N-Isobutylidenvalin | 13135-56-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-Isobutylidenvalin
• 英文别名: (E)-N-(2-Methylpropylidene)-L-valine；(2S)-3-methyl-2-(2-methylpropylideneamino)butanoic acid
• CAS: 13135-56-3
• 化学式: C₉H₁₇NO₂
• 分子量: 171.239
• InChiKey: NNSCFSWXZPTUGB-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  49.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-Isobutylidenvalin 、 苯甲酰氯 以 二氯甲烷 为溶剂， 生成 (2R,4S)-3-benzoyl-2,4-diisopropyloxazolidin-5-one 、 (2S,4S)-3-benzoyl-2,4-diisopropyloxazolidin-5-one
  参考文献：
  名称：

  3-Benzoyl-2-isopropyl-4-alkyloxazolidin-5-ones as Efficient and Inexpensive Sources of Enantiopure α,α-Dialkyl α-Amino Acids and α,β-Dialkyl α,β-Diaminopropionic Acids

  摘要：

  It is shown that the 3-benzoyl-2-isopropyl-4-alkyloxazolidin-5-ones (12), derived from isobutyraldehyde and alpha-amino acids are as efficient as, but more economical than, the corresponding tert-butyl compounds (9), as sources of enantiopure alpha,alpha-dialkylated alpha-amino acids (e.g., 21-23). In the absence of alkylating agents, the anions of (2R,4S)-12 and its enantiomer undergo a fragmentation-recombination process to generate (1S,2'R,4'S)-N-[1-(3-benzoyl-2-isopropyl-4-methyl-5-oxo-oxazolidin-4-yl)-2-methylpropyl]benzamide ((1S,2'R,4'S)-20), and its enantiomer. Acidic methanolysis of these condensation products provides access to alpha,beta-dialkylated alpha,beta-diaminopropionic acids [e.g., (2S,3S)-2,3-bisbenzoylamino-2,4-dimethylpentanoic acid methyl ester ((2S,3S)-24)).

  DOI：

  10.3987/com-04-10214
• 作为产物：
  描述：

  L-缬氨酸 、 异丁醛 在 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 N-Isobutylidenvalin
  参考文献：
  名称：

  3-Benzoyl-2-isopropyl-4-alkyloxazolidin-5-ones as Efficient and Inexpensive Sources of Enantiopure α,α-Dialkyl α-Amino Acids and α,β-Dialkyl α,β-Diaminopropionic Acids

  摘要：

  It is shown that the 3-benzoyl-2-isopropyl-4-alkyloxazolidin-5-ones (12), derived from isobutyraldehyde and alpha-amino acids are as efficient as, but more economical than, the corresponding tert-butyl compounds (9), as sources of enantiopure alpha,alpha-dialkylated alpha-amino acids (e.g., 21-23). In the absence of alkylating agents, the anions of (2R,4S)-12 and its enantiomer undergo a fragmentation-recombination process to generate (1S,2'R,4'S)-N-[1-(3-benzoyl-2-isopropyl-4-methyl-5-oxo-oxazolidin-4-yl)-2-methylpropyl]benzamide ((1S,2'R,4'S)-20), and its enantiomer. Acidic methanolysis of these condensation products provides access to alpha,beta-dialkylated alpha,beta-diaminopropionic acids [e.g., (2S,3S)-2,3-bisbenzoylamino-2,4-dimethylpentanoic acid methyl ester ((2S,3S)-24)).

  DOI：

  10.3987/com-04-10214

文献信息

• 3-Benzoyl-2-isopropyl-4-alkyloxazolidin-5-ones as Efficient and Inexpensive Sources of Enantiopure α,α-Dialkyl α-Amino Acids and α,β-Dialkyl α,β-Diaminopropionic Acids
  作者：Susana Rojas-Lima、Alejandro Alvarez-Hernandez、Omar Téllez-Zenteno、Heraclio López-Ruiz

  DOI：10.3987/com-04-10214

  日期：——

  It is shown that the 3-benzoyl-2-isopropyl-4-alkyloxazolidin-5-ones (12), derived from isobutyraldehyde and alpha-amino acids are as efficient as, but more economical than, the corresponding tert-butyl compounds (9), as sources of enantiopure alpha,alpha-dialkylated alpha-amino acids (e.g., 21-23). In the absence of alkylating agents, the anions of (2R,4S)-12 and its enantiomer undergo a fragmentation-recombination process to generate (1S,2'R,4'S)-N-[1-(3-benzoyl-2-isopropyl-4-methyl-5-oxo-oxazolidin-4-yl)-2-methylpropyl]benzamide ((1S,2'R,4'S)-20), and its enantiomer. Acidic methanolysis of these condensation products provides access to alpha,beta-dialkylated alpha,beta-diaminopropionic acids [e.g., (2S,3S)-2,3-bisbenzoylamino-2,4-dimethylpentanoic acid methyl ester ((2S,3S)-24)).