1,3-diphenyl-4,11-dihydrospiro[1H-pyrazolo[3,4-b]benzo[h]quinoline-4,3'-indolin]-2'-one | 1562075-98-2

• 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-diphenyl-4,11-dihydrospiro[1H-pyrazolo[3,4-b]benzo[h]quinoline-4,3'-indolin]-2'-one
• 英文别名: 13,15-diphenylspiro[14,15,17-triazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,8,12(16),13-heptaene-11,3'-1H-indole]-2'-one
• CAS: 1562075-98-2
• 化学式: C₃₃H₂₂N₄O
• 分子量: 490.564
• InChiKey: XDQMTBPRWFADFN-UHFFFAOYSA-N

物化性质

• 熔点：
  307-310 °C
• 沸点：
  768.0±60.0 °C(predicted)
• 密度：
  1.35±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  38
• 可旋转键数：
  2
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  59
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  靛红 、 1-萘胺 、 苯甲酰乙酸乙酯 、 苯肼 在 对甲苯磺酸 作用下， 以 neat (no solvent) 为溶剂， 反应 4.5h， 以65%的产率得到1,3-diphenyl-4,11-dihydrospiro[1H-pyrazolo[3,4-b]benzo[h]quinoline-4,3'-indolin]-2'-one
  参考文献：
  名称：

  A four-component synthesis of novel spiro[pyrazoloquinoline-oxindoles] under solvent-free conditions

  摘要：

  A domino reaction for the rapid and diverse synthesis of spiro[1H-pyrazolo[3,4-b]benzo[h]dihydroquinolin-4,3-indolin-2-ones] is reported. The synthesis represents a thermodynamically-favored four-component reaction between phenylhydrazine, isatins, naphthylamines, and 3-ketoesters giving the novel products in excellent yields under solvent-free conditions. Similar applications of anilines in place of naphthylamines have not led to formation of the expected 4-substituted pyrazolo[3,4-b]quinoline derivatives. The difference was ascribed to lower aromatic character of naphthylamines, with respect to anilines, which enables them to act easier as enamines in reaction with the postulated intermediates formed from condensation of isatins and the in situ generated pyrazolones. Surprisingly, 6-aminouracils in despite of their known enamine properties did not participate in reaction with isatins and pyrazolones, the merit of naphthylamines for this synthesis seems to be met by the favorable balance of their N- and C-nucleophilicity. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.01.025