ethyl 5-acetamido-2-methyl-5-phenyl-4,5-dihydrofuran-3-carboxylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 5-acetamido-2-methyl-5-phenyl-4,5-dihydrofuran-3-carboxylate
• 英文别名: ethyl 2-acetamido-5-methyl-2-phenyl-3H-furan-4-carboxylate
• 化学式: C₁₆H₁₉NO₄
• 分子量: 289.331
• InChiKey: DPPNDBJAGZVHAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 5-acetamido-2-methyl-5-phenyl-4,5-dihydrofuran-3-carboxylate 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以95%的产率得到乙基2-甲基-5-苯基-3-糠酸酯
  参考文献：
  名称：

  Direct Oxidative Coupling of Enamides and 1,3-Dicarbonyl Compounds: A Facile and Versatile Approach to Dihydrofurans, Furans, Pyrroles, and Dicarbonyl Enamides

  摘要：

  An efficient manganese(III)-mediated oxidative coupling reaction between a-aryl enamides and 1,3-dicarbonyl compounds has been developed. A series of dihydrofurans and dicarbonyl enamides were synthesized in moderate to good yields. Moreover, these dihydrofurans could be readily transformed into the corresponding furans and pyrroles via the Paal-Knorr reaction.

  DOI：

  10.1021/ol503009f
• 作为产物：
  描述：

  苯乙酮肟 在 copper(l) iodide 、 manganese(III) triacetate dihydrate 、 碳酸氢钠 作用下， 以 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 6.0h， 生成 ethyl 5-acetamido-2-methyl-5-phenyl-4,5-dihydrofuran-3-carboxylate
  参考文献：
  名称：

  Direct Oxidative Coupling of Enamides and 1,3-Dicarbonyl Compounds: A Facile and Versatile Approach to Dihydrofurans, Furans, Pyrroles, and Dicarbonyl Enamides

  摘要：

  An efficient manganese(III)-mediated oxidative coupling reaction between a-aryl enamides and 1,3-dicarbonyl compounds has been developed. A series of dihydrofurans and dicarbonyl enamides were synthesized in moderate to good yields. Moreover, these dihydrofurans could be readily transformed into the corresponding furans and pyrroles via the Paal-Knorr reaction.

  DOI：

  10.1021/ol503009f

文献信息

• Facile Synthesis of Trisubstituted Carbazoles by Acid‐Catalyzed Ring‐Opening Annulation of 2‐Amidodihydrofurans with Indoles
  作者：Jingjing Zhao、Pan Li、Chungu Xia、Fuwei Li

  DOI：10.1002/chem.201503260

  日期：2015.11.9

  A mild and convenient synthesis of carbazoles by TfOTMS (trimethylsilyl trifluoromethanesulfonate)‐catalyzed ring‐opening annulation of 2‐amidodihydrofurans is presented with a high degree of chemoselectivity and regioselectivity. This procedure was also scaled up to a gram‐scale synthesis. The reaction could involve an iminonium intermediate through a series of CO, CN bond cleavages, CC bond formations

  TfOTMS（三氟甲磺酸三甲基甲硅烷基酯）催化2-酰胺基二氢呋喃的开环环合反应温和方便，具有高度的化学选择性和区域选择性。该程序也按比例放大至克级合成。该反应可涉及通过一系列的中间Ç一个亚铵 O，C  N键裂解，C  C键的形成，和1,2-迁移过程。
• Alkali-Induced Ring-Opening of 2-Amidodihydrofuran and Manganese-Catalyzed Aerobic Dehydrogenation Annulation: Access to Functionalized Oxazole
  作者：Pan Li、Jingjing Zhao、Xinjian Li、Fuwei Li

  DOI：10.1021/acs.joc.7b00112

  日期：2017.5.5

  functionalized oxazoles from 2-amidodihydrofurans has been achieved by alkali-induced intramolecular C–O bond cleavage and formation using air as a green oxidant. Moreover, these functionalized oxazoles could be readily transformed into the corresponding oxazole-substituted pyrazoles and 2H-azirines.

  通过使用空气作为绿色氧化剂，通过碱诱导的分子内C-O键裂解和形成，已经成功地从2-酰胺基二氢呋喃合成了功能化的恶唑。而且，这些官能化的恶唑可以容易地转化成相应的恶唑取代的吡唑和2 H-叠氮基。