6'-amino-1',3'-dimethyl-2-oxo-1'H,2H-spiro[acenaphthylene-1,4'-pyrano[2,3-c]pyrazole]-5'-carbonitrile | 1383174-08-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6'-amino-1',3'-dimethyl-2-oxo-1'H,2H-spiro[acenaphthylene-1,4'-pyrano[2,3-c]pyrazole]-5'-carbonitrile
• 英文别名: 6'-Amino-1',3'-dimethyl-2-oxospiro[acenaphthylene-1,4'-pyrano[2,3-c]pyrazole]-5'-carbonitrile；6'-amino-1',3'-dimethyl-2-oxospiro[acenaphthylene-1,4'-pyrano[2,3-c]pyrazole]-5'-carbonitrile
• CAS: 1383174-08-0
• 化学式: C₂₀H₁₄N₄O₂
• 分子量: 342.357
• InChiKey: NOKQUCGGGGLXIV-UHFFFAOYSA-N

物化性质

• 沸点：
  657.1±55.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  26
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  93.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,3-二甲基-5-吡唑酮 、 丙二腈 、 苊醌 以 水 为溶剂， 反应 0.25h， 以93%的产率得到6'-amino-1',3'-dimethyl-2-oxo-1'H,2H-spiro[acenaphthylene-1,4'-pyrano[2,3-c]pyrazole]-5'-carbonitrile
  参考文献：
  名称：

  General non-catalytic approach to spiroacenaphthylene heterocycles: multicomponent assembling of acenaphthenequinone, cyclic CH-acids and malononitrile

  摘要：

  The new type of non-catalytic cascade reaction was found: the direct multicomponent reaction of acenaphthenequinone, cyclic CH-acids, and malononitrile to form spiroacenaphthylene heterocycles. The direct heating in water acenaphthenequinone, cyclic CH-acids, and malononitrile at 80 degrees C results in the formation of spiroacenaphthylene heterocycles in 90-95% yields. Thus, a new simple and efficient green 'one-pot' method to synthesize substituted spiroacenaphthylene frameworks was found directly from simple starting compounds. The application of this convenient green multicomponent method is also beneficial from the viewpoint of diversity-oriented large-scale processes. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.05.005

文献信息

• Basic Ionic Liquid-Catalyzed One-Pot Synthesis of the Spiroacenaphthylene Derivatives in Water Medium
  作者：Jia Zheng、Yiqun Li

  DOI：10.1016/j.mencom.2012.05.012

  日期：2012.5

  The basic ionic liquid (benzyl)(dimethyl)(N,N-dimethylaminoethyl)ammonium chloride was found to be an efficient and reusable catalyst for the synthesis of spiroacenaphthylenes via the multicomponent reaction between acenaphthenequinone, malononitrile and alpha-methylenecarbonyl compounds (beta-diketones, pyrazolones) in water.
• General non-catalytic approach to spiroacenaphthylene heterocycles: multicomponent assembling of acenaphthenequinone, cyclic CH-acids and malononitrile
  作者：Michail N. Elinson、Alexey I. Ilovaisky、Valentina M. Merkulova、Pavel A. Belyakov、Fructuoso Barba、Belen Batanero

  DOI：10.1016/j.tet.2012.05.005

  日期：2012.7

  The new type of non-catalytic cascade reaction was found: the direct multicomponent reaction of acenaphthenequinone, cyclic CH-acids, and malononitrile to form spiroacenaphthylene heterocycles. The direct heating in water acenaphthenequinone, cyclic CH-acids, and malononitrile at 80 degrees C results in the formation of spiroacenaphthylene heterocycles in 90-95% yields. Thus, a new simple and efficient green 'one-pot' method to synthesize substituted spiroacenaphthylene frameworks was found directly from simple starting compounds. The application of this convenient green multicomponent method is also beneficial from the viewpoint of diversity-oriented large-scale processes. (C) 2012 Elsevier Ltd. All rights reserved.