3-Isopropyl-4-methoxycarbonyl-2-methyl-4-isoxazoline | 140116-65-0

• 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: 3-Isopropyl-4-methoxycarbonyl-2-methyl-4-isoxazoline
• 英文别名: methyl 2-methyl-3-propan-2-yl-3H-1,2-oxazole-4-carboxylate
• CAS: 140116-65-0
• 化学式: C₉H₁₅NO₃
• 分子量: 185.223
• InChiKey: TYYGKNINUVUPBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (Z)-N,2-dimethylpropan-1-imine oxide 、 丙炔酸甲酯 以 乙醚 为溶剂， 反应 12.0h， 生成 5-异噻唑羧酸,2,3-二氢-2-甲基-3-(1-甲基乙基)-,甲基酯 、 3-Isopropyl-4-methoxycarbonyl-2-methyl-4-isoxazoline
  参考文献：
  名称：

  Steric effects on regioselectivity in 1.3-Dipolar cycloaddition of C,N-dialyl nitrones with acceptor-substituted alkynes

  摘要：

  The 1.3 dipolar cycloaddition of alkynes 4-6 with acyclic nitrones 1-3, 23 and 24 as well as with cyclic nitrones 27 is studied. As was found for the reaction of the aldonitrones 1-3 an increased portion of 5-regioisomers is formed with increasing steric demand of either of the two substituents, the C-alkyl substituent R2 and the N-alkyl substituent R1. Thus the conclusion is drawn that cycloaddition of 1-3 proceeds not only via transition states arising from Z-nitrones but also via transition states developing from E-nitrones, although in the ground-state the Z-isomer is favored to a considerable extent. In this context steric destabilization of the transition states is discussed qualitatively.

  DOI：

  10.1016/s0040-4020(01)88127-8