2-(3,5-dinitrophenyl)-4-isopropyl-4,5-dihydrooxazole | 1335200-05-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(3,5-dinitrophenyl)-4-isopropyl-4,5-dihydrooxazole
• 英文别名: 2-(3,5-Dinitrophenyl)-4-propan-2-yl-4,5-dihydro-1,3-oxazole；2-(3,5-dinitrophenyl)-4-propan-2-yl-4,5-dihydro-1,3-oxazole
• CAS: 1335200-05-9
• 化学式: C₁₂H₁₃N₃O₅
• 分子量: 279.252
• InChiKey: LGHPSUUQZQSYRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  DL-2-氨基-3-甲基-1-丁醇 在 偶氮二甲酸二异丙酯 、 三乙胺 、 三苯基膦 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 四氢呋喃 、 甲苯 、 乙腈 为溶剂， 反应 25.0h， 生成 2-(3,5-dinitrophenyl)-4-isopropyl-4,5-dihydrooxazole
  参考文献：
  名称：

  Phosphine-Catalyzed Heine Reaction

  摘要：

  Aziridines are important synthetic Intermediates which readily undergo ring-opening reactions. It is demonstrated that electron-rich phosphines are efficient catalysts for the regioselective rearrangement of N-acylaziridines to oxazolines. The reactions occur in excellent yield under neutral conditions. Evidence is provided for an addition/elimination mechanism by generation of a phosphonium intermediate. Similar intermediates may be useful for the development of alternate aziridine ring-opening processes and stereoselective synthesis with enantiopure phosphines.

  DOI：

  10.1021/ol202410v

文献信息

• Phosphine-Catalyzed Heine Reaction
  作者：Allen Martin、Kathleen Casto、William Morris、Jeremy B. Morgan

  DOI：10.1021/ol202410v

  日期：2011.10.21

  Aziridines are important synthetic Intermediates which readily undergo ring-opening reactions. It is demonstrated that electron-rich phosphines are efficient catalysts for the regioselective rearrangement of N-acylaziridines to oxazolines. The reactions occur in excellent yield under neutral conditions. Evidence is provided for an addition/elimination mechanism by generation of a phosphonium intermediate. Similar intermediates may be useful for the development of alternate aziridine ring-opening processes and stereoselective synthesis with enantiopure phosphines.