4-氨基-5-(4-溴苯甲酰基)-N-苯基-1,2-恶唑-3-甲酰胺 | 830326-87-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-氨基-5-(4-溴苯甲酰基)-N-苯基-1,2-恶唑-3-甲酰胺
• 英文名称: 4-amino-5-(4-bromobenzoyl)-N-phenylisoxazole-3-carboxamide
• 英文别名: 3-Isoxazolecarboxamide, 4-amino-5-(4-bromobenzoyl)-N-phenyl-；4-amino-5-(4-bromobenzoyl)-N-phenyl-1,2-oxazole-3-carboxamide
• CAS: 830326-87-9
• 化学式: C₁₇H₁₂BrN₃O₃
• 分子量: 386.205
• InChiKey: JQBJJDRRYAORQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 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：

  2-氰基乙酰苯胺 在 lithium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 32.0h， 生成 4-氨基-5-(4-溴苯甲酰基)-N-苯基-1,2-恶唑-3-甲酰胺
  参考文献：
  名称：

  Synthesis of 4-aminoisoxazole-3-carboxamides using base-promoted nitrosation of N-substituted cyanoacetamides

  摘要：

  The reactions of N-substituted cyanoacetamides with EtONO in the presence of an equimolar amount of EtONa afforded the corresponding sodium salts of hydroxyiniino derivatives in 70-95% yields. The latter were transformed into 4-amino-5-(4-bromobenzoyl)isoxazole-3-carboxamides in 30-57% yields using the known method.

  DOI：

  10.1023/b:rucb.0000035646.13790.8a

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。
• Theoretical study of the mechanism of formation of 4-aminoisoxazoles. 2*. An unusual rearrangement of oximinonitriles
  作者：V. P. Kislyi、E. B. Danilova、V. N. Solkan

  DOI：10.1007/s10593-013-1342-x

  日期：2013.10

  4-aminoisoxazoles and 5-aminooxazoles are formed from the anion of one of the oximinonitrile lithium complexes. The formation of 5-aminooxazoles proceeds through an unusual anion rearrangement. The thermodynamic parameters of the transition states were calculated to explain the predominant formation of 4-aminoisoxazoles.

  在锂离子的存在下，肟基腈的碱催化环化反应会生成4-氨基异恶唑，有时还会生成5-氨基恶唑。使用密度泛函理论以及HF和MP2方法进行建模表明，4-氨基异恶唑和5-氨基恶唑均由一种肟基腈锂配合物的阴离子形成。5-氨基恶唑的形成通过不寻常的阴离子重排进行。计算了过渡态的热力学参数以解释4-氨基异恶唑的主要形成。
• 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。
• Synthesis of 4-aminoisoxazole-3-carboxamides using base-promoted nitrosation of N-substituted cyanoacetamides
  作者：V. P. Kislyi、E. B. Danilova、E. P. Zakharov、V. V. Semenov

  DOI：10.1023/b:rucb.0000035646.13790.8a

  日期：2004.3

  The reactions of N-substituted cyanoacetamides with EtONO in the presence of an equimolar amount of EtONa afforded the corresponding sodium salts of hydroxyiniino derivatives in 70-95% yields. The latter were transformed into 4-amino-5-(4-bromobenzoyl)isoxazole-3-carboxamides in 30-57% yields using the known method.