4-(4-nitrophenyl)-3-oxobutanenitrile | 206346-34-1

• 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: 4-(4-nitrophenyl)-3-oxobutanenitrile
• 英文别名: 4-Nitro-I(2)-oxobenzenebutanenitrile
• CAS: 206346-34-1
• 化学式: C₁₀H₈N₂O₃
• 分子量: 204.185
• InChiKey: QXCVDDSARGZFFA-UHFFFAOYSA-N

物化性质

• 沸点：
  371.5±22.0 °C(Predicted)
• 密度：
  1.295±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  86.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(4-nitrophenyl)-3-oxobutanenitrile 在 吡啶 、 盐酸 、 吡啶盐酸盐 、 铁粉 、 氯化铵 、 lithium chloride 、 三氯氧磷 作用下， 以 乙二醇二甲醚 、 乙醇 、 水 、 甲苯 为溶剂， 反应 21.0h， 生成 N-(4-(4-((3-chloro-4-fluorophenyl)amino)-5-cyanopyridin-3-yl)phenyl)-4-((4-methylpiperazin-1-yl)methyl)benzamide
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel pyrimidine, 3-cyanopyridine and m-amino-N-phenylbenzamide based monocyclic EGFR tyrosine kinase inhibitors

  摘要：

  36 new compounds with the typical skeleton of 4-anilino-5-vinyl/ethynyl pyrimidine, 4-anilino-3-cyano-5-vinyl/ethynyl/phenyl pyridine, and m-amino-N-phenylbenzamide, are designed, synthesized and selectively tested on EGFR, ErbB-2 kinases, and A-549, HL60 cells growth inhibition. Results from the bioactivity and chemical structures yield preliminary structure-activity relationships (SARs). The most potent 5-ethynylpyrimidine derivative 20a has an IC50 value of 45 nM to EGFR kinase. Several compounds of other series also show IC50 values <1 mu M for EGFR and <5 mu M for A-549 and HL60 cells growth inhibition. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2013.03.053
• 作为产物：
  描述：

  ethyl 2-cyano-4-(4-nitrophenyl)-3-oxobutanoate 在 水 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 以81%的产率得到4-(4-nitrophenyl)-3-oxobutanenitrile
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel pyrimidine, 3-cyanopyridine and m-amino-N-phenylbenzamide based monocyclic EGFR tyrosine kinase inhibitors

  摘要：

  36 new compounds with the typical skeleton of 4-anilino-5-vinyl/ethynyl pyrimidine, 4-anilino-3-cyano-5-vinyl/ethynyl/phenyl pyridine, and m-amino-N-phenylbenzamide, are designed, synthesized and selectively tested on EGFR, ErbB-2 kinases, and A-549, HL60 cells growth inhibition. Results from the bioactivity and chemical structures yield preliminary structure-activity relationships (SARs). The most potent 5-ethynylpyrimidine derivative 20a has an IC50 value of 45 nM to EGFR kinase. Several compounds of other series also show IC50 values <1 mu M for EGFR and <5 mu M for A-549 and HL60 cells growth inhibition. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2013.03.053

文献信息

• Solid-phase C-acylation of active methylene compounds
  作者：Mui Mui Sim、Cheng Leng Lee、A. Ganesan

  DOI：10.1016/s0040-4039(98)00173-7

  日期：1998.4

  Active methylene compounds were attached to the Wang resin by an ester linkage. C-acylation was achieved with a reactive species generated in situ by the combination of a carboxylic acid, diethyl phosphorocyanidate, and triethylamine. Cleavage from the resin with simultaneous decarboxylation gave the products in moderate to good yield. (C) 1998 Elsevier Science Ltd. All rights reserved.