ethyl 4-acetyl-5-amino-2-methylfuran-3-carboxylate | 67271-62-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: ethyl 4-acetyl-5-amino-2-methylfuran-3-carboxylate
• 英文别名: 4-acetyl-5-amino-2-methyl-furan-3-carboxylic acid ethyl ester；Ethyl 4-acetyl-5-amino-2-methyl-3-furoate
• CAS: 67271-62-9
• 化学式: C₁₀H₁₃NO₄
• 分子量: 211.218
• InChiKey: FNNUOEITECDFHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  82.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 4-acetyl-5-amino-2-methylfuran-3-carboxylate 在 potassium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 以54%的产率得到2-acetyl-4-oxopentanenitrile
  参考文献：
  名称：

  N-Heterocyclic Carbene-Catalyzed Annulation of α-Cyano-1,4-diketones with Ynals

  摘要：

  In this paper, the first stereoselective annulation reaction between alpha-cyano-1,4-diketones and ynals, mediated by catalytic amounts of a triazolium salt precatalyst and cocatalytic amounts of a weak carboxylate base, is disclosed. The title transformation proceeds smoothly under mild reaction conditions and generates three contiguous stereogenic centers, one of which is a quaternary acetal carbon. This reaction tolerates a wide variety of electronically distinct substituents on both reaction partners and affords privileged bicyclic scaffolds in 61-90% isolated yields and with up to 20:1 diastereomeric preference.

  DOI：

  10.1021/ol3022287
• 作为产物：
  描述：

  (1-氰基-2-氧代丙基)钠 、 2-氯乙酰乙酸乙酯 以 水 为溶剂， 反应 1.5h， 以77%的产率得到ethyl 4-acetyl-5-amino-2-methylfuran-3-carboxylate
  参考文献：
  名称：

  N-Heterocyclic Carbene-Catalyzed Annulation of α-Cyano-1,4-diketones with Ynals

  摘要：

  In this paper, the first stereoselective annulation reaction between alpha-cyano-1,4-diketones and ynals, mediated by catalytic amounts of a triazolium salt precatalyst and cocatalytic amounts of a weak carboxylate base, is disclosed. The title transformation proceeds smoothly under mild reaction conditions and generates three contiguous stereogenic centers, one of which is a quaternary acetal carbon. This reaction tolerates a wide variety of electronically distinct substituents on both reaction partners and affords privileged bicyclic scaffolds in 61-90% isolated yields and with up to 20:1 diastereomeric preference.

  DOI：

  10.1021/ol3022287

文献信息

• Synthesis of some 2-aminofurans from cyanoacetone enolate and their rearrangement to 3-cyanopyrroles with ammonia
  作者：John F. Blount、David L. Coffen、David A. Katonak

  DOI：10.1021/jo00414a006

  日期：1978.9
• BLOUNT J. F.; COFFEN D. L.; KATONAK D. A., J. ORG. CHEM., 1978, 43, NO 20, 3821-3824
  作者：BLOUNT J. F.、 COFFEN D. L.、 KATONAK D. A.

  DOI：——

  日期：——