cyclohexyl (3S)-methyl-N-p-toluenesulfonylaziridin-(2S)-carboxylate | 219738-98-4

• 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: cyclohexyl (3S)-methyl-N-p-toluenesulfonylaziridin-(2S)-carboxylate
• 英文别名: cyclohexyl (2S,3S)-3-methyl-1-(4-methylphenyl)sulfonylaziridine-2-carboxylate
• CAS: 219738-98-4
• 化学式: C₁₇H₂₃NO₄S
• 分子量: 337.44
• InChiKey: BENHVYFZNZKYKS-VKCAHTQSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  71.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  cyclohexyl (3S)-methyl-N-p-toluenesulfonylaziridin-(2S)-carboxylate 在 N,N-二甲基丙烯基脲 、 samarium (III) iodide 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以70%的产率得到cyclohexyl 2-iodo-3-(p-toluenesulfonamido)butanoate
  参考文献：
  名称：

  Deprotection of Sulfonyl Aziridines

  摘要：

  The deprotection of the chiral N-sulfonyl aziridines 1-3 has been studied under different desulfonylation conditions. Two methods for the efficient deprotection of 2-benzyl-, 2-phenyl-, and 2-carboxyl-N-sulfonylaziridines were found. The desulfonylation with lithium and a catalytic amount of di-tert-butyl biphenyl in THF at -78 degrees C led to the corresponding NH aziridines with yields up to 85%. Alternatively, the desulfonylation could be carried out with magnesium in methanol under ultrasonic conditions. The latter proved to be avery mild method and afforded the desulfonylated aziridines with yields up to 75%, even when the 2-phenyl substituted aziridine 2 was the studied substrate. Furthermore, in all the cases studied, no racemization was observed in the chiral center of the aziridines.

  DOI：

  10.1021/jo9815296
• 作为产物：
  描述：

  L-threonine cyclohexy ester hydrochloride 在 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 cyclohexyl (3S)-methyl-N-p-toluenesulfonylaziridin-(2S)-carboxylate
  参考文献：
  名称：

  Deprotection of Sulfonyl Aziridines

  摘要：

  The deprotection of the chiral N-sulfonyl aziridines 1-3 has been studied under different desulfonylation conditions. Two methods for the efficient deprotection of 2-benzyl-, 2-phenyl-, and 2-carboxyl-N-sulfonylaziridines were found. The desulfonylation with lithium and a catalytic amount of di-tert-butyl biphenyl in THF at -78 degrees C led to the corresponding NH aziridines with yields up to 85%. Alternatively, the desulfonylation could be carried out with magnesium in methanol under ultrasonic conditions. The latter proved to be avery mild method and afforded the desulfonylated aziridines with yields up to 75%, even when the 2-phenyl substituted aziridine 2 was the studied substrate. Furthermore, in all the cases studied, no racemization was observed in the chiral center of the aziridines.

  DOI：

  10.1021/jo9815296