4-acetyl-3-amino-5-oxo-3-hexenenitrile | 106823-51-2

• 分子结构分类: 有机化合物
• 英文名称: 4-acetyl-3-amino-5-oxo-3-hexenenitrile
• 英文别名: 4-acetyl-3-amino-5-oxohex-3-enenitrile
• CAS: 106823-51-2
• 化学式: C₈H₁₀N₂O₂
• 分子量: 166.18
• InChiKey: DELYCBSGQBPSET-UHFFFAOYSA-N

物化性质

• 沸点：
  386.3±42.0 °C(Predicted)
• 密度：
  1.145±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.29
• 重原子数：
  12.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  83.95
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-acetyl-3-amino-5-oxo-3-hexenenitrile 在 肼 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以55%的产率得到(E)-3-Amino-3-(3,5-dimethyl-1H-pyrazol-4-yl)-acrylonitrile
  参考文献：
  名称：

  Reaction of β-Cyanomethylene-β-enamino Diketones and -keto Esters with Hydrazines: Synthesis of Pyrazole and Pyridine Derivatives

  摘要：

  DOI：

  10.3987/com-98-s(h)73
• 作为产物：
  描述：

  (2Z,4Z)-4-Acetyl-3-amino-5-hydroxy-hexa-2,4-dienenitrile 以 氘代氯仿 为溶剂， 生成 4-acetyl-3-amino-5-oxo-3-hexenenitrile
  参考文献：
  名称：

  Various approaches to the use of 3-acetyl-2-amino-4-hydroxy-1,3-pentadienecarbonitrile in heterocyclic synthesis

  摘要：

  Two approaches to the use of 3-acetyl-2-amino-4-hydroxy-1,3-pentadienecarbonitrile (1) in heterocyclic synthesis are considered. A method for preparing 3-acetyl-4-amino-5-cyano-2-methylpyridine directly from 1 and N,N-dimethylformamide dimethylacetal (DMF DMA) was proposed, together with a synthetic route to 2-(2-amino-3-cyano-6-hydroxyphenyl)-8-cyano-5-hydroxy-4-methylquinoline based an the transformation of hydroxyvinyl ketone 1 into its diphenylboron chelate and condensation of the latter with DMF DMA.

  DOI：

  10.1007/bf02495360

文献信息

• Metal-catalysed carbon-carbon bond formation in the reaction of malononitrile with β-dicarbonyls
  作者：Augusto C. Veronese、Carlo F. Morelli、Rosella Callegari、Marino Basato

  DOI：10.1016/s1381-1169(97)00077-0

  日期：1997.10

  Nickel acetylacetonate effectively catalyses the carbon-carbon bond formation between malononitrile and beta-dicarbonyls. In these metal-catalysed reactions malononitrile behaves as an electrophile towards the intercarbonylic carbon, so exhibiting a reverse reactivity compared with that one under basic or thermal conditions. The resulting organic products are beta-cyanomethylene-beta-enamino dicarbonyls (2a-h), which are obtained in good-to fair yield. beta-Iminodicarbonyl complexes of nickel(II) and copper(II), which are likely intermediates in the catalytic cycle, are synthesised by reaction of the metal beta-carbonylenolate with malononitrile or of the metal acetate with the catalysis product (2a, d).