1-benzoyl-2(R)-tert-butyl-3,5(S),6(S)-trimethylperhydropyrimidin-4-one | 139243-63-3

• 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: 1-benzoyl-2(R)-tert-butyl-3,5(S),6(S)-trimethylperhydropyrimidin-4-one
• 英文别名: (2R,5S,6S)-1-benzoyl-2-tert-butyl-3,5,6-trimethyl-1,3-diazinan-4-one
• CAS: 139243-63-3
• 化学式: C₁₈H₂₆N₂O₂
• 分子量: 302.417
• InChiKey: YMRVYGJHBSSZFW-GDZNZVCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 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-2(R)-tert-butyl-3,5(S),6(S)-trimethylperhydropyrimidin-4-one 在 盐酸 作用下， 反应 6.0h， 以52%的产率得到(2S,3S)-3-amino-2-methyl butyric acid
  参考文献：
  名称：

  Enantioselective synthesis of .beta.-amino acids. 2. Preparation of the like stereoisomers of 2-methyl- and 2-benzyl-3-aminobutanoic acid

  摘要：

  An improved procedure for the preparation of (R)- and (S)-3-aminobutanoic acids (2a) through diastereomer separation of the corresponding (1'S)-N-phenethyl derivatives 1 is reported. From 2a, the four possible stereisomeric perhydropyrimidin-4-ones 4 were prepared through the amide 2c and the Schiff base 3. In the cyclization of 3, the cis products 4 predominate ca. 95.5. These heterocycles can be alkylated (LDA, RX), as demonstrated by methylation and benzylation, with formation of a single diastereoisomer (5, 6). Hydrolysis (6 N aqueous HCl) of these 5,6-dialkylperhydropyrimidin-4-ones leads to the free amino acids 7-10.

  DOI：

  10.1021/jo00034a037
• 作为产物：
  描述：

  (S)-3-<(2,2'-dimethylpropylidene)amino>-N-methylbutanamide 在 4-二甲氨基吡啶 、 lithium diisopropyl amide 作用下， 以 甲苯 为溶剂， 反应 26.08h， 生成 1-benzoyl-2(R)-tert-butyl-3,5(S),6(S)-trimethylperhydropyrimidin-4-one
  参考文献：
  名称：

  Enantioselective synthesis of .beta.-amino acids. 2. Preparation of the like stereoisomers of 2-methyl- and 2-benzyl-3-aminobutanoic acid

  摘要：

  An improved procedure for the preparation of (R)- and (S)-3-aminobutanoic acids (2a) through diastereomer separation of the corresponding (1'S)-N-phenethyl derivatives 1 is reported. From 2a, the four possible stereisomeric perhydropyrimidin-4-ones 4 were prepared through the amide 2c and the Schiff base 3. In the cyclization of 3, the cis products 4 predominate ca. 95.5. These heterocycles can be alkylated (LDA, RX), as demonstrated by methylation and benzylation, with formation of a single diastereoisomer (5, 6). Hydrolysis (6 N aqueous HCl) of these 5,6-dialkylperhydropyrimidin-4-ones leads to the free amino acids 7-10.

  DOI：

  10.1021/jo00034a037