(S)-2-(S)-Aziridin-2-yl-N-methoxy-N-methyl-3-phenyl-propionamide | 349148-61-4

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: (S)-2-(S)-Aziridin-2-yl-N-methoxy-N-methyl-3-phenyl-propionamide
• CAS: 349148-61-4
• 化学式: C₁₃H₁₈N₂O₂
• 分子量: 234.298
• InChiKey: XVCJVXXATCERPP-NWDGAFQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.84
• 重原子数：
  17.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  51.48
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S)-2-(S)-Aziridin-2-yl-N-methoxy-N-methyl-3-phenyl-propionamide 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 4.0h， 生成 (S)-3-Phenyl-2-((S)-1-trityl-aziridin-2-yl)-propionaldehyde
  参考文献：
  名称：

  Synthesis of Optically Active 2-Alkyl-3,4-iminobutanoic Acids. β-Amino Acids Containing an Aziridine Heterocycle

  摘要：

  All four stereoisomers of 2-alkyl-3,4-iminobutanoic acid, a novel class of beta -amino acids bearing a chemically versatile aziridine ring, were synthesized starting with aspartic acid. The synthetic strategy involves the introduction of an alkyl group at the beta -position of fully protected optically active aspartic acid followed by the construction of an aziridine ring making use of the alpha -carboxylate and alpha -amino groups. The alpha -carboxylate was reduced to the corresponding alcohol, which was then subjected to cyclization to form an aziridine ring with the N-protected amino group. Removal of the protection groups yielded the target compounds.

  DOI：

  10.1021/jo0014055
• 作为产物：
  描述：

  (3S,4S)-3-benzyl-4-(N-benzyloxycarbonylamino)-butyrolactone 在 palladium on activated charcoal 氢气 、 三甲基铝 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (S)-2-(S)-Aziridin-2-yl-N-methoxy-N-methyl-3-phenyl-propionamide
  参考文献：
  名称：

  Synthesis of Optically Active 2-Alkyl-3,4-iminobutanoic Acids. β-Amino Acids Containing an Aziridine Heterocycle

  摘要：

  All four stereoisomers of 2-alkyl-3,4-iminobutanoic acid, a novel class of beta -amino acids bearing a chemically versatile aziridine ring, were synthesized starting with aspartic acid. The synthetic strategy involves the introduction of an alkyl group at the beta -position of fully protected optically active aspartic acid followed by the construction of an aziridine ring making use of the alpha -carboxylate and alpha -amino groups. The alpha -carboxylate was reduced to the corresponding alcohol, which was then subjected to cyclization to form an aziridine ring with the N-protected amino group. Removal of the protection groups yielded the target compounds.

  DOI：

  10.1021/jo0014055