1-phenyl-3-propyl-4,11-dihydrospiro[1H-pyrazolo[3,4-b]benzo[f]quinoline-4,3'-indolin]-2'-one | 1562076-02-1

• 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-phenyl-3-propyl-4,11-dihydrospiro[1H-pyrazolo[3,4-b]benzo[f]quinoline-4,3'-indolin]-2'-one
• 英文别名: 13-phenyl-15-propylspiro[11,13,14-triazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,8,12(16),14-heptaene-17,3'-1H-indole]-2'-one
• CAS: 1562076-02-1
• 化学式: C₃₀H₂₄N₄O
• 分子量: 456.547
• InChiKey: SWAVESOBWMGRGQ-UHFFFAOYSA-N

物化性质

• 熔点：
  >310 °C
• 沸点：
  691.8±55.0 °C(predicted)
• 密度：
  1.33±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  35
• 可旋转键数：
  3
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.13
• 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 、 丁酰乙酸乙酯 、 苯肼 、 2-萘胺 在 对甲苯磺酸 作用下， 以 neat (no solvent) 为溶剂， 反应 2.33h， 以81%的产率得到1-phenyl-3-propyl-4,11-dihydrospiro[1H-pyrazolo[3,4-b]benzo[f]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

文献信息

• Preparation of spirooxindoles catalyzed by nano-Co3S4 under microwave irradiations
  作者：Sheida Khojasteh-Khosro、Hossein Shahbazi-Alavi

  DOI：10.1177/1747519819841791

  日期：2019.3

  efficient and rapid method is used for the synthesis of 10-methyl-8H-spiro[benzo[5,6]chromeno[2,3-c]pyrazole-11,3′-indol]-2′(1′H)-one and 8-methyl-10-phenyl-10,11-dihydrospiro[pyrazolo[3,4-b]benzo[h]quinolin-7,3′-indol]-2′(1′H)-one by a four-component reactions of phenylhydrazine or hydrazine hydrate, isatins, ketoesters, and naphthylamine or 2-naphthol using nano-Co3S4 under microwave irradiation.

  一种高效快速合成10-甲基-8H-螺[苯并[5,6]色基[2,3-c]吡唑-11,3'-吲哚]-2'(1'H)的方法-one 和 8-methyl-10-phenyl-10,11-dihydrospiro[pyrazolo[3,4-b]benzo[h]quinolin-7,3'-indol]-2'(1'H)-one在微波辐射下使用纳米 Co3S4 进行苯肼或水合肼、靛红、酮酯和萘胺或 2-萘酚的四组分反应。