N,4,5,5-tetramethyl-2-oxo-2,5-dihydrofuran-3-carboxamide | 1108179-86-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: N,4,5,5-tetramethyl-2-oxo-2,5-dihydrofuran-3-carboxamide
• 英文别名: 2-imino-3-(N-methyl)carbamoyl-4,5,5-trimethyl-2,5-dihydrofuran；2-imino-N,4,5,5-tetramethylfuran-3-carboxamide
• CAS: 1108179-86-7
• 化学式: C₉H₁₄N₂O₂
• 分子量: 182.222
• InChiKey: CULCCYVBLPJJHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  62.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,4,5,5-tetramethyl-2-oxo-2,5-dihydrofuran-3-carboxamide 在 盐酸 作用下， 以 苯 为溶剂， 以97%的产率得到2-imino-3-(N-methyl)carbamoyl-4,5,5-trimethyl-2,5-dihydrofuran hydrochloride
  参考文献：
  名称：

  The Synthesis of New 2-Iminoderivatives of 2,5-Dihydrofurans and Their Chemical Transformations

  摘要：

  The new 2-iminoderivatives of 2,5-dihydrofurans, their salts, and some products of their transformations have been synthesized by the interaction of accessible tertiary alpha-ketols with amides of cyanoacetic acid. It was showed that the data and the supposed mechanism of the above-mentioned interaction described previously in literature are incorrect and do not correspond to the reality.

  DOI：

  10.1080/00397910701739022
• 作为产物：
  描述：

  3-羟基-3-甲基-2-丁酮 、 2-氰基-N-甲基乙酰胺 反应 5.0h， 以93%的产率得到N,4,5,5-tetramethyl-2-oxo-2,5-dihydrofuran-3-carboxamide
  参考文献：
  名称：

  The Synthesis of New 2-Iminoderivatives of 2,5-Dihydrofurans and Their Chemical Transformations

  摘要：

  The new 2-iminoderivatives of 2,5-dihydrofurans, their salts, and some products of their transformations have been synthesized by the interaction of accessible tertiary alpha-ketols with amides of cyanoacetic acid. It was showed that the data and the supposed mechanism of the above-mentioned interaction described previously in literature are incorrect and do not correspond to the reality.

  DOI：

  10.1080/00397910701739022

文献信息

• Synthesis of new derivatives of 2-imino-2,5-dihydrofurans
  作者：Aida Avetisyan、Lusine Karapetyan

  DOI：10.1515/hc-2012-0113

  日期：2012.12.1

  New N-substituted 2-imino-2,5-dihydrofurans were synthesized by using several efficient approaches starting from readily available 2-imino-2,5-dihydrofurans. All new compounds were characterized by NMR and IR spectral data and elemental analysis.

  通过使用几种高效方法，从易得的2-亚亚胺-2,5-二氢呋喃合成了新的N-取代的2-亚亚胺-2,5-二氢呋喃。所有新化合物均通过核磁共振和红外光谱数据以及元素分析进行了表征。

• Synthesis of New Bis-Iminodihydrofurans
  作者：Gayane G. Tokmajyan、Lusine V. Karapetyan

  DOI：10.5935/0103-5053.20150350

  日期：——

  A new synthetic pathway to new bis-iminodihydrofurans is proposed, which involves the synthesis of N-substituted iminodihydrofurans from reaction of iminodihydrofurans with 2-cyanoacetohydrazide and their condensation with tertiary alpha-hydroxyketones. This sequence of reactions opens the new approach to the synthesis of novel polyheteroconjugated systems consisting from iminodihydrofuran rings. The methodology is simple, rapid and inexpensive affording high yields of the potentially bioactive products.
• Synthesis and Antibacterial Activity of N-Substituted 2-(Benzylimino)-4-styryl-2,5-dihydrofuran-3-carboxamides
  作者：L. V. Karapetyan、G. G. Tokmajyan、H. M. Stepanyan

  DOI：10.1134/s1070428021120113

  日期：2021.12
• Synthesis of 2-imino-4-vinyl-2,5-dihydrofuran-3-carboxamides and some their chemical transformations
  作者：A. A. Avetisyan、L. V. Karapetyan、M. D. Tadevosyan

  DOI：10.1134/s1070428009070082

  日期：2009.7

  2-Imino-2,5-dihydrofuran-3-carboxamides containing 2-phenyl- and 2-furylvinyl substituents in position 4 of the furan ring were synthesized by condensation of 2-imino-4-methyl-2,5-dihydrofuran-3-carboxamides with the corresponding aldehydes. Acid hydrolysis of 4-(2-arylvinyl)-2-imino-2,5-dihydrofuran-3-carboxamides gave 4-(2-arylvinyl)-2-oxo-2,5-dihydrofuran-3-carboxamides, and their condensation with malononitrile resulted in the formation of 2-dicyanomethylidene derivatives.
• Synthesis and hydrolysis of bicyclic 2-imino-2,5-dihydrofurans fused to a pyridine ring
  作者：A. A. Avetisyan、L. V. Karapetyan、M. D. Tadevosyan

  DOI：10.1134/s1070428010080257

  日期：2010.8