[(6-hydroxyacenaphthen-5-yl)methylidene]malononitrile | 1242056-53-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: [(6-hydroxyacenaphthen-5-yl)methylidene]malononitrile
• 英文别名: [(6-Hydroxyacenaphthen-5-yl)methylidene]-malononitrile；2-[(6-hydroxy-1,2-dihydroacenaphthylen-5-yl)methylidene]propanedinitrile
• CAS: 1242056-53-6
• 化学式: C₁₆H₁₀N₂O
• 分子量: 246.268
• InChiKey: MMJSEAONOATQST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  67.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [(6-hydroxyacenaphthen-5-yl)methylidene]malononitrile 在 三氟乙酸 作用下， 反应 1.0h， 以82%的产率得到2-oxoacenaphtho[5,6-bc]oxepine-3-carbonitrile
  参考文献：
  名称：

  peri-hydroxy acenaphthoyl compounds

  摘要：

  Reactions of peri-hydroxyacenaphthaldehyde and its O-methyl derivative with amines, aryl methyl ketones, and malononitrile gave the corresponding Schiff bases, chalcones, and arylidenemalononitrile. The latter underwent heterocyclization on heating in trifluoroacetic acid to produce 2-oxoacenaphtho[5,6-bc]-oxepine-3-carbonitrile. The condensation of 5-acetyl-6-hydroxyacenaphthene with aromatic aldehydes afforded chalcones, their mixtures with heterocyclization products, or 2-arylacenaphtho[5,6-bc]oxepin-4-one, depending on the substituent in the aromatic ring.

  DOI：

  10.1134/s1070428010030061
• 作为产物：
  描述：

  6-hydroxyacenaphthene-5-carbaldehyde 、 丙二腈 在 哌啶 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以36%的产率得到[(6-hydroxyacenaphthen-5-yl)methylidene]malononitrile
  参考文献：
  名称：

  peri-hydroxy acenaphthoyl compounds

  摘要：

  Reactions of peri-hydroxyacenaphthaldehyde and its O-methyl derivative with amines, aryl methyl ketones, and malononitrile gave the corresponding Schiff bases, chalcones, and arylidenemalononitrile. The latter underwent heterocyclization on heating in trifluoroacetic acid to produce 2-oxoacenaphtho[5,6-bc]-oxepine-3-carbonitrile. The condensation of 5-acetyl-6-hydroxyacenaphthene with aromatic aldehydes afforded chalcones, their mixtures with heterocyclization products, or 2-arylacenaphtho[5,6-bc]oxepin-4-one, depending on the substituent in the aromatic ring.

  DOI：

  10.1134/s1070428010030061