5-[4-(二甲氨基)苯基]氨基吡嗪 | 1021186-70-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 5-[4-(二甲氨基)苯基]氨基吡嗪
• 英文名称: 5-[4-(dimethylamino)phenyl]aminopyrazine
• 英文别名: 5-[4-(Dimethylamino)phenyl]pyrazin-2-amine
• CAS: 1021186-70-8
• 化学式: C₁₂H₁₄N₄
• 分子量: 214.27
• InChiKey: MQAYOLBOCDASJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-[4-(二甲氨基)苯基]氨基吡嗪 在 盐酸 作用下， 以 1,4-二氧六环 、 二乙二醇二甲醚 、 水 为溶剂， 反应 25.0h， 生成
  参考文献：
  名称：

  Chemiluminescent 2,6-diphenylimidazo[1,2- a]pyrazin-3(7 H)-ones: a new entry to Cypridina luciferin analogues

  摘要：

  描述了一种具有取代苯基基团的2,6-二苯基咪唑[1,2-a]吡嗪-3(7H)-酮衍生物的化学发光特性研究。在衍生物1中，6-[4-(二甲氨基)苯基]衍生物（1a,d–f）在二甘醇/醋酸盐缓冲液中显示出高的量子产率（ΦCL ≥ 0.0025），这是Cypridina生物发光的模型反应条件。它们的高效化学发光主要是由C6处取代基的电子效应引起的。特别地，衍生物1a,d–f中C6的电子给体4-(二甲氨基)苯基对通过电荷转移诱导发光（CTIL）机制提高化学激发效率（ΦS）起着至关重要的作用。这些结果为设计具有高效化学发光的新型Cypridina发光素类似物提供了有用的信息。

  DOI：

  10.1039/c3pp50197c

文献信息

• Fluorescence Properties of Diphenylthiazolo[4,5-<i>b</i>]pyrazines Tuned by Donor-Acceptor Substituent Effects
  作者：Tatsuki Nakagawa、Minoru Yamaji、Shojiro Maki、Haruki Niwa、Takashi Hirano

  DOI：10.1111/php.12440

  日期：2015.7

  Fluorescence properties of 2,6‐ and 2,5‐diphenylthiazolo[4,5‐b]pyrazine (TPy) derivatives having an electron‐donating substituent (methoxy and dimethylamino) on the 6‐ and 5‐phenyl groups were studied. It was found that 2,6‐diphenyl derivatives fluoresce more efficiently than 2,5‐diphenyl derivatives. Furthermore, a 2,6‐diphenyl derivative having an additional cyano group on the 2‐phenyl ring was an

  研究了在 6- 和 5- 苯基上具有给电子取代基（甲氧基和二甲氨基）的 2,6- 和 2,5- 二苯基噻唑并[4,5-b] 吡嗪 (TPy) 衍生物的荧光性质。发现 2,6-二苯基衍生物比 2,5-二苯基衍生物更有效地发出荧光。此外，在 2-苯环上具有额外氰基的 2,6-二苯基衍生物是一种优异的荧光团，显示出广泛的溶剂致变色和高荧光产率。基于获得的光谱数据和关于取代基对荧光特性的影响的机制解释，提供了有关设计新 TPy 荧光团的有用信息。
• 5-[4-(Dimethylamino)phenyl]-2-benzamidopyrazines: fluorescent dyes based on Cypridina oxyluciferin
  作者：Takashi Hirano、Tatsuki Nakagawa、Ai Kodaka、Shojiro Maki、Haruki Niwa、Minoru Yamaji

  DOI：10.1007/s11164-012-0645-3

  日期：2013.1

  To clarify the acyl substitution effect on the fluorescent property of Cypridina oxyluciferin analogs, which have the 4-(dimethylamino)phenyl group at C5, we compared the spectroscopic properties of benzamide 1b and its 2,6-dimethylphenyl derivative 1c in various solvents with those of acetamide 1a. Similarity of the fluorescence wavelengths of 1a–c indicates that the π-electronic conjugation in the excited singlet (S1) state is terminated at the acyl group and that the benzamide moiety in 1b has little effect on modulating the florescence color. The similar fluorescence solvatochromism of 1a–c reveals that their S1 states have a similar intramolecular charge transfer character. The fact that 1a–c have various fluorescence quantum yields and lifetimes depending on solvent polarity and hydrogen bonding interactions in solutions provides information about the decay processes competing with the fluorescence process in the S1 states. Among 1a–c, benzamide 1b exhibits the most sensitive variation of the fluorescence intensity depending on the solvent used. Similarity of the fluorescence spectra of 1a–c adsorbed in NaY zeolites was also observed, which indicates that the S1 states of 1a–c give mobile conformers in the NaY supercages. The relationship between the molecular structures of 1a–c and their spectroscopic properties will provide a guide for designing a new fluorophore based on Cypridina oxyluciferin.

