(1'S,2'S,4'S)-(2-bicyclo<2.2.1>hept-5'-ene-2'-carbonyl)-3-phenyl-l-menthopyrazole | 221482-81-1

• 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'S,2'S,4'S)-(2-bicyclo<2.2.1>hept-5'-ene-2'-carbonyl)-3-phenyl-l-menthopyrazole
• 英文别名: [(1S,2S,4S)-2-bicyclo[2.2.1]hept-5-enyl]-[(4R,7S)-4-methyl-3-phenyl-7-propan-2-yl-4,5,6,7-tetrahydroindazol-2-yl]methanone
• CAS: 221482-81-1
• 化学式: C₂₅H₃₀N₂O
• 分子量: 374.526
• InChiKey: GQINAOLOPRBWQT-RKNHFHLDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1'S,2'S,4'S)-(2-bicyclo<2.2.1>hept-5'-ene-2'-carbonyl)-3-phenyl-l-menthopyrazole 、 苯甲醇 在 三氟化硼乙醚 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以75%的产率得到benzyl (1'S,2'S,4'S)-bicyclo<2.2.1>hept-5-ene-2-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：

  环戊二烯 、 2-acryloyl-2-phenyl-l-menthopyrazole 在 zinc(II) chloride 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成 (1'R,2'R,4'R)-(2-bicyclo<2.2.1>hept-5'-ene-2'-carbonyl)-3-phenyl-l-menthopyrazole 、 (1'S,2'S,4'S)-(2-bicyclo<2.2.1>hept-5'-ene-2'-carbonyl)-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