methyl 3-(4-cyano-2-nitrophenyl)propanoate | 1493774-31-4

• 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: methyl 3-(4-cyano-2-nitrophenyl)propanoate
• CAS: 1493774-31-4
• 化学式: C₁₁H₁₀N₂O₄
• 分子量: 234.211
• InChiKey: KNJHPQNXFXNJPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  95.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3-(4-cyano-2-nitrophenyl)propanoate 在 3,5-二乙酰基-1,4-二氢-2,6-二甲基吡啶 、 camphor-10-sulfonic acid 、 [bis(2,2′‐bipyridine)ruthenium(II)](chloride)₂ hexahydrate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 7-cyano-1-hydroxy-2-oxo-1,2,3,4-tetrahydroquinolin
  参考文献：
  名称：

  Reductive Cyclizations of Nitroarenes to Hydroxamic Acids by Visible Light Photoredox Catalysis

  摘要：

  We have developed a photocatalytic reduction of nitroarenes as an efficient, chemoselective route to biologically important N-phenyl hydroxamic acid scaffolds. Optimal conditions call for 2.5 mol% of a ruthenium photocatalyst, visible light irradiation, and a dihydropyridine terminal reductant. Because of the mild nature of the visible light activation, functional groups that might be sensitive to other non-photochemical reduction methods are easily tolerated.

  DOI：

  10.1055/s-0033-1338419
• 作为产物：
  描述：

  methyl 3-(4-cyano-2-nitrophenyl)acrylate 在 Wilkinson's catalyst 、 氢气 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 反应 72.0h， 以53%的产率得到methyl 3-(4-cyano-2-nitrophenyl)propanoate
  参考文献：
  名称：

  Reductive Cyclizations of Nitroarenes to Hydroxamic Acids by Visible Light Photoredox Catalysis

  摘要：

  We have developed a photocatalytic reduction of nitroarenes as an efficient, chemoselective route to biologically important N-phenyl hydroxamic acid scaffolds. Optimal conditions call for 2.5 mol% of a ruthenium photocatalyst, visible light irradiation, and a dihydropyridine terminal reductant. Because of the mild nature of the visible light activation, functional groups that might be sensitive to other non-photochemical reduction methods are easily tolerated.

  DOI：

  10.1055/s-0033-1338419