1-(3'-phenyl-2'-isoxazoline-5'-carbonyl)-3,5-dimethylpyrazole

• 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: 1-(3'-phenyl-2'-isoxazoline-5'-carbonyl)-3,5-dimethylpyrazole
• 英文别名: 3-Phenyl-4,5-dihydroisoxazole-5-yl 3,5-dimethyl-1H-pyrazole-1-yl ketone；(3,5-dimethylpyrazol-1-yl)-(3-phenyl-4,5-dihydro-1,2-oxazol-5-yl)methanone
• 化学式: C₁₅H₁₅N₃O₂
• 分子量: 269.303
• InChiKey: COXRZERCQPHQOC-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：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  benzohydroximoyl chloride 、 1-(3,5-二甲基吡唑-1-基)丙-2-烯-1-酮 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以90%的产率得到1-(3'-phenyl-2'-isoxazoline-5'-carbonyl)-3,5-dimethylpyrazole
  参考文献：
  名称：

  Diastereoselective 1,3-Dipolar Cycloaddition of 2-(a,b-Unsaturated) Acyl-3-phenyl-l-menthopyrazoles

  摘要：

  The 1,3-dipolar cycloadducts of N-(alpha,beta-unsaturated) acylpyrazoles (2) with benzonitrile oxide or nitrones were afforded in good yield. in the cases of nitrones, the addition of MgBr2 or ZnBr2 promoted the stereoselectivity as well as the acceleration of the reaction rate. In the reaction of 2f and 2g, the big jump on the diastereoselectivity was accomplished by the addition of MgBr2, and (3'S,4'R,5'S)-8 was obtained as optically pure form in over 90% yield. These isoxazolidinecarbonylpyrazoles were converted into azetidinones in moderate yield with the retention of their stereo structures.

  DOI：

  10.3987/com-96-s19

文献信息

• Diastereoselective 1,3-Dipolar Cycloaddition of 2-(a,b-Unsaturated) Acyl-3-phenyl-l-menthopyrazoles
  作者：Choji Kashima、Katsumi Takahashi、Iwao Fukuchi、Kiyoshi Fukusaka

  DOI：10.3987/com-96-s19

  日期：——

  The 1,3-dipolar cycloadducts of N-(alpha,beta-unsaturated) acylpyrazoles (2) with benzonitrile oxide or nitrones were afforded in good yield. in the cases of nitrones, the addition of MgBr2 or ZnBr2 promoted the stereoselectivity as well as the acceleration of the reaction rate. In the reaction of 2f and 2g, the big jump on the diastereoselectivity was accomplished by the addition of MgBr2, and (3'S,4'R,5'S)-8 was obtained as optically pure form in over 90% yield. These isoxazolidinecarbonylpyrazoles were converted into azetidinones in moderate yield with the retention of their stereo structures.