6'-amino-3'-methyl-2-oxo-1'-phenyl-4'H-spiro[1-ethylindoline-3,4'-pyrano[2,3-c]pyrazole]-5'-carbonitrile | 845661-53-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6'-amino-3'-methyl-2-oxo-1'-phenyl-4'H-spiro[1-ethylindoline-3,4'-pyrano[2,3-c]pyrazole]-5'-carbonitrile
• 英文别名: 6'-amino-1-ethyl-3'-methyl-2-oxo-1'-phenyl-1,2-dihydro-1'H-spiro[indole-3,4'-pyrano[2,3-c]pyrazole]-5'-carbonitrile；6'-amino-1-ethyl-3'-methyl-2-oxo-1'-phenylspiro[indole-3,4'-pyrano[2,3-c]pyrazole]-5'-carbonitrile
• CAS: 845661-53-2
• 化学式: C₂₃H₁₉N₅O₂
• 分子量: 397.436
• InChiKey: LHYCJLHQBCUQPC-UHFFFAOYSA-N

物化性质

• 沸点：
  715.3±60.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  30
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  97.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-乙基-1H-吲哚-2,3-二酮 、 3-methyl-1-phenyl-1,5-dihydro-4H-pyrazol-4-one 、 丙二腈 在 cesium fluoride 作用下， 以 乙醇 为溶剂， 反应 0.05h， 以98%的产率得到6'-amino-3'-methyl-2-oxo-1'-phenyl-4'H-spiro[1-ethylindoline-3,4'-pyrano[2,3-c]pyrazole]-5'-carbonitrile
  参考文献：
  名称：

  CsF促进了室温下乙醇中螺氧杂吲哚-吡喃环杂环的快速合成

  摘要：

  描述了一种新型的，多功能的，直接的合成策略，用于构建功能化螺氧杂吲哚-吡喃环杂环。该程序基于室温下在乙醇中，由CsF促进的快速串联串联的Isatin，丙二腈和4-羟基香豆素/巴比妥酸/吡唑啉酮的Knoevenagel-Michael-环缩合反应。该方法具有多种优势，例如操作简便，在短反应时间内（3-25分钟）即可获得出色的收率，以及产物的简单分离。CsF兼具碱和羰基活化剂的作用。

  DOI：

  10.1002/jhet.3846

文献信息

• Ultrasound promoted green synthesis of spiro[pyrano[2,3-c]pyrazoles] as antioxidant agents
  作者：Anshu Dandia、Deepti Saini、Sumit Bhaskaran、Dinesh Kumar Saini

  DOI：10.1007/s00044-013-0671-8

  日期：2014.2

  Ultrasound promoted, cerium ammonium nitrate catalyzed sustainable synthesis of spiro[indoline3,4'-pyrano[2,3-c]pyrazole] derivatives (4a-l) is reported herein. The synthesized compounds were screened for their antioxidant activities as free radical scavenging effect on diphenylpicryl hydrazine (DPPH center dot), 2,2'-azino-bis(3-ethylbenzthiazoline- 6-sulphonic acid) (ABTS(center dot+)) and nitric oxide (NO) radicals. The screened compounds showed potent scavenging activities against DPPH center dot, ABTS(center dot+) and NO radicals. In order to further extend on studies and to obtain a deep insight into structure activity relationship of this class of compounds, we designed N-substitution of indole moiety with the aim to study its antioxidant potential.
• CsF promoted rapid synthesis of spirooxindole‐pyran annulated heterocycles at room temperature in ethanol
  作者：Yogesh B. Wagh、Swapnil A. Padvi、Pramod P. Mahulikar、Dipak S. Dalal

  DOI：10.1002/jhet.3846

  日期：2020.3

  straightforward synthetic strategy for the construction of functionalized spirooxindole‐pyran annulated heterocycles is described. The procedure is based on CsF‐promoted rapid tandem Knoevenagel‐Michael‐Cyclocondensation reaction of isatin, malononitrile, and 4‐hydroxycoumarin/barbituric acids/pyrazolone at room temperature in ethanol. This methodology has various advantages like easy operational, excellent

  描述了一种新型的，多功能的，直接的合成策略，用于构建功能化螺氧杂吲哚-吡喃环杂环。该程序基于室温下在乙醇中，由CsF促进的快速串联串联的Isatin，丙二腈和4-羟基香豆素/巴比妥酸/吡唑啉酮的Knoevenagel-Michael-环缩合反应。该方法具有多种优势，例如操作简便，在短反应时间内（3-25分钟）即可获得出色的收率，以及产物的简单分离。CsF兼具碱和羰基活化剂的作用。