1'-Methyl-2'-oxo-1',2'-dihydrospiro[cyclopropane-1,3'-indole]-2,2,3,3-tetracarbonitrile | 889955-24-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1'-Methyl-2'-oxo-1',2'-dihydrospiro[cyclopropane-1,3'-indole]-2,2,3,3-tetracarbonitrile
• 英文别名: 1'-methyl-2'-oxospiro[cyclopropane-3,3'-indole]-1,1,2,2-tetracarbonitrile
• CAS: 889955-24-2
• 化学式: C₁₅H₇N₅O
• mdl: MFCD06617477
• 分子量: 273.253
• InChiKey: OODCPYNASUUNIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  116
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1'-Methyl-2'-oxo-1',2'-dihydrospiro[cyclopropane-1,3'-indole]-2,2,3,3-tetracarbonitrile 在 sodium methylate 、 溶剂黄146 作用下， 反应 2.0h， 生成 2-imino-1'-metyl-2',4-dioxospiro[3-azabicyclo[3.1.0]hexane-6,3'-indole]-1,5-dicarbonitrile
  参考文献：
  名称：

  Reactions of 2′-oxo-1′,2′-dihydrospiro[cyclopropane-1,3′-indole]-2,2,3,3-tetracarbonitriles with nucleophiles

  摘要：

  2'-Oxo-1',2'-dihydrospiro[cyclopropane-1,3'-indole]-2,2,3,3-tetracarbonitriles reacted with oxygen-centered nucleophiles to form addition products at the cyano groups with conservation of the three-membered ring. Reactions of the title compounds with alcohols required the presence of base catalyst, and the products, 2-amino-4,4-dialkoxy-2'-oxo-1',2'-dihydrospiro[3-azabicyclo[3.1.0]hex-2-ene-6,3'-indole]-1,5-dicarbonitriles, were converted into the corresponding 2-imino-2',4-dioxospiro[3-azabicyclo[3.1.0]hexane-6,3'-indole]-1,5-dicarbonitriles and 2,2',4-trioxospiro[3-azabicyclo[3.1.0] hexane-6,3'-indole]-1,5-dicarbonitriles by the action of acetic and sulfuric acids, respectively. The reactions with ketone oximes occurred in the absence of a catalyst, yielding 2-amino-4,4-bis(alkylideneaminooxy)-2'-oxo-1',2'-dihydrospiro[3-azabicyclo[3.1.0] hex-2-ene-6,3'-indole]-1,5-dicarbonitriles. The reactions with thiols, aliphatic amines, and anilines were accompanied by opening of the three-membered ring. In the reactions with triphenylphosphine and thiols 2-(2-oxo-2,3-dihydro-1H-indol-3-ylidene) malononitrile was obtained, while morpholine and N,N-dimethylaniline gave rise, respectively, to 3,3-diaryl- and 3,3-dimorpholino-1H-indol-2(3H)-ones and tri- and dicyanoethylene derivatives.

  DOI：

  10.1134/s1070428011030110

文献信息

• Reactions of 2′-oxo-1′,2′-dihydrospiro[cyclopropane-1,3′-indole]-2,2,3,3-tetracarbonitriles with nucleophiles
  作者：Ya. S. Kayukov、O. V. Kayukova、E. S. Kalyagina、I. N. Bardasov、O. V. Ershov、O. E. Nasakin、V. A. Tafeenko

  DOI：10.1134/s1070428011030110

  日期：2011.3

  2'-Oxo-1',2'-dihydrospiro[cyclopropane-1,3'-indole]-2,2,3,3-tetracarbonitriles reacted with oxygen-centered nucleophiles to form addition products at the cyano groups with conservation of the three-membered ring. Reactions of the title compounds with alcohols required the presence of base catalyst, and the products, 2-amino-4,4-dialkoxy-2'-oxo-1',2'-dihydrospiro[3-azabicyclo[3.1.0]hex-2-ene-6,3'-indole]-1,5-dicarbonitriles, were converted into the corresponding 2-imino-2',4-dioxospiro[3-azabicyclo[3.1.0]hexane-6,3'-indole]-1,5-dicarbonitriles and 2,2',4-trioxospiro[3-azabicyclo[3.1.0] hexane-6,3'-indole]-1,5-dicarbonitriles by the action of acetic and sulfuric acids, respectively. The reactions with ketone oximes occurred in the absence of a catalyst, yielding 2-amino-4,4-bis(alkylideneaminooxy)-2'-oxo-1',2'-dihydrospiro[3-azabicyclo[3.1.0] hex-2-ene-6,3'-indole]-1,5-dicarbonitriles. The reactions with thiols, aliphatic amines, and anilines were accompanied by opening of the three-membered ring. In the reactions with triphenylphosphine and thiols 2-(2-oxo-2,3-dihydro-1H-indol-3-ylidene) malononitrile was obtained, while morpholine and N,N-dimethylaniline gave rise, respectively, to 3,3-diaryl- and 3,3-dimorpholino-1H-indol-2(3H)-ones and tri- and dicyanoethylene derivatives.