N-phenyl-4-amino-5-benzoylisoxazole-3-carboxamide

• 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-amino-5-benzoylisoxazole-3-carboxamide
• 英文别名: 4-amino-5-benzoyl-N-phenylisoxazole-3-carboxamide；3-Isoxazolecarboxamide, 4-amino-5-benzoyl-N-phenyl-；4-amino-5-benzoyl-N-phenyl-1,2-oxazole-3-carboxamide
• 化学式: C₁₇H₁₃N₃O₃
• mdl: MFCD06619361
• 分子量: 307.309
• InChiKey: WPYUBXBPVRNYSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  98.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-hydroxy-2-oxo-2-(phenylamino)acetimidoyl cyanide 在 lithium perchlorate trihydrate 、 potassium hydrogencarbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.58h， 生成 N-phenyl-4-amino-5-benzoylisoxazole-3-carboxamide
  参考文献：
  名称：

  Theoretical study of the mechanism of formation of 4-aminoisoxazoles. 1. Structure of 2-cyano-2-[(2-oxo-2-phenylethoxy)imino]-N-phenylacetamide in the crystal and solution

  摘要：

  In a study of the mechanism for formation of 4-aminoisoxazoles, we carried out a conformational analysis of substituted oximinonitriles using DFT, HF, and MP2 methods. The structure of 2-cyano-2-[(2-oxo-2-phenylethoxy)imino]-N-phenylacetamide in the crystal is in good agreement with the conformation in solution determined using the B3LYP/6-311++G(d,p) density functional method.

  DOI：

  10.1007/s10593-013-1341-y

文献信息

• Synthesis of 3,5-disubstituted 4-aminoisoxazoles by cyclization of O-(β-oxoalkyl)-substituted α-hydroxyimino nitriles
  作者：V. P. Kislyi、E. B. Danilova、V. V. Semenov

  DOI：10.1007/s11172-005-0379-0

  日期：2005.5

  4-Amino-5-benzoyl(acetyl)isoxazole-3-carboxamides were prepared by cyclization of α-hydroxyimino nitriles O-alkylated with bromoacetophenones (bromoacetone). The purity of the target 4-aminoisoxazoles can be substantially increased by treating O-alkylated oximes with LiClO4 before cyclization.

  4- 氨基-5-苯甲酰基（乙酰基）异噁唑-3-甲酰胺是通过α-羟基亚氨基腈 O-烷基化溴代苯乙酮（溴丙酮）环化制备的。在环化之前用 LiClO4 处理 O-烷基化肟，可以大大提高目标 4-氨基异噁唑的纯度。
• Competitive formation of 4-aminoisoxazoles and 5-aminooxazoles in the cyclization reactions of O-alkylated hydroxyimino nitriles
  作者：V. P. Kislyi、E. B. Danilova、V. V. Semenov、A. A. Yakovenko、F. M. Dolgushin

  DOI：10.1007/s11172-006-0495-5

  日期：2006.10

  Base-catalyzed cyclization of O-alkylated α-hydroxyimino nitriles gave mixtures of 4-aminoisoxazoles and 5-aminooxazoles, their ratio depending on the substituent structures and the reaction conditions. The formation mechanism of 5-aminooxazoles in this reaction is discussed.

  O-烷基化α-羟基亚氨基腈的碱催化环化得到4-氨基异恶唑和5-氨基恶唑的混合物，它们的比例取决于取代基结构和反应条件。讨论了该反应中5-氨基恶唑的形成机理。