1-benzoyl-3,5(R),6(S)-trimethylperhydropyrimidin-4-one | 147034-48-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-benzoyl-3,5(R),6(S)-trimethylperhydropyrimidin-4-one
• 英文别名: (5R,6S)-1-benzoyl-3,5,6-trimethyl-1,3-diazinan-4-one
• CAS: 147034-48-8
• 化学式: C₁₄H₁₈N₂O₂
• 分子量: 246.309
• InChiKey: FZJJHCQRZCDVMQ-MNOVXSKESA-N

物化性质

• 沸点：
  422.7±38.0 °C(predicted)
• 密度：
  1.109±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-benzoyl-3,5(R),6(S)-trimethylperhydropyrimidin-4-one 在 盐酸 作用下， 反应 6.0h， 以81.7%的产率得到(2R,3S)-β^2,3hAla(αMe)-OH
  参考文献：
  名称：

  Enantioselective synthesis of .beta.-amino acids. 4. 1,2 Asymmetric induction in the alkylation of 1-benzoyl-3,6(S)-dimethylperhydropyrimidin-4-one. Preparation of the like and unlike stereoisomers of 2-methyl- and 2-benzyl-3(S)-aminobutanoic acid

  摘要：

  The title perhydropyrimidin-4-one (S)-4 was prepared from (S)-3-aminobutanoic acid via the Schiff base (S)-8. This heterocycle was alkylated (LDA, methyl iodide, or benzyl bromide) to afford the like and unlike diastereomeric products in a 80:20 ratio. Separation and hydrolysis (6 N aqueous HCl) of these 5,6-dialkylperhydropyrimidin-4-ones leads to the free, enantiomerically pure, amino acids 11-14.

  DOI：

  10.1021/jo00060a051
• 作为产物：
  描述：

  (S)-3-(methylideneamino)-N-methylbutanamide 在 4-二甲氨基吡啶 、 正丁基锂 、 二异丙胺 作用下， 以 苯 为溶剂， 反应 8.08h， 生成 1-benzoyl-3,5(R),6(S)-trimethylperhydropyrimidin-4-one
  参考文献：
  名称：

  Enantioselective synthesis of .beta.-amino acids. 4. 1,2 Asymmetric induction in the alkylation of 1-benzoyl-3,6(S)-dimethylperhydropyrimidin-4-one. Preparation of the like and unlike stereoisomers of 2-methyl- and 2-benzyl-3(S)-aminobutanoic acid

  摘要：

  The title perhydropyrimidin-4-one (S)-4 was prepared from (S)-3-aminobutanoic acid via the Schiff base (S)-8. This heterocycle was alkylated (LDA, methyl iodide, or benzyl bromide) to afford the like and unlike diastereomeric products in a 80:20 ratio. Separation and hydrolysis (6 N aqueous HCl) of these 5,6-dialkylperhydropyrimidin-4-ones leads to the free, enantiomerically pure, amino acids 11-14.

  DOI：

  10.1021/jo00060a051

文献信息

• Enantioselective synthesis of .beta.-amino acids. 4. 1,2 Asymmetric induction in the alkylation of 1-benzoyl-3,6(S)-dimethylperhydropyrimidin-4-one. Preparation of the like and unlike stereoisomers of 2-methyl- and 2-benzyl-3(S)-aminobutanoic acid
  作者：Eusebio Juaristi、Jaime Escalante

  DOI：10.1021/jo00060a051

  日期：1993.4

  The title perhydropyrimidin-4-one (S)-4 was prepared from (S)-3-aminobutanoic acid via the Schiff base (S)-8. This heterocycle was alkylated (LDA, methyl iodide, or benzyl bromide) to afford the like and unlike diastereomeric products in a 80:20 ratio. Separation and hydrolysis (6 N aqueous HCl) of these 5,6-dialkylperhydropyrimidin-4-ones leads to the free, enantiomerically pure, amino acids 11-14.