2-methyl-3-oxobutyraldehyde sodium salt

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methyl-3-oxobutyraldehyde sodium salt
• 英文别名: Sodium;2-methyl-3-oxobutanal
• 化学式: C₅H₈O₂*Na
• 分子量: 123.107
• InChiKey: ABDFLHHYRXIHNI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.59
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methyl-3-oxobutyraldehyde sodium salt 在 吡啶 、 sodium hydroxide 、 双氧水 、 sodium acetate 、 溶剂黄146 、 锌 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 5.42h， 生成 3,4-dimethyl-3-pyrrolin-2-one
  参考文献：
  名称：

  Synthesis and unusual properties of C-(10)-gem-dimethyl bilirubin analogs

  摘要：

  The characteristic thermodynamically-favored intramolecularly hydrogen-bonded conformation adopted by bilirubin pigments is destabilized by substituting methyl groups on the C(10) central methylene. These methyl groups impose conformation-destabilizing methyl-methylene non-bonded steric interactions with the propionic acid beta-CH2 groups at C(8) and C(12) when the propionic acids are engaged in intramolecular hydrogen bonding with the opposing dipyrrinones. Amphiphilic 10,10-dimethylbilirubins (1) and (2) are found to be more polar, but also more soluble than the parents (3) and (4) in organic solvents; yet, H-1-NMR studies in non-polar solvents indicate that a deformed but folded, intramolecularly hydrogen-bonded conformation is retained. The dimethyl esters of 10,10-dimethylbilirubins 1 and 2 did not exhibit the typical strong tendency of bilirubin dimethyl esters to form intermolecular hydrogen bonds in non-polar solvents such as chloroform and benzene.

  DOI：

  10.1016/s0040-4020(01)80362-8
• 作为产物：
  描述：

  丁酮 、 甲酸乙酯 在 sodium 作用下， 以 乙醚 为溶剂， 反应 14.0h， 生成 2-methyl-3-oxobutyraldehyde sodium salt
  参考文献：
  名称：

  Synthesis and unusual properties of C-(10)-gem-dimethyl bilirubin analogs

  摘要：

  The characteristic thermodynamically-favored intramolecularly hydrogen-bonded conformation adopted by bilirubin pigments is destabilized by substituting methyl groups on the C(10) central methylene. These methyl groups impose conformation-destabilizing methyl-methylene non-bonded steric interactions with the propionic acid beta-CH2 groups at C(8) and C(12) when the propionic acids are engaged in intramolecular hydrogen bonding with the opposing dipyrrinones. Amphiphilic 10,10-dimethylbilirubins (1) and (2) are found to be more polar, but also more soluble than the parents (3) and (4) in organic solvents; yet, H-1-NMR studies in non-polar solvents indicate that a deformed but folded, intramolecularly hydrogen-bonded conformation is retained. The dimethyl esters of 10,10-dimethylbilirubins 1 and 2 did not exhibit the typical strong tendency of bilirubin dimethyl esters to form intermolecular hydrogen bonds in non-polar solvents such as chloroform and benzene.

  DOI：

  10.1016/s0040-4020(01)80362-8