(R)-3-<(2,2'-dimethylpropylidene)amino>-N-methylbutanamide | 139243-56-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R)-3-<(2,2'-dimethylpropylidene)amino>-N-methylbutanamide
• 英文别名: (R)-3-[(2,2'-dimethylpropylidene)amino]-N-methylbutanamide；Butanamide, 3-[(2,2-dimethylpropylidene)amino]-N-methyl-, (R)-；(3R)-3-(2,2-dimethylpropylideneamino)-N-methylbutanamide
• CAS: 139243-56-4
• 化学式: C₁₀H₂₀N₂O
• 分子量: 184.282
• InChiKey: BGOHGLDKVCBZDH-MRVPVSSYSA-N

物化性质

• 沸点：
  328.4±34.0 °C(Predicted)
• 密度：
  0.91±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-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(S)-tert-butyl-3,6(R)-dimethyl-5(R)-benzylperhydropyrimidin-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
• 作为产物：
  描述：

  特戊醛 、 (R)-3-aminobutanoic acid methyl ester 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 (R)-3-<(2,2'-dimethylpropylidene)amino>-N-methylbutanamide
  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

文献信息

• Enantioselective synthesis of .beta.-amino acids. 2. Preparation of the like stereoisomers of 2-methyl- and 2-benzyl-3-aminobutanoic acid
  作者：Eusebio Juaristi、Jaime Escalante、Bernd Lamatsch、Dieter Seebach

  DOI：10.1021/jo00034a037

  日期：1992.4

  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.