ethyl 4-((4-cyanophenyl)(methyl)amino)-3-oxobutanoate | 1364822-83-2

• 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: ethyl 4-((4-cyanophenyl)(methyl)amino)-3-oxobutanoate
• 英文别名: ethyl 4-(4-cyano-N-methylanilino)-3-oxobutanoate
• CAS: 1364822-83-2
• 化学式: C₁₄H₁₆N₂O₃
• mdl: MFCD19026567
• 分子量: 260.293
• InChiKey: IVTKWSFJPZWNBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.357
• 拓扑面积：
  70.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 4-((4-cyanophenyl)(methyl)amino)-3-oxobutanoate 在 肼 作用下， 以 乙醇 为溶剂， 生成 4-(Methyl((5-oxo-2,5-dihydro-1H-pyrazol-3-yl)methyl)amino)benzonitrile
  参考文献：
  名称：

  Arylazanylpyrazolone Derivatives as Inhibitors of Mutant Superoxide Dismutase 1 Dependent Protein Aggregation for the Treatment of Amyotrophic Lateral Sclerosis

  摘要：

  The arylsulfanylpyrazolone and aryloxanylpyrazolone scaffolds previously were reported to inhibit Cu/Zn superoxide dismutase 1 dependent protein aggregation and to extend survival in the ALS mouse model. However, further evaluation of these compounds indicated weak pharmacokinetic properties and a relatively low maximum tolerated dose. On the basis of an ADME analysis, a new series of compounds, the arylazanylpyrazolones, has been synthesized, and structure-activity relationships were determined. The SAR results showed that the pyrazolone ring is critical to cellular protection. The NMR, IR, and computational analyses suggest that phenol-type tautomers of the pyrazolone ring are the active pharmacophore with the arylazanylpyrazolone analogues. A comparison of experimental and calculated IR spectra is shown to be a valuable method to identify the predominant tautomer.

  DOI：

  10.1021/jm400079a
• 作为产物：
  描述：

  4-氯乙酰乙酸乙酯 、 N-甲基-4-氰基苯胺 在 碳酸氢钠 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以58%的产率得到ethyl 4-((4-cyanophenyl)(methyl)amino)-3-oxobutanoate
  参考文献：
  名称：

  Direct Amination of γ-Halo-β-ketoesters with Anilines

  摘要：

  The direct amination of alpha-haloacetoacetates with anilines is described. Compared to existing methods, this simple protocol provides an attractive strategy to prepare diverse gamma-anilino-beta-ketoesters in one step. Good to excellent yields of the amination products were obtained under robust conditions, providing versatile and useful scaffolds.

  DOI：

  10.1021/jo300239e