(2RS,3RS)-4,4-dimethyl-2-(1-tert-butylsulfonyl-2-methyl-3-phenylaziridin-2-yl)-4,5-dihydrooxazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (2RS,3RS)-4,4-dimethyl-2-(1-tert-butylsulfonyl-2-methyl-3-phenylaziridin-2-yl)-4,5-dihydrooxazole
• 英文别名: 2-[(2S,3S)-1-tert-butylsulfonyl-2-methyl-3-phenylaziridin-2-yl]-4,4-dimethyl-5H-1,3-oxazole
• 化学式: C₁₈H₂₆N₂O₃S
• 分子量: 350.482
• InChiKey: KHIIKEFPQDYQNN-KEXXGOCASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  67.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2RS,3RS)-4,4-dimethyl-2-(1-tert-butylsulfonyl-2-methyl-3-phenylaziridin-2-yl)-4,5-dihydrooxazole 在 四甲基乙二胺 、 仲丁基锂 、 重水 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 反应 1.5h， 生成 2-[(2S,3S)-1-tert-butylsulfonyl-3-deuterio-2-methyl-3-phenylaziridin-2-yl]-4,4-dimethyl-5H-1,3-oxazole
  参考文献：
  名称：

  Synthesis and lithiation of oxazolinylaziridines: the N-substituent effect

  摘要：

  The preparation of N-substituted oxazolinylaziridines and their deprotonation to afford the corresponding aziridinyllithiums is described. The chemical and configurational stability of the lithiated species depends on the N-substituent on the aziridine ring. The trapping with carbonyl compounds of (R*,S*) configurated oxazolinylaziridines is an interesting route for the preparation of functionalised alpha,beta-aziridino-gamma-lactones. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.01.045
• 作为产物：
  描述：

  2-(1-chloroethyl)-4,4-dimethyl-2-oxazoline 、 (E)-N-benzylidene-2-methylpropane-2-sulfonamide 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以64%的产率得到(2RS,3RS)-4,4-dimethyl-2-(1-tert-butylsulfonyl-2-methyl-3-phenylaziridin-2-yl)-4,5-dihydrooxazole
  参考文献：
  名称：

  Synthesis and lithiation of oxazolinylaziridines: the N-substituent effect

  摘要：

  The preparation of N-substituted oxazolinylaziridines and their deprotonation to afford the corresponding aziridinyllithiums is described. The chemical and configurational stability of the lithiated species depends on the N-substituent on the aziridine ring. The trapping with carbonyl compounds of (R*,S*) configurated oxazolinylaziridines is an interesting route for the preparation of functionalised alpha,beta-aziridino-gamma-lactones. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.01.045