ethyl 5-(4-(tert-butyl)phenyl)-2-methylfuran-3-carboxylate | 925459-42-3

• 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-(4-(tert-butyl)phenyl)-2-methylfuran-3-carboxylate
• 英文别名: Ethyl 5-(4-tert-butylphenyl)-2-methylfuran-3-carboxylate；ethyl 5-(4-tert-butylphenyl)-2-methylfuran-3-carboxylate
• CAS: 925459-42-3
• 化学式: C₁₈H₂₂O₃
• 分子量: 286.371
• InChiKey: FCLNQKFLOCTICS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 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：

  4-叔-丁基苯基乙炔 、 乙酰乙酸乙酯 在 potassium acetate 、 silver carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以60%的产率得到ethyl 5-(4-(tert-butyl)phenyl)-2-methylfuran-3-carboxylate
  参考文献：
  名称：

  Silver-Mediated Oxidative C–H/C–H Functionalization: A Strategy To Construct Polysubstituted Furans

  摘要：

  A novel silver-mediated highly selective oxidative C-H/C-H functionalization of 1,3-dicarbonyl compounds with terminal alkynes for the creation of polysubstituted furans and pyrroles in one step has been demonstrated. Promoted by the crucial silver species, perfect selectivity and good to excellent yields could be achieved. This protocol represents an extremely simple and atom-economic way to construct polysubstituted furans and pyrroles from basic starting materials under mild conditions.

  DOI：

  10.1021/ja301153k

文献信息

• Cu(I)-catalyzed reaction of diazo compounds with terminal alkynes: a direct synthesis of trisubstituted furans
  作者：Mohammad Lokman Hossain、Fei Ye、Yan Zhang、Jianbo Wang

  DOI：10.1016/j.tet.2014.07.086

  日期：2014.9

  method for the synthesis of tri-substituted furans has been developed based on Cu(I)-catalyzed reaction of terminal alkynes with β-keto α-diazoesters. This method for the synthesis of 2,3,5-trisubstituted furans is operationally simple and applicable to wide substrate scope. Moreover, this synthesis employs cheap Cu(MeCN)4PF6 as the catalyst and no additional ligand is needed. Similar reaction has also been

  基于Cu（I）催化的末端炔烃与β-酮α-重氮酸酯的反应，已经开发了一种三取代呋喃的合成方法。该合成2,3,5-三取代呋喃的方法操作简单，适用于广泛的底物范围。此外，该合成采用廉价的Cu（MeCN）4 PF 6作为催化剂，不需要其他配体。类似的反应也已用于（E）-2-重氮-3-（甲氧基亚氨基）丁酸乙酯，用于合成2,3,5-三取代的N-甲氧基吡咯，但效果有限。
• Synthesis of Furans via Rhodium(III)-Catalyzed Cyclization of Acrylic Acids with α-Diazocarbonyl Compounds
  作者：Chao Hong、Shuling Yu、Zhanxiang Liu、Zijing Xu、Yuhong Zhang

  DOI：10.1021/acs.joc.2c00924

  日期：2022.9.16

  An efficient protocol for the synthesis of furans through Rh(III)-catalyzed vinyl C–H activation from acrylic acids and α-diazocarbonyl compounds has been developed. The reaction features broad functional group tolerance and affords a series of furans in moderate to good yields. Moreover, no additives such as copper or silver salts are required. Some control experiments are performed to give insight

  已经开发了一种通过 Rh(III) 催化的丙烯酸和 α-重氮羰基化合物的乙烯基 C-H 活化合成呋喃的有效方案。该反应具有广泛的官能团耐受性，并以中等至良好的产率提供了一系列呋喃。此外，不需要诸如铜盐或银盐之类的添加剂。进行了一些对照实验以深入了解这种级联转化的机制，并且脱羰过程涉及呋喃产物的形成。