2-(2'-ethoxycarbonyl)acryloyl-3-phenyl-l-menthopyrazole | 221482-76-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(2'-ethoxycarbonyl)acryloyl-3-phenyl-l-menthopyrazole
• 英文别名: ethyl (E)-4-[(4R,7S)-4-methyl-3-phenyl-7-propan-2-yl-4,5,6,7-tetrahydroindazol-2-yl]-4-oxobut-2-enoate
• CAS: 221482-76-4
• 化学式: C₂₃H₂₈N₂O₃
• 分子量: 380.487
• InChiKey: IHPWQCOYJWPONH-UKBCRRFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  61.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,3-丁二烯 、 2-(2'-ethoxycarbonyl)acryloyl-3-phenyl-l-menthopyrazole 在 zinc(II) chloride 作用下， 以 甲苯 为溶剂， 反应 20.0h， 生成 (1'R,6'R)-2-(6'-ethoxycarbonyl-3'-cyclohexenecarbonyl)-3-phenyl-l-menthopyrazole 、 ethyl (1S,6S)-6-[(4R,7S)-4-methyl-3-phenyl-7-propan-2-yl-4,5,6,7-tetrahydroindazole-2-carbonyl]cyclohex-3-ene-1-carboxylate
  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
• 作为产物：
  描述：

  富马酸单乙酯 、 3-苯基-l-薄荷吡唑 在 氯化亚砜 作用下， 以55%的产率得到2-(2'-ethoxycarbonyl)acryloyl-3-phenyl-l-menthopyrazole
  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