occurs by a regioselective 5‐exo‐trig pathway. The reaction shows a broad substrate scope with good to excellent yields. Furthermore, a one‐pot procedure has been

  新型钯催化的分子内氧化环化异构反应可轻松获得，即2-肉桂基-1,3-二羰基原料，可用于形成结构多样的2-苄基呋喃。环异构化是通过区域选择性5 exo- trig途径进行的。该反应显示出广泛的底物范围，具有良好至优异的产率。此外，通过使用现成的肉桂醇和1,3-二酮，可以执行一锅法。
• Palladium-Catalyzed One-Pot Synthesis of Highly Substituted Furans by a Three-Component Annulation Reaction
  作者：Xin-hua Duan、Xue-yuan Liu、Li-na Guo、Meng-chun Liao、Wei-Min Liu、Yong-min Liang

  DOI：10.1021/jo050908d

  日期：2005.8.1

  A new three-component cyclization−coupling reaction catalyzed by palladium was developed, producing polysubstituted furans in good yields from readily available substrates. The reaction conditions and the scope of the process were examined, and a possible mechanism is proposed.

  开发了一种新的由钯催化的三组分环化偶联反应，可从容易获得的底物中以高收率生产多取代的呋喃。研究了反应条件和反应范围，并提出了可能的机理。