3-[2-Hydroxy-1-methyl-prop-(E)-ylideneamino]-butan-2-one | 115152-68-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-[2-Hydroxy-1-methyl-prop-(E)-ylideneamino]-butan-2-one
• 英文别名: 3-[(E)-(3-Hydroxybutan-2-ylidene)amino]butan-2-one；3-(3-hydroxybutan-2-ylideneamino)butan-2-one
• CAS: 115152-68-6
• 化学式: C₈H₁₅NO₂
• 分子量: 157.213
• InChiKey: WMZYZISESWKMQW-UHFFFAOYSA-N

物化性质

• 沸点：
  225.8±25.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  49.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-羟基-2-丁酮 在 乙酸铵 作用下， 以 水 为溶剂， 生成 2,4,5-三甲基恶唑 、 2,4,5-三甲基-3-唑啉 、 川芎嗪 、 2-(1-hydroxyethyl)-2,4,5-trimethyl-3-oxazoline 、 (E)-5-Hydroxy-3,4-dimethyl-hex-3-en-2-one 、 3-[2-Hydroxy-1-methyl-prop-(E)-ylideneamino]-butan-2-one
  参考文献：
  名称：

  Mechanistic Studies of 2-(1-Hydroxyethyl)-2,4,5-trimethyl-3- oxazoline Formation under Low Temperature in 3-Hydroxy-2-butanone/Ammonium Acetate Model Systems

  摘要：

  Volatile compounds formed from the reaction of 3-hydroxy-2-butanone/ammonium acetate at 25, 55 and 85 degrees C were investigated. Six compounds were characterized by gas chromatography-mass spectrometry (EI and CI). Among the volatile compounds identified, an interesting intermediate compound, 2-(1-hydroxyethyl)-2,4,5-trimethyl-3-oxazoline, was found. N-15-Labeled ammonium acetate was used to confirm the structure of 2-(P-hydroxyethyl)-2,4,5-trimethyl-3-oxazoline. The formation pathway of these volatile compounds was proposed. In these model systems, 2-(1-hydroxyethyl)-2,4,5-trimethyl-3-oxazoline was formed at the reaction temperature below 25 degrees C. On the other hand, tetramethylpyrazine was the major component when the reaction temperature was higher than 85 degrees C. The amounts of 2-(1-hydroxyethyl)-2,4,5-trimethyl-3-oxazoline and tetramethylpyrazine increased linearly with the increasing heating time at 55 degrees C. Protic solvents did not promote 2-(1-hydroxyethyl)-2,4,5-trimethyl-3-oxazoline formation but did favor the formation of tetramethylpyrazine. A kinetic study of 2-(1-hydroxyethyl)-2,4,5-trimethyl-3-oxazoline formation was also performed, and the activation energy was found to be 16.5 kcal/mol.

  DOI：

  10.1021/jf960734o

文献信息

• Mechanistic Studies of 2-(1-Hydroxyethyl)-2,4,5-trimethyl-3- oxazoline Formation under Low Temperature in 3-Hydroxy-2-butanone/Ammonium Acetate Model Systems
  作者：Hui-Yin Fu、Chi-Tang Ho

  DOI：10.1021/jf960734o

  日期：1997.5.1

  Volatile compounds formed from the reaction of 3-hydroxy-2-butanone/ammonium acetate at 25, 55 and 85 degrees C were investigated. Six compounds were characterized by gas chromatography-mass spectrometry (EI and CI). Among the volatile compounds identified, an interesting intermediate compound, 2-(1-hydroxyethyl)-2,4,5-trimethyl-3-oxazoline, was found. N-15-Labeled ammonium acetate was used to confirm the structure of 2-(P-hydroxyethyl)-2,4,5-trimethyl-3-oxazoline. The formation pathway of these volatile compounds was proposed. In these model systems, 2-(1-hydroxyethyl)-2,4,5-trimethyl-3-oxazoline was formed at the reaction temperature below 25 degrees C. On the other hand, tetramethylpyrazine was the major component when the reaction temperature was higher than 85 degrees C. The amounts of 2-(1-hydroxyethyl)-2,4,5-trimethyl-3-oxazoline and tetramethylpyrazine increased linearly with the increasing heating time at 55 degrees C. Protic solvents did not promote 2-(1-hydroxyethyl)-2,4,5-trimethyl-3-oxazoline formation but did favor the formation of tetramethylpyrazine. A kinetic study of 2-(1-hydroxyethyl)-2,4,5-trimethyl-3-oxazoline formation was also performed, and the activation energy was found to be 16.5 kcal/mol.