  为了弄清酰基取代对 Cypridina 氧荧光素类似物荧光特性的影响，我们比较了苯甲酰胺 1b 及其 2,6-二甲基苯基衍生物 1c 与乙酰胺 1a 在不同溶剂中的光谱特性。1a-c 的荧光波长相似，表明激发态单线态（S1）的π-电子共轭终止于酰基，1b 中的苯甲酰胺分子对荧光颜色的调节作用很小。1a-c 类似的荧光溶解色度表明，它们的 S1 态具有类似的分子内电荷转移特性。根据溶液中溶剂极性和氢键相互作用的不同，1a-c 具有不同的荧光量子产率和寿命，这一事实提供了有关与 S1 态荧光过程竞争的衰变过程的信息。在 1a-c 中，苯甲酰胺 1b 的荧光强度随所用溶剂的变化最为敏感。在 NaY 沸石中吸附的 1a-c 的荧光光谱也具有相似性，这表明 1a-c 的 S1 态在 NaY 超级包裹体中具有可移动的构象。1a-c 的分子结构与其光谱特性之间的关系将为设计基于 Cypridina oxyluciferin 的新型荧光团提供指导。
• Spectroscopic properties of BF2 complexes of N-(5-phenyl-2-pyrazinyl)pivalamides exhibiting fluorescence in solution and solid state
  作者：Sojiro Hachiya、Daisuke Hashizume、Hiroshi Ikeda、Minoru Yamaji、Shojiro Maki、Haruki Niwa、Takashi Hirano

  DOI：10.1016/j.jphotochem.2015.10.014

  日期：2016.12

  Boron difluoride (BF2) complexes of N-(5-phenyl-2-pyrazinyl)pivalamide and its derivatives having a substituent on the phenyl group were prepared and theirspectroscopic properties were investigated. It was found that the BF2 complexes show fluorescence in solution and the solid state. The origins of the fluorescence properties are discussed on the basis of the fluorescence yields and lifetimes, crystal structures and DFT calculations. The present work would provide a guide to design BF2 complexes of amidopyrazines exhibiting solid state fluorescence. (C) 2015 Elsevier B.V. All rights reserved.
• Chemiluminescent 2,6-diphenylimidazo[1,2- a]pyrazin-3(7 H)-ones: a new entry to Cypridina luciferin analogues
  作者：Yuki Ishii、Chihiro Hayashi、Yoshihisa Suzuki、Takashi Hirano

  DOI：10.1039/c3pp50197c

  日期：2014.2

  An investigation of the chemiluminescent properties of 2,6-diphenylimidazo[1,2- a]pyrazin-3(7 H)-one derivatives (1), having substituted phenyl groups, is described. Among the derivatives 1, the 6-[4-(dimethylamino)phenyl] derivatives (1a,d–f) gave a high quantum yield (ΦCL ≥ 0.0025) in diglyme/acetate buffer, which is a model reaction condition for the Cypridina bioluminescence. Their efficient chemiluminescence is mainly caused by the electronic effect of the substituent at C6. In particular, the electron-donating 4-(dimethylamino)phenyl group at C6 of 1a,d–f plays an essential role in increasing the chemiexcitation efficiency (ΦS) by the charge transfer-induced luminescence (CTIL) mechanism. The results provide useful information for designing new Cypridina luciferin analogues showing efficient chemiluminescence.

  描述了一种具有取代苯基基团的2,6-二苯基咪唑[1,2-a]吡嗪-3(7H)-酮衍生物的化学发光特性研究。在衍生物1中，6-[4-(二甲氨基)苯基]衍生物（1a,d–f）在二甘醇/醋酸盐缓冲液中显示出高的量子产率（ΦCL ≥ 0.0025），这是Cypridina生物发光的模型反应条件。它们的高效化学发光主要是由C6处取代基的电子效应引起的。特别地，衍生物1a,d–f中C6的电子给体4-(二甲氨基)苯基对通过电荷转移诱导发光（CTIL）机制提高化学激发效率（ΦS）起着至关重要的作用。这些结果为设计具有高效化学发光的新型Cypridina发光素类似物提供了有用的信息。