N-phenyl-(4,5,5-trimethyl-2,5-dihydro-2-oxofuran)-3-carboxamide | 34494-90-1

• 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: N-phenyl-(4,5,5-trimethyl-2,5-dihydro-2-oxofuran)-3-carboxamide
• 英文别名: 2,5-dihydro-4,5,5-trimethyl-2-oxo-N-phenylfuran-3-carboxamide；4,5,5-trimethyl-2-oxo-N-phenylfuran-3-carboxamide
• CAS: 34494-90-1
• 化学式: C₁₄H₁₅NO₃
• 分子量: 245.278
• InChiKey: ZMZOQQMQVNXNNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-phenyl-(4,5,5-trimethyl-2,5-dihydro-2-oxofuran)-3-carboxamide 在 硫酸 、 水 作用下， 反应 3.0h， 以80%的产率得到4,5,5-trimethyl-2-oxofuran-3-carboxylic acid
  参考文献：
  名称：

  Synthesis of novel N-aryl-2,5-dihydro-2-iminofuran-3-carboxamides and their chemical transformations

  摘要：

  Novel N-aryl-2,5-dihydro-2-iminofuran-3-carboxamides have been synthesized by condensation of tertiary alpha-hydroxyketones with N-aryl-2-cyanoacetamides. The obtained products were transformed to corresponding iminium chlorides, hydrogen sulfates, 2-oxo and 2-(dicyanomethylene) derivatives. All new compounds were characterized by NMR and IR spectral data and elemental analysis.

  DOI：

  10.1007/s00706-011-0615-2
• 作为产物：
  描述：

  3-羟基-3-甲基-2-丁酮 在 盐酸 、 水 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 8.0h， 生成 N-phenyl-(4,5,5-trimethyl-2,5-dihydro-2-oxofuran)-3-carboxamide
  参考文献：
  名称：

  Synthesis of novel N-aryl-2,5-dihydro-2-iminofuran-3-carboxamides and their chemical transformations

  摘要：

  Novel N-aryl-2,5-dihydro-2-iminofuran-3-carboxamides have been synthesized by condensation of tertiary alpha-hydroxyketones with N-aryl-2-cyanoacetamides. The obtained products were transformed to corresponding iminium chlorides, hydrogen sulfates, 2-oxo and 2-(dicyanomethylene) derivatives. All new compounds were characterized by NMR and IR spectral data and elemental analysis.

  DOI：

  10.1007/s00706-011-0615-2

文献信息

• One-pot two-step synthesis of 2,5-dihydro-2-oxofuran-3-carboxamides
  作者：Gayane Tokmajyan、Lusine Karapetyan

  DOI：10.1515/hc-2014-0023

  日期：2014.4.1

  2,5-Dihydro-2-oxofuran-3-carboxamides were synthesized by a one-pot two-step reaction catalyzed by sodium methoxide. Readily available tertiary α-hydroxyketones were condensed with substituted cyanoacetamides to give 2-imino-2,5-dihydrofuran-3-carboxamides that, without isolation, were hydrolized to the title products.

  2,5-二氢-2-氧基呋喃-3-羧酰胺通过一锅两步反应合成，该反应由甲氧基钠催化。易得的三级α-羟基酮与取代的氰基乙酰胺缩合，得到2-亚氨基-2,5-二氢呋喃-3-羧酰胺，而无需分离，即可水解为所述产物。