1-(3',4'-dimethyl-3'-cyclohexenecarbonyl)-3,5-dimethylpyrazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(3',4'-dimethyl-3'-cyclohexenecarbonyl)-3,5-dimethylpyrazole
• 英文别名: (3,4-Dimethylcyclohex-3-en-1-yl)-(3,5-dimethylpyrazol-1-yl)methanone
• 化学式: C₁₄H₂₀N₂O
• 分子量: 232.326
• InChiKey: CJHRLDGJBZSEJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,3-二甲基-1,3-丁二烯 、 1-(3,5-二甲基吡唑-1-基)丙-2-烯-1-酮 在 magnesium bromide 作用下， 以 甲苯 为溶剂， 32.0 ℃ 、100.0 kPa 条件下， 以90%的产率得到1-(3',4'-dimethyl-3'-cyclohexenecarbonyl)-3,5-dimethylpyrazole
  参考文献：
  名称：

  Diastereoselective Diels−Alder Reaction of 2-(α,β-Unsaturated)acyl-3-phenyl-l-menthopyrazoles

  摘要：

  The reaction of 2-(alpha,beta-unsaturated)acyl-3-phenyl-l-menthopyrazoles (9) with dienes gave Diels-Alder adducts in good yield. The addition of MgBr2. OEt2 or ZnCl2 accelerated these reactions through the formation of chelating bonds such as N ... Mg ... O=C or N ... Zn ... O=C. The structural fixation by these catalysts also promoted the endo and diastereoselectivities of the Diels-Alder addition on the Re-face of the dienophiles. These results were supported by PM3 calculations, in which the heats of formation of the transition states anticipated the remarkable differences between the Re- and Si-facial attacks of the dienes.

  DOI：

  10.1021/jo981255m