3-(methylideneamino)-N-methylpropionamide | 252048-03-6

• 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: 3-(methylideneamino)-N-methylpropionamide
• 英文别名: N-methyl-3-(methylideneamino)propanamide
• CAS: 252048-03-6
• 化学式: C₅H₁₀N₂O
• mdl: MFCD19220490
• 分子量: 114.147
• InChiKey: MJDVXGUYKNRDDA-UHFFFAOYSA-N

物化性质

• 密度：
  0.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  3-(methylideneamino)-N-methylpropionamide 在 4-二甲氨基吡啶 、 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 5.0h， 生成 1-benzoyl-3,5-dimethyltetrahydropyrimidin-4-one
  参考文献：
  名称：

  Enantioselective alkylation and protonation of prochiral enolates in the asymmetric synthesis of β-amino acids

  摘要：

  Achiral 1-benzoyl-3-methylperhydropyrimidin-4-one (1) was deemed a useful, potential precursor for the enantioselective synthesis of alpha-substituted beta-amino acids. Pyrimidinone 1 was prepared from inexpensive beta-aminopropanoic acid in 62% overall yield. Prochiral enolate derivative 1-Li was alkylated in good yield and moderate enantioselectivity in the presence of chiral amines (S)-8, (S,S)-9, (S,S)-10, or (-)-sparteine. The enantioselectivity of the alkylation process is highest in toluene as the solvent and in the presence of lithium bromide as additive. The racemic alkylated derivatives 2 and 3 were readily metallated with LDA to give prochiral enolates 2-Li and 3-Li, that were reprotonated with novel chiral phenolic acids (S)-11, (S,S)-12, (S)-13, and (S,S)-14 in moderate enantioselectivity in the case of 2-Li and good enantioselectivity in the case of 3-Li. The acid (6N HCl) hydrolysis of enantioenriched 2 and 3 proceeded in good yield and without racemization to afford alpha-alkyl-beta-amino acids 4 and 5, respectively. (C) 2003 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(03)00578-7
• 作为产物：
  描述：

  聚合甲醛 、 3-氨基-N-甲基丙酰胺盐酸盐 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 6.0h， 生成 3-(methylideneamino)-N-methylpropionamide
  参考文献：
  名称：

  Enantioselective alkylation and protonation of prochiral enolates in the asymmetric synthesis of β-amino acids

  摘要：

  Achiral 1-benzoyl-3-methylperhydropyrimidin-4-one (1) was deemed a useful, potential precursor for the enantioselective synthesis of alpha-substituted beta-amino acids. Pyrimidinone 1 was prepared from inexpensive beta-aminopropanoic acid in 62% overall yield. Prochiral enolate derivative 1-Li was alkylated in good yield and moderate enantioselectivity in the presence of chiral amines (S)-8, (S,S)-9, (S,S)-10, or (-)-sparteine. The enantioselectivity of the alkylation process is highest in toluene as the solvent and in the presence of lithium bromide as additive. The racemic alkylated derivatives 2 and 3 were readily metallated with LDA to give prochiral enolates 2-Li and 3-Li, that were reprotonated with novel chiral phenolic acids (S)-11, (S,S)-12, (S)-13, and (S,S)-14 in moderate enantioselectivity in the case of 2-Li and good enantioselectivity in the case of 3-Li. The acid (6N HCl) hydrolysis of enantioenriched 2 and 3 proceeded in good yield and without racemization to afford alpha-alkyl-beta-amino acids 4 and 5, respectively. (C) 2003 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(03)00578-7

文献信息

• X-ray Crystallographic Study of Substituted Perhydropyrimidinones. Extreme Changes in Ring Conformation
  作者：Yara Ramírez-Quirós、Margarita Balderas、Jaime Escalante、Delia Quintana、Itzell Gallardo、Domingo Madrigal、Elies Molins、Eusebio Juaristi

  DOI：10.1021/jo991297q

  日期：1999.11.1

  X-ray crystal structures of 20 differently substituted perhydropyrimidin-4-ones are presented. Analysis of these data reveal a remarkable conformational sensitivity of a six-membered ring to substitution. Thus half-chair; envelope, boat, twist-boat, and intermediate conformations are found for the six-membered heterocycle, providing evidence for a relatively flat conformational energy surface in this ring, interpretation of the preferred conformations is advanced in terms of steric interactions among substituents and, in some cases, as the result of particular conformational (A(1,3) strain, anomeric) effects.