5,10-bis(dicyanomethylidene)naphtho[2,3-b]pyrazine | 107041-53-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 5,10-bis(dicyanomethylidene)naphtho[2,3-b]pyrazine
• 英文别名: 2-[5-(Dicyanomethylidene)benzo[g]quinoxalin-10-ylidene]propanedinitrile
• CAS: 107041-53-2
• 化学式: C₁₈H₆N₆
• 分子量: 306.286
• InChiKey: AQJFEMYXEQUVFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  121
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1,4-Diazaanthra-9,10-quinone 、 丙二腈 在 四氯化钛 作用下， 反应 3.5h， 以13%的产率得到5,10-bis(dicyanomethylidene)naphtho[2,3-b]pyrazine
  参考文献：
  名称：

  PREPARATION AND PROPERTIES OF TETRACYANOQUINODIMETHANS FUSED WITH PYRAZINE UNITS

  摘要：

  标题化合物是由相应的醌类化合物与丙二腈在 TiCl4 催化下发生缩合反应制备的。循环伏安图数据表明，二吡嗪-TCNQ 衍生物的阴离子自由基在热力学上是稳定的。分离出了阴离子自由基盐。

  DOI：

  10.1246/cl.1986.715

文献信息

• PREPARATION AND PROPERTIES OF TETRACYANOQUINODIMETHANS FUSED WITH PYRAZINE UNITS
  作者：Yoshiro Yamashita、Takanori Suzuki、Gunzi Saito、Toshio Mukai

  DOI：10.1246/cl.1986.715

  日期：1986.5.5

  The title compounds were prepared by a TiCl4-catalyzed condensation reaction of corresponding quinones with malononitrile. The data of the cyclic voltammogram show that the anion radicals of dipyrazino-TCNQ derivatives are thermodynamically stable. The anion radical salts were isolated.

  标题化合物是由相应的醌类化合物与丙二腈在 TiCl4 催化下发生缩合反应制备的。循环伏安图数据表明，二吡嗪-TCNQ 衍生物的阴离子自由基在热力学上是稳定的。分离出了阴离子自由基盐。
• YAMASHITA YOSHIRO; SUZUKI TAKANORI; SAITO GUNZI; MUKAI TOSHIO, CHEM. LETT.,(1986) N 5, 715-718
  作者：YAMASHITA YOSHIRO、 SUZUKI TAKANORI、 SAITO GUNZI、 MUKAI TOSHIO

  DOI：——

  日期：——
• YAMASHITA YOSHIRO; SUZUKI TAKANORI; SAITO GUNZI; MUKAI TOSHIO, TECHN. REPT ISSP,(1986) N 1657, 9 PP.
  作者：YAMASHITA YOSHIRO、 SUZUKI TAKANORI、 SAITO GUNZI、 MUKAI TOSHIO

  DOI：——

  日期：——
• Pyrazino-tetracyanonaphthoquinodimethanes: sterically deformed electron acceptors affording zwitterionic radicals
  作者：Takanori Suzuki、Setsuko Miyanari、Hidetoshi Kawai、Kenshu Fujiwara、Takanori Fukushima、Tsutomu Miyashi、Yoshiro Yamashita

  DOI：10.1016/j.tet.2004.01.005

  日期：2004.2

  The X-ray analyses of the title electron acceptors (1) revealed their butterfly-shaped deformed geometry, which is not affected by the pyridyl group attached at 2-position of the pyrazino-TCNNQ skeleton. Small differences between the first and second reduction potentials (ca. 0.1 V) in pyrazino-TCNNQs show that their anion radicals (1(-.)) are prone to disproportionate into the neutral (1) and dianionic (1(2-)) species. The thermodynamically unstable anion radical species based on the pyrazino-TCNNQ skeleton could be isolated as inner salts upon electrochemical reduction of the derivatives having an N-methylpyridinium moiety at 2-position (2(+)). The zwitterionic open-shell species (2) constitute a novel class of radicals that exhibit semiconducting behavior as a single component thanks to the high electrochemical amphotericity. (C) 2004 Elsevier Ltd. All rights reserved.