isoxazoline N-oxide | 55055-07-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: isoxazoline N-oxide
• 英文别名: 2-Oxo-4,5-dihydro-1,2lambda~5~-oxazole；2-oxido-4,5-dihydro-1,2-oxazol-2-ium
• CAS: 55055-07-7
• 化学式: C₃H₅NO₂
• 分子量: 87.0782
• InChiKey: BRIFVTYYOOJQMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  6
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  38
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-iodo-3-nitropropane 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 反应 0.17h， 以20%的产率得到isoxazoline N-oxide
  参考文献：
  名称：

  Cycloaddition/Ring opening of 3-unsubstituted cyclic nitronates, isoxazoline and 5,6-dihydro-4H-1,2-oxazineN-oxides, as synthetic equivalents of functionalized nitrile oxides

  摘要：

  omega-Halo-alpha-nitropropane and -butane are cyclized with a base to form cyclic nitronates as labile 1,3-dipoles. They can be trapped by a variety of monosubstituted ethenes to give 3-(2-hydroxyethyl)isoxazolines or perhydroisoxazolo[2,3-b]o-oxazines depending upon the ring size of nitronates. The latter ring-fused heterocycles are transformed by treatment with an acid into 3-(3-hydroxypropyl)isoxazolines in good yields. Therefore, these cyclic nitronates are useful synthetic equivalents of functionalized nitrile oxides. Isolation of 5,6-dihydro-4H-1,2-oxazine N-oxide and their regio- and stereoselective cycloadditions are also discussed. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01903-0