10-(dicyanomethylene)benzanthrone | 120086-28-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 10-(dicyanomethylene)benzanthrone
• 英文别名: 2-(12-oxobenzo[a]anthracen-7-ylidene)propanedinitrile
• CAS: 120086-28-4
• 化学式: C₂₁H₁₀N₂O
• 分子量: 306.323
• InChiKey: MRUZCHLMBDIDJR-UHFFFAOYSA-N

物化性质

• 熔点：
  237-238 °C(Solv: acetonitrile (75-05-8))
• 沸点：
  535.2±38.0 °C(Predicted)
• 密度：
  1.359±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 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

上下游信息

反应信息

• 作为反应物：
  描述：

  二(三甲基硅基)碳酰二亚胺 、 10-(dicyanomethylene)benzanthrone 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Synthesis, electrochemistry, and crystal structure of N,N'-dicyanoquinonediimine (DCNQI) derivatives containing fused benzene rings

  摘要：

  A series of novel fused aromatic N,N'-dicyanoquinonediimines (DCNQI) derivatives (3, 5, 7, and 9) and N-cyanoquinonemonoimines (4, 6, 8, and 10) has been synthesized by reaction of the corresponding quinones with bis(trimethylsilyl)carbodiimide (BTC). The acceptor ability is discussed in terms of both steric and electronic effects. Cyclic voltammetric data reveal two one-electron reduction waves of the corresponding radical-anion and dianion of each compound. The first reduction potentials are more negative than those of the more simple DCNQI (2a) and TMDCNQI (2b) acceptors. In contrast, the novel hybrid acceptor molecule 13 shows a single two-electron wave which corresponds to the dianion. The X-ray analysis of acceptor 13 allows one to compare, for the first time, the structural effect of the dicyanomethylene and N-cyanimine groups on the same molecule.

  DOI：

  10.1021/jo00047a028
• 作为产物：
  描述：

  苯并蒽-7,12-二酮 、 丙二腈 在 吡啶 、 四氯化钛 作用下， 以 氯仿 为溶剂， 反应 3.0h， 以42%的产率得到10-(dicyanomethylene)benzanthrone
  参考文献：
  名称：

  Syntheses and electrochemical properties of tetracyano-p-quinodimethane derivatives containing fused aromatic rings

  摘要：

  DOI：

  10.1021/jo00272a020

文献信息

• Syntheses and electrochemical properties of tetracyano-p-quinodimethane derivatives containing fused aromatic rings
  作者：Nazario Martin、Richard Behnisch、Michael Hanack

  DOI：10.1021/jo00272a020

  日期：1989.5
• MARTIN, NAZARIO;BEHNISCH, RICHARD;HANACK, MICHAEL, J. ORG. CHEM., 54,(1989) N1, C. 2563-2568
  作者：MARTIN, NAZARIO、BEHNISCH, RICHARD、HANACK, MICHAEL

  DOI：——

  日期：——
• Synthesis, electrochemistry, and crystal structure of N,N'-dicyanoquinonediimine (DCNQI) derivatives containing fused benzene rings
  作者：Nazario Martin、Juan A. Navarro、Carlos Seoane、Armando Albert、Felix H. Cano、James Y. Becker、Vladimir Khodorkovsky、Eli Harlev、Michael Hanack

  DOI：10.1021/jo00047a028

  日期：1992.10

  A series of novel fused aromatic N,N'-dicyanoquinonediimines (DCNQI) derivatives (3, 5, 7, and 9) and N-cyanoquinonemonoimines (4, 6, 8, and 10) has been synthesized by reaction of the corresponding quinones with bis(trimethylsilyl)carbodiimide (BTC). The acceptor ability is discussed in terms of both steric and electronic effects. Cyclic voltammetric data reveal two one-electron reduction waves of the corresponding radical-anion and dianion of each compound. The first reduction potentials are more negative than those of the more simple DCNQI (2a) and TMDCNQI (2b) acceptors. In contrast, the novel hybrid acceptor molecule 13 shows a single two-electron wave which corresponds to the dianion. The X-ray analysis of acceptor 13 allows one to compare, for the first time, the structural effect of the dicyanomethylene and N-cyanimine groups on the same molecule.