2-(dicyanomethylene)-aceanthren-1-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2-(dicyanomethylene)-aceanthren-1-one
• 英文别名: 2-(2-oxoaceanthrylen-1(2H)-ylidene)malononitrile；2-(1-oxoaceanthrylen-2-ylidene)propanedinitrile
• 化学式: C₁₉H₈N₂O
• 分子量: 280.285
• InChiKey: LBTRQZNGKWXTEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(dicyanomethylene)-aceanthren-1-one 在 一水合肼 作用下， 以 苯 为溶剂， 反应 2.0h， 以43%的产率得到10-aminoaceanthryleno[1,2-c]pyridazine-9-carbonitrile
  参考文献：
  名称：

  On Condensation Reactions of Aceanthrene Quinone: Novel Heterocycles

  摘要：

  It was found that aceanthrene quinone can be condensed with ethylenediamine, 1,2-diaminobenzene, 4-nitro-1,2-diaminobenzene, 1,2-diaminoanthrene quinone, and 4,5,6-triamino-pyrimidine derivatives to give aceanthryleno[1,2-b]pyrazine and aceanthryleno [1,2-g]pteridine derivatives. Condensation of aceanthrene quinone with 2-aminoguanidine, semicarbazide, and thiosemicarbazide yielded aceanthryleno[1,2-e]triazines, condensation with 6-hydrazinopyrimidine derivatives gave 3,4-aceanthrylenopyrimido[4,5-c]pyridazines. Reaction of aceanthrene quinone with 2-cyanoethanoic acid hydrazide afforded 10,11-dihydro-10-oxo-aceanthryleno[1,2-c]pyridazine-9-carbonitrile. Treatment of aceanthrene quinone with malononitrile and hydrazine hydrate resulted in 10-aminoaceanthryleno[1,2-c]pyridazine-9-carbonitrile. The antibacterial effects of the prepared compounds were tested. Three of the compounds were tested against 60 cancer types.

  DOI：

  10.1007/s007060270008
• 作为产物：
  描述：

  1,2-苯并苊醌 、 丙二腈 在 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以92%的产率得到2-(dicyanomethylene)-aceanthren-1-one
  参考文献：
  名称：

  On Condensation Reactions of Aceanthrene Quinone: Novel Heterocycles

  摘要：

  It was found that aceanthrene quinone can be condensed with ethylenediamine, 1,2-diaminobenzene, 4-nitro-1,2-diaminobenzene, 1,2-diaminoanthrene quinone, and 4,5,6-triamino-pyrimidine derivatives to give aceanthryleno[1,2-b]pyrazine and aceanthryleno [1,2-g]pteridine derivatives. Condensation of aceanthrene quinone with 2-aminoguanidine, semicarbazide, and thiosemicarbazide yielded aceanthryleno[1,2-e]triazines, condensation with 6-hydrazinopyrimidine derivatives gave 3,4-aceanthrylenopyrimido[4,5-c]pyridazines. Reaction of aceanthrene quinone with 2-cyanoethanoic acid hydrazide afforded 10,11-dihydro-10-oxo-aceanthryleno[1,2-c]pyridazine-9-carbonitrile. Treatment of aceanthrene quinone with malononitrile and hydrazine hydrate resulted in 10-aminoaceanthryleno[1,2-c]pyridazine-9-carbonitrile. The antibacterial effects of the prepared compounds were tested. Three of the compounds were tested against 60 cancer types.

  DOI：

  10.1007/s007060270008

文献信息

• Base-mediated isocyanide-based three-component reactions: divergent synthesis of spiro-substituted furans and pyrroles
  作者：Hai-Ying Wang、Ming Bao、Bo Jiang、Liang Li

  DOI：10.1039/c5ra25408f

  日期：——

  A facile base-mediated isocyanide-based three-component cycloaddition protocol for chemoselective formation of functionalized spiro-substituted furans and pyrroles derivatives has been developed. Fairly good yields of the products, the ready availability of the starting materials and the excellent chemoselectivity are the main advantages of this method.

  已经开发了一种基于碱介导的基于异氰化物的三组分环加成方案，用于化学选择性形成官能化的螺取代的呋喃和吡咯衍生物。该方法的主要优点是产品的收率相当好，原料易得且化学选择性优异。
• On Condensation Reactions of Aceanthrene Quinone: Novel Heterocycles
  作者：Atef M. Amer、Medhat El-Mobayed、Abdel M. Ateya、Tarek S. Muhdi

  DOI：10.1007/s007060270008

  日期：2002.1

  It was found that aceanthrene quinone can be condensed with ethylenediamine, 1,2-diaminobenzene, 4-nitro-1,2-diaminobenzene, 1,2-diaminoanthrene quinone, and 4,5,6-triamino-pyrimidine derivatives to give aceanthryleno[1,2-b]pyrazine and aceanthryleno [1,2-g]pteridine derivatives. Condensation of aceanthrene quinone with 2-aminoguanidine, semicarbazide, and thiosemicarbazide yielded aceanthryleno[1,2-e]triazines, condensation with 6-hydrazinopyrimidine derivatives gave 3,4-aceanthrylenopyrimido[4,5-c]pyridazines. Reaction of aceanthrene quinone with 2-cyanoethanoic acid hydrazide afforded 10,11-dihydro-10-oxo-aceanthryleno[1,2-c]pyridazine-9-carbonitrile. Treatment of aceanthrene quinone with malononitrile and hydrazine hydrate resulted in 10-aminoaceanthryleno[1,2-c]pyridazine-9-carbonitrile. The antibacterial effects of the prepared compounds were tested. Three of the compounds were tested against 60 cancer types.