4-(2-nitrophenyl)-2,4-dioxobutanoic acid | 446251-68-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(2-nitrophenyl)-2,4-dioxobutanoic acid
• 英文别名: 4-(2-nitro-phenyl)-2,4-dioxo-butyric acid；4-(2-Nitro-phenyl)-2,4-dioxo-buttersaeure
• CAS: 446251-68-9
• 化学式: C₁₀H₇NO₆
• 分子量: 237.169
• InChiKey: WDBWRLGZZSEBID-UHFFFAOYSA-N

物化性质

• 熔点：
  167 °C (decomp)
• 沸点：
  454.6±25.0 °C(Predicted)
• 密度：
  1.505±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(2-nitrophenyl)-2,4-dioxobutanoic acid 在 ammonium hydroxide 、 钯 作用下， 生成 犬尿喹酸
  参考文献：
  名称：

  Musajo et al., Gazzetta Chimica Italiana, 1950, vol. 80, p. 161,169

  摘要：

  DOI：
• 作为产物：
  描述：

  邻硝基苯乙酮 在 盐酸 、 sodium ethanolate 作用下， 生成 4-(2-nitrophenyl)-2,4-dioxobutanoic acid
  参考文献：
  名称：

  Musajo et al., Gazzetta Chimica Italiana, 1950, vol. 80, p. 161,169

  摘要：

  DOI：

文献信息

• Makino et al., Kumamoto Medical Journal, 1954, vol. 6, p. 122,124
  作者：Makino et al.

  DOI：——

  日期：——
• “Untypical Aging Off-Flavor” in Wine:  Synthesis of Potential Degradation Compounds of Indole-3-acetic Acid and Kynurenine and Their Evaluation as Precursors of 2-Aminoacetophenone
  作者：Katrin Hoenicke、Ole Borchert、Kai Grüning、Thomas J. Simat

  DOI：10.1021/jf011672r

  日期：2002.7.1

  Kynurenine (1) and indole-3-acetic acid (2) are considered as potential precursors of 2-amino-acetophenone (3), which is regarded to be the aroma impact compound causing an "untypical aging off-flavor" (UTA) in Vitis vinifera wines. The mechanism of the formation of 3 was studied using model fermentation and model sulfuration media spiked with 1 or 2 as potential precursors. Possible degradation products such as kynurenamine (4) and kynurenic acid (5), or skatole (6), 2-oxoskatole (7), 2-formamidoacetophenone (8), 2-oxindole-3-acetic acid (9), and 3-(2-formylaminophenyl)-3-oxopropionic acid (10) were evaluated by HPLC-UV of the fermentation and sulfuration media and comparison with synthesized 7, 8, 9, and 10. The synthesis of the possible precursor 4-(2-aminophenyl)-2,4-dioxobutanoic acid (111), a proposed metabolite of 1 failed because a spontaneous cyclization yields 5 and N-oxo-kynurenic acid (12), but not 11. It could be shown that the formation of 3 is triggered by an oxidative degradation of 2 after sulfuration with potassium bisulfite via the intermediates 10 and 8. However, no formation of 3 occurred during sulfuration of a model wine spiked with 1 or during fermentation of a model must spiked with 1 or 2.
• Makino et al., Kumamoto Medical Journal, 1953, vol. 6, p. 122,127
  作者：Makino et al.

  DOI：——

  日期：——