6,11-Dioxobenzo[b]oxanthrene-3-carbonitrile | 131079-95-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6,11-Dioxobenzo[b]oxanthrene-3-carbonitrile
• CAS: 131079-95-3
• 化学式: C₁₇H₇NO₄
• 分子量: 289.247
• InChiKey: RVEZSZKPOHBQEM-UHFFFAOYSA-N

物化性质

• 熔点：
  308-310.5 °C
• 沸点：
  445.6±45.0 °C(Predicted)
• 密度：
  1.55±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 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：
  76.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  二(三甲基硅基)碳酰二亚胺 、 6,11-Dioxobenzo[b]oxanthrene-3-carbonitrile 在 四氯化钛 作用下， 以 氯苯 为溶剂， 反应 24.0h， 以73%的产率得到(3-Cyano-6-cyanoiminobenzo[b]oxanthren-11-ylidene)cyanamide
  参考文献：
  名称：

  Synthesis and electrochemical properties of benzo[b]naphtho[2,3-e][1,4]-dioxin-6,11-quinones and their N,N'-dicyano quinone diimine derivatives

  摘要：

  The reaction of 2,3-dichloro-1,4-naphthoquinone (1) and catechols 2 in pyridine affords a series of substituted benzo[b]naphtho[2,3-e][1,4]dioxin-6,11-quinones 3. The latter compounds are transformed to the corresponding N,N'-dicyano quinone diimines 4, by treating them with N,N'-bis(trimethylsilyl)carbodiimide. The electrochemical studies of compounds of the type 3 and 4 in DMF and CH2Cl2, respectively, by means of cyclic voltammetry are reported. The experimental reduction potentials provide information on electron-electron repulsion in the dianionic states of 3 and 4, and hence on their potential use as acceptor components in charge-transfer complexes and organic conductors.

  DOI：

  10.1021/jo00004a042
• 作为产物：
  描述：

  2,3-二氯-1,4-萘醌 、 3,4-二羟基苯腈 在 吡啶 作用下， 反应 6.0h， 以83%的产率得到6,11-Dioxobenzo[b]oxanthrene-3-carbonitrile
  参考文献：
  名称：

  Synthesis and electrochemical properties of benzo[b]naphtho[2,3-e][1,4]-dioxin-6,11-quinones and their N,N'-dicyano quinone diimine derivatives

  摘要：

  The reaction of 2,3-dichloro-1,4-naphthoquinone (1) and catechols 2 in pyridine affords a series of substituted benzo[b]naphtho[2,3-e][1,4]dioxin-6,11-quinones 3. The latter compounds are transformed to the corresponding N,N'-dicyano quinone diimines 4, by treating them with N,N'-bis(trimethylsilyl)carbodiimide. The electrochemical studies of compounds of the type 3 and 4 in DMF and CH2Cl2, respectively, by means of cyclic voltammetry are reported. The experimental reduction potentials provide information on electron-electron repulsion in the dianionic states of 3 and 4, and hence on their potential use as acceptor components in charge-transfer complexes and organic conductors.

  DOI：

  10.1021/jo00004a042

文献信息

• CZEKANSKI, TOMASZ;HANACK, MICHAEL;BECKER, JAMES Y.;BERNSTEIN, JOEL;BITTNE+, J. ORG. CHEM., 56,(1991) N, C. 1569-1573
  作者：CZEKANSKI, TOMASZ、HANACK, MICHAEL、BECKER, JAMES Y.、BERNSTEIN, JOEL、BITTNE+

  DOI：——

  日期：——
• Synthesis and electrochemical properties of benzo[b]naphtho[2,3-e][1,4]-dioxin-6,11-quinones and their N,N'-dicyano quinone diimine derivatives
  作者：Tomasz Czekanski、Michael Hanack、James Y. Becker、Joel Bernstein、Shmuel Bittner、Leah Kaufman-Orenstein、Dina Peleg

  DOI：10.1021/jo00004a042

  日期：1991.2

  The reaction of 2,3-dichloro-1,4-naphthoquinone (1) and catechols 2 in pyridine affords a series of substituted benzo[b]naphtho[2,3-e][1,4]dioxin-6,11-quinones 3. The latter compounds are transformed to the corresponding N,N'-dicyano quinone diimines 4, by treating them with N,N'-bis(trimethylsilyl)carbodiimide. The electrochemical studies of compounds of the type 3 and 4 in DMF and CH2Cl2, respectively, by means of cyclic voltammetry are reported. The experimental reduction potentials provide information on electron-electron repulsion in the dianionic states of 3 and 4, and hence on their potential use as acceptor components in charge-transfer complexes and organic conductors.