7,8-Dimethyl-5,10-dihydropyrazino<2,3-b>chinoxalin-2,3-dicarbonitril | 116785-97-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 7,8-Dimethyl-5,10-dihydropyrazino<2,3-b>chinoxalin-2,3-dicarbonitril
• 英文别名: 7,8-dimethyl-5,10-dihydropyrazino[2,3-b]quinoxaline-2,3-dicarbonitrile
• CAS: 116785-97-8
• 化学式: C₁₄H₁₀N₆
• 分子量: 262.274
• InChiKey: RTJPUIWXKNSNEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  97.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7,8-Dimethyl-5,10-dihydropyrazino<2,3-b>chinoxalin-2,3-dicarbonitril 在 一水合肼 作用下， 反应 2.0h， 以52%的产率得到8,9-Dimethyl-6,11-dihydropyridazino<4',5':5,6>pyrazino<2,3-b>chinoxalin-1,4-diamin
  参考文献：
  名称：

  Ried, Walter; Tsiotis, Georgios, Liebigs Annalen der Chemie, 1988, p. 1197 - 1200

  摘要：

  DOI：
• 作为产物：
  描述：

  1,4,5,6-四氢-5,6-二氧-2,3-吡嗪二甲腈 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 17.0h， 生成 7,8-Dimethyl-5,10-dihydropyrazino<2,3-b>chinoxalin-2,3-dicarbonitril
  参考文献：
  名称：

  Structure–property relationships in dicyanopyrazinoquinoxalines and their hydrogen-bonding-capable dihydropyrazinoquinoxalinedione derivatives

  摘要：

  Presented here is the design, synthesis, and study of a variety of novel hydrogen-bonding-capable π-conjugated N-heteroacenes, 1,4-dihydropyrazino[2,3-b]quinoxaline-2,3-diones (DPQDs). The DPQDs were accessed from the corresponding weakly hydrogen-bonding dicyanopyrazinoquinoxaline (DCPQ) suspensions with excess potassium hydroxide, resulting in moderate to good yields. Both families of compounds were analyzed by UV–vis and NMR spectroscopy, where the consequences of hydrogen bonding capability could be assessed through the structure–property studies. Conversion of the DCPQs into hydrogen-bonding capable DPQDs results in modulation of frontier MO energies, higher molar extinction coefficients, enhanced crystallinity, and on-average higher thermal stability (where in some cases the 5% weight loss temperature is increased by up to 100 °C). Single crystal X-ray diffraction data could be obtained for three DPQDs. One reveals pairwise hydrogen bonding in the solid state as well as a herringbone packing arrangement rendering it a promising candidate for additional studies in the context of organic optoelectronic devices.

  DOI：

  10.3762/bjoc.20.92

文献信息

• Preparation, Characterization, and FET Properties of Novel Dicyanopyrazinoquinoxaline Derivatives
  作者：Jun-ichi Nishida、Naraso、Shio Murai、Eiichi Fujiwara、Hirokazu Tada、Masaaki Tomura、Yoshiro Yamashita

  DOI：10.1021/ol0494010

  日期：2004.6.1

  A series of the title dicyanopyrazinoquinoxaline derivatives have been prepared and characterized by using single-crystal X-ray structure analysis and redox potential measurements. They have strong electron-accepting properties due to the pyrazinopyrazine skeletons as well as the cyano groups. Substituents can be easily introduced at the benzene ring and control the HOMO-LUMO energy gap and the molecular packing. They show clear n-type transistor properties in the FET devices.
• RIED, WALTER;TSIOTIS, GEORGIOS, LIEBIGS ANN. CHEM.,(1988) N2, C. 1197-1199
  作者：RIED, WALTER、TSIOTIS, GEORGIOS

  DOI：——

  日期：——