(4-methoxyphenyl) (2R)-1-[(1S)-1-phenylethyl]aziridine-2-carboxylate | 143833-48-1

• 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: (4-methoxyphenyl) (2R)-1-[(1S)-1-phenylethyl]aziridine-2-carboxylate
• CAS: 143833-48-1
• 化学式: C₁₈H₁₉NO₃
• 分子量: 297.354
• InChiKey: FDUWNPOTWAHJBP-JQKBXSLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  38.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  碳酸亚乙烯酯 、 (4-methoxyphenyl) (2R)-1-[(1S)-1-phenylethyl]aziridine-2-carboxylate 以 甲苯 为溶剂， 反应 0.5h， 以30%的产率得到(4-methoxyphenyl) (3aR,4R,6aS)-2-oxo-5-[(1S)-1-phenylethyl]-3a,4,6,6a-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-4-carboxylate
  参考文献：
  名称：

  Chiral synthesis of both enantiomers of 1,4-dideoxy-1,4-immolyxitol and 1,4-dideoxy-1,4-iminoribitol

  摘要：

  Reaction of 2,3-dibromopropionyl chloride with 4-methoxyphenol and (S)-1-methlbenzylamine yielded a 4:5 mixture of readily separable diastereomeric aziridine esters in an excellent yield. Both diastereomers, upon heating with vinylene carbonate, furnished four readily separable diastereomeric pyrrolidine esters, respectively, which were transformed into both enantiomers of 1,4-dideoxy-1,4-iminolyxitol and 1,4-dideoxy-1,4-iminoribitol.

  DOI：

  10.1016/s0957-4166(00)80499-1
• 作为产物：
  描述：

  2,3-二溴丙酰氯 、 (S)-(-)- α-甲基苄胺 、 4-甲氧基苯酚 在 三乙胺 作用下， 生成 (4-methoxyphenyl) (2S)-1-[(1S)-1-phenylethyl]aziridine-2-carboxylate 、 (4-methoxyphenyl) (2R)-1-[(1S)-1-phenylethyl]aziridine-2-carboxylate
  参考文献：
  名称：

  Chiral synthesis of both enantiomers of 1,4-dideoxy-1,4-immolyxitol and 1,4-dideoxy-1,4-iminoribitol

  摘要：

  Reaction of 2,3-dibromopropionyl chloride with 4-methoxyphenol and (S)-1-methlbenzylamine yielded a 4:5 mixture of readily separable diastereomeric aziridine esters in an excellent yield. Both diastereomers, upon heating with vinylene carbonate, furnished four readily separable diastereomeric pyrrolidine esters, respectively, which were transformed into both enantiomers of 1,4-dideoxy-1,4-iminolyxitol and 1,4-dideoxy-1,4-iminoribitol.

  DOI：

  10.1016/s0957-4166(00)80499-1

文献信息

• Chiral synthesis of both enantiomers of 1,4-dideoxy-1,4-immolyxitol and 1,4-dideoxy-1,4-iminoribitol
  作者：Seiichi Takano、Minoru Moriya、Kunio Ogasawara

  DOI：10.1016/s0957-4166(00)80499-1

  日期：1992.6

  Reaction of 2,3-dibromopropionyl chloride with 4-methoxyphenol and (S)-1-methlbenzylamine yielded a 4:5 mixture of readily separable diastereomeric aziridine esters in an excellent yield. Both diastereomers, upon heating with vinylene carbonate, furnished four readily separable diastereomeric pyrrolidine esters, respectively, which were transformed into both enantiomers of 1,4-dideoxy-1,4-iminolyxitol and 1,4-dideoxy-1,4-iminoribitol.