N-benzyl-(4,5,5-trimethyl-2,5-dihydro-2-oxofuran)-3-carboxamide | 34494-95-6

• 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-benzyl-(4,5,5-trimethyl-2,5-dihydro-2-oxofuran)-3-carboxamide
• 英文别名: 3-(N-benzyl)carbamoyl-4,5,5-trimethyl-2,5-dihydrofuran-2one；N-benzyl-2,5-dihydro-4,5,5-trimethyl-2-oxofuran-3-carboxamide；4,5,5-trimethyl-2-oxo-2,5-dihydro-furan-3-carboxylic acid benzylamide；N-benzyl-4,5,5-trimethyl-2-oxofuran-3-carboxamide
• CAS: 34494-95-6
• 化学式: C₁₅H₁₇NO₃
• 分子量: 259.305
• InChiKey: JGJBNYRTKHBWGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氰基-N-(苯基甲基)-乙酰胺 在 盐酸 、 水 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 11.0h， 生成 N-benzyl-(4,5,5-trimethyl-2,5-dihydro-2-oxofuran)-3-carboxamide
  参考文献：
  名称：

  通过后续反应有效合成新丁烯内酯：用于合成原始亚氨基内酯，双亚氨基内酯和双内酯的应用

  摘要：

  根据α-羟基酮的两种策略，我们通过随后的酯化-缩合或加成-缩合反应，开发了二十四种新的亚氨基内酯，双亚氨基内酯和双内酯。描述了双亚氨基内酯的X射线衍射数据，并给出了令人感兴趣的螺旋柱填料。

  DOI：

  10.1016/j.tet.2010.12.062

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。
• The Synthesis of New 2-Iminoderivatives of 2,5-Dihydrofurans and Their Chemical Transformations
  作者：Aida Avetissyan、Lousine Karapetyan

  DOI：10.1080/00397910701739022

  日期：2008.12.16

  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.
• Efficient synthesis of new butenolides by subsequent reactions: application for the synthesis of original iminolactones, bis-iminolactones and bis-lactones
  作者：Nawel Cheikh、Nathalie Bar、Nourredine Choukchou-Braham、Bachir Mostefa-Kara、Jean-François Lohier、Jana Sopkova、Didier Villemin

  DOI：10.1016/j.tet.2010.12.062

  日期：2011.2

  We have developed the synthesis of twenty four new iminolactones, bis-iminolactones and bis-lactones by subsequent esterification–condensation or addition–condensation reactions according to two strategies from α-hydroxyketones. The X-ray diffraction data of a bis-iminolactone is described and present an interesting helical column packing.

  根据α-羟基酮的两种策略，我们通过随后的酯化-缩合或加成-缩合反应，开发了二十四种新的亚氨基内酯，双亚氨基内酯和双内酯。描述了双亚氨基内酯的X射线衍射数据，并给出了令人感兴趣的螺旋柱填料。