4-羟基-5-硝基-2-糠醛 | 113849-14-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 中文名称: 4-羟基-5-硝基-2-糠醛
• 英文名称: 4-hydroxy-5-nitro-furan-2-carbaldehyde
• 英文别名: 4-Hydroxy-5-nitrofuran-2-carbaldehyde
• CAS: 113849-14-2
• 化学式: C₅H₃NO₅
• mdl: MFCD18813975
• 分子量: 157.083
• InChiKey: MSCCTOKBJZRLSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  96.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-氨基噁唑烷-2-酮 、 4-羟基-5-硝基-2-糠醛 在 盐酸 作用下， 生成 3-(5-nitro-4-hydroxy-furan-2-ylmethyleneamino)-oxazolidin-2-one
  参考文献：
  名称：

  Metabolic and photochemical hydroxylation of 5-nitro-2-furancarboxaldehyde derivatives

  摘要：

  The potassium salt of 1-[[(5-aco-nitro-4,5-dihydro-4-oxo-2-furanyl)methylene]amino]-2,4-imidazolidinedione (4) was isolated from the urine of rats fed nitrofurantoin. An aldehyde absorbing at 400 nm was synthesized photochemically, in less than 1% yield, from 5-nitro-2-furancarboxaldehyde diacetate (1), and the hydroxylamine (2), 3-amino-2-oxazolidinone (3a-c), and 1-amino-2,4-imidazolidinedione (4) derivatives were prepared. On the basis of ir and NMR data 2, 3b,c, and 4 are considered derivatives of 4-hydroxy-5-nitro-2-furancarboxaldehyde which are mainly in the aci-nitro form. Methyl and ethyl nitronic esters of 3b were synthesized. The photochemical hydroxylation of 1 also yields 3,4-dihydroxy-5-nitro-2-furancarboxaldehyde, isolated as 3-[[(3,4-dimethoxy-5-nitro-2-furanyl)-methylene[amino[-2-oxazolidinone (7).

  DOI：

  10.1021/jm00227a032

文献信息

• Metabolic and photochemical hydroxylation of 5-nitro-2-furancarboxaldehyde derivatives
  作者：Joanne Olivard、Gordon M. Rose、George M. Klein、James P. Heotis

  DOI：10.1021/jm00227a032

  日期：1976.5

  The potassium salt of 1-[[(5-aco-nitro-4,5-dihydro-4-oxo-2-furanyl)methylene]amino]-2,4-imidazolidinedione (4) was isolated from the urine of rats fed nitrofurantoin. An aldehyde absorbing at 400 nm was synthesized photochemically, in less than 1% yield, from 5-nitro-2-furancarboxaldehyde diacetate (1), and the hydroxylamine (2), 3-amino-2-oxazolidinone (3a-c), and 1-amino-2,4-imidazolidinedione (4) derivatives were prepared. On the basis of ir and NMR data 2, 3b,c, and 4 are considered derivatives of 4-hydroxy-5-nitro-2-furancarboxaldehyde which are mainly in the aci-nitro form. Methyl and ethyl nitronic esters of 3b were synthesized. The photochemical hydroxylation of 1 also yields 3,4-dihydroxy-5-nitro-2-furancarboxaldehyde, isolated as 3-[[(3,4-dimethoxy-5-nitro-2-furanyl)-methylene[amino[-2-oxazolidinone (7).