3-methyl-5-phenyl-Δ⁴-oxazolin-2-ylidenmalononitril | 145162-39-6

• 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: 3-methyl-5-phenyl-Δ⁴-oxazolin-2-ylidenmalononitril
• 英文别名: 2-(3-Methyl-5-phenyl-1,3-oxazol-2-ylidene)propanedinitrile
• CAS: 145162-39-6
• 化学式: C₁₃H₉N₃O
• 分子量: 223.234
• InChiKey: KPNVZKOWBCRZPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  60
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  哌啶 、 3-methyl-5-phenyl-Δ⁴-oxazolin-2-ylidenmalononitril 反应 1.0h， 以65%的产率得到4-amino-5-benzoyl-1-methyl-2-piperidin-1-yl-pyrrole-3-carbonitrile
  参考文献：
  名称：

  New syntheses of 2,4-diaminopyrroles and aminopyrrolinones

  摘要：

  Oxazolin-2-ylidene-malononitriles 3a-d, obtainable from thioketenaminals and alpha-halogen-ketones, react with primary and secondary amines to afford 2,4-diamino-pyrroles 5a-h. Mercaptobenzen as nucleophilic agent gives the 4-amino-2-phenylthio-pyrrole 5j. Analogously, cyano-(3,5-diphenyl-3H-oxazol-2-ylidene)-acetic acid methyl esters were prepared as intermediates for the synthesis of 2-amino-4-oxo-pyrrolines 10a-d. The isomeric 4-amino-2-oxo-pyrrolines 13a-d can be obtained from 4-amino-2-methoxy-pyrroles, which serves as proof for the position of substituents. The structures were investigated by H-1 and C-13 NMR spectroscopy.

  DOI：

  10.1007/bf00807103
• 作为产物：
  描述：

  [(methylthio)(methylamino)methylene]malononitrile 、 2-溴苯乙酮 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.2h， 以50%的产率得到3-methyl-5-phenyl-Δ⁴-oxazolin-2-ylidenmalononitril
  参考文献：
  名称：

  Zur Synthese von 3-Amino-pyrrolen durch Thorpe-Ziegler-Cyclisierung

  摘要：

  N-Aryl and alkylaminomethylene cyanacetic acid derivatives 1 react with alpha-halogencarbonyl compounds 2 in the presence of potassium carbonate/sodium ethoxide to yield the substituted 3-amino-pyrroles 6. Using the same principle of cyclization pyrrole derivatives 6 can also be obtained by reaction of beta-chloro- and beta-alkoxymethylenemalononitriles 4 with beta-aminocarbonyl compounds 5. From the malononitrile derivatives 1 containing the methylthio group in the beta-position, and alpha-halogen ketones 7, the 2-dicyanomethylene oxazolines 8 arise which undergo alkoholysis by treatment with sodium alkoxide to form the 3-amino-5-alkoxy-pyrrole derivatives 9.

  DOI：

  10.1002/prac.19923340608