malononitril | 2446-45-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: malononitril
• 英文别名: 1,1-Dimorpholino-2,2-dicyan-ethylen；2,2-Dimorpholino-aethylen-1,1-dicarbonitril；2-(dimorpholinomethylidene)malononitrile；(di-morpholin-4-yl-methylene)-malononitrile；[Bis(morpholin-4-yl)methylidene]propanedinitrile；2-(dimorpholin-4-ylmethylidene)propanedinitrile
• CAS: 2446-45-9
• 化学式: C₁₂H₁₆N₄O₂
• 分子量: 248.285
• InChiKey: YGLMIBSSLNOPQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  72.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,4-二氯-3-环丁烯-1,2-二酮 、 malononitril 反应 3.0h， 以32%的产率得到N-(2-Chloro-3,4-dioxo-cyclobut-1-enyl)-2-cyano-3,3-di-morpholin-4-yl-acrylimidoyl chloride
  参考文献：
  名称：

  Eine einfache Synthese von Carbamimidoyl-halogeniden (Haloformamidinen) und von (dazu vinylogen) 2-Cyano-3,3-diaminopropenimidoyl-halogeniden

  摘要：

  DOI：

  10.1055/s-1980-29140
• 作为产物：
  描述：

  [双(甲硫基)亚甲基]丙烷二腈 、 吗啉 以67%的产率得到
  参考文献：
  名称：

  FUJITO HIROSHI; TOMINAGA YOSHINORI; AWAYA HIROSHI; KURATA KEIJI; MATSUDA +, YAKUGAKU DZASSI, YAKUGAKU ZASSNI, J. PHARM. SOS. JAR., 1978, 98, NO 10, 1+

  摘要：

  DOI：

文献信息

• Ried, Walter; Dietschmann, Hans, Liebigs Annalen der Chemie, 1981, # 6, p. 1009 - 1014
  作者：Ried, Walter、Dietschmann, Hans

  DOI：——

  日期：——
• Ried, Walter; Schoepke, Klaus, Liebigs Annalen der Chemie, 1986, # 2, p. 389 - 394
  作者：Ried, Walter、Schoepke, Klaus

  DOI：——

  日期：——
• 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.
• RIED, W.;SCHOEPKE, K., LIEBIGS ANN. CHEM., 1986, N 2, 389-394
  作者：RIED, W.、SCHOEPKE, K.

  DOI：——

  日期：——