benzyl 1-phenyl-1,4-dihydrospiro[indazole-5,4'-piperidine]-1'-carboxylate | 1356928-25-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: benzyl 1-phenyl-1,4-dihydrospiro[indazole-5,4'-piperidine]-1'-carboxylate
• CAS: 1356928-25-0
• 化学式: C₂₅H₂₅N₃O₂
• 分子量: 399.492
• InChiKey: AAZBWEPPVJOIEW-UHFFFAOYSA-N

物化性质

• 沸点：
  576.0±50.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.86
• 重原子数：
  30.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  47.36
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  9-氧代-3-氮杂螺[5.5]-7-十一烯-3-羧酸苄酯 在 溶剂黄146 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 23.0h， 生成 benzyl 1-phenyl-1,4-dihydrospiro[indazole-5,4'-piperidine]-1'-carboxylate
  参考文献：
  名称：

  Synthesis of 7-Oxo-dihydrospiro[indazole-5,4′-piperidine] Acetyl-CoA Carboxylase Inhibitors

  摘要：

  Synthesis of oxo-dihydrospiroindazole-based acetyl-CoA carboxylase (ACC) inhibitors is reported. The dihydrospiroindazoles were assembled in a regioselective manner in six steps from substituted hydrazines and protected 4-formylpiperidine. Enhanced regioselectivity in the condensation between a keto enamine and substituted hydrazines was observed when using toluene as the solvent, leading to selective formation of 1-substituted spiroindazoles. The 2-substituted spiroindazoles were formed selectively from alkyl hydrazones by ring closure with Vilsmeier reagent. The key step in the elaboration to the final products is the conversion of an intermediate olefin to the desired ketone through elimination of HBr from an O-methyl bromohydrin. This methodology enabled the synthesis of each desired regioisomer on 50-75 g scale with minimal purification. Acylation of the resultant spirocyclic amines provided potent ACC inhibitors.

  DOI：

  10.1021/jo202377g