β--N-methyl-propionamide | 131932-57-5

• 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: β--N-methyl-propionamide
• 英文别名: 3-(2,2-dimethylpropylideneamino)-N-methylpropanamide
• CAS: 131932-57-5
• 化学式: C₉H₁₈N₂O
• 分子量: 170.255
• InChiKey: MAJKCUNDXHBHPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.24
• 重原子数：
  12.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  41.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  β--N-methyl-propionamide 在 偶氮二异丁腈 、 三丁基氯化锡 、 sodium cyanoborohydride 作用下， 以 甲苯 为溶剂， 生成 rac-1-benzoyl-2-(tert-butyl)tetrahydro-3-methylpyrimidin-4(1H)-one
  参考文献：
  名称：

  1,3-Asymmetric Induction via 1,5-Hydrogen Atom Translocation Reactions. Highly Enantioselective Synthesis of β-Substituted β-Amino Acids

  摘要：

  DOI：

  10.1021/ja961484v
• 作为产物：
  描述：

  3-氨基-n-甲基丙酰胺 、 特戊醛 生成 β--N-methyl-propionamide
  参考文献：
  名称：

  1,3-Asymmetric Induction via 1,5-Hydrogen Atom Translocation Reactions. Highly Enantioselective Synthesis of β-Substituted β-Amino Acids

  摘要：

  DOI：

  10.1021/ja961484v

文献信息

• Asymmetric synthesis of .beta.-amino acids. 1. Highly diastereoselective addition of a racemic .beta.-alanine enolate derivative to electrophiles
  作者：Eusebio Juaristi、Delia Quintana、Bernd Lamatsch、Dieter Seebach

  DOI：10.1021/jo00007a053

  日期：1991.3

  beta-Alanine, an inexpensive alpha-amino acid, was converted into the 2-tert-butylperhydropyrimidin-4-one derivative 2, which can be alkylated with high diastereoselectivity via the corresponding enolate. The high stereoselectivity observed for the reaction of 2-Li with electrophiles seems to be due to steric hindrance generated by an axial disposition of the tert-butyl group at C(2), which directs addition from the enolate face opposite to this group. The hydrolysis of the resulting adducts proceeds with 6 N hydrochloric acid to afford alpha-substituted beta-amino acids in good yields. These results pave the road to the development of a new asymmetric synthesis of enantiomerically pure alpha-substituted beta-amino acids.