5,6-di-(thien-2-yl)pyrazine-2,3-dicarbonitrile | 219581-08-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5,6-di-(thien-2-yl)pyrazine-2,3-dicarbonitrile
• 英文别名: 5,6-di(thiophen-2-yl)pyrazine-2,3-dicarbonitrile；2,3-dicyano-5,6-di(2-thienyl)pyrazine；[(CN)2Th2Pyz]；5,6-Dithiophen-2-ylpyrazine-2,3-dicarbonitrile；5,6-dithiophen-2-ylpyrazine-2,3-dicarbonitrile
• CAS: 219581-08-5
• 化学式: C₁₄H₆N₄S₂
• 分子量: 294.36
• InChiKey: SBSDMXFWMLBKPS-UHFFFAOYSA-N

物化性质

• 沸点：
  453.8±45.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  130
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5,6-di-(thien-2-yl)pyrazine-2,3-dicarbonitrile 在 magnesium isopropoxide 作用下， 以 丙醇 为溶剂， 反应 8.0h， 以85%的产率得到{29H,31H-[2,3,9,10,16,17,23,24-octakis(thien-2-yl)-1,4,8,11,15,18,22,25-(octaaza)phthalocyaninato](2-)-N²⁹,N³⁰,N³¹,N³²}magnesium
  参考文献：
  名称：

  Morkved, Eva H.; Ossletten, Hege; Kjosen, Helge, Journal fur Praktische Chemie (Weinheim), 2000, vol. 342, # 1, p. 83 - 86

  摘要：

  DOI：
• 作为产物：
  描述：

  2-羟基-1,2-二(2-噻吩基)乙烷-1-酮 在 三乙胺 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 40.0h， 生成 5,6-di-(thien-2-yl)pyrazine-2,3-dicarbonitrile
  参考文献：
  名称：

  Morkved, Eva H.; Ossletten, Hege; Kjosen, Helge, Journal fur Praktische Chemie (Weinheim), 2000, vol. 342, # 1, p. 83 - 86

  摘要：

  DOI：
• 作为试剂：
  描述：

  苯乙烯 、 S-(2,6-dimethylphenyl)-N-(4-methoxyphenyl)benzene sulfamine 在 5,6-di-(thien-2-yl)pyrazine-2,3-dicarbonitrile 作用下， 以 二氯甲烷 为溶剂， 以54 %的产率得到N-(2-((2,6-dimethylphenyl)thio)-1-phenylethyl)-4-methoxyaniline
  参考文献：
  名称：

  一种可见光催化制备β-氨基硫化物的方法

  摘要：

  本发明公开一种可见光催化制备β‑氨基硫化物的方法，属于有机合成技术领域。在保护气氛下，式I所示的硫胺类化合物和末端烯烃II在甲苯或者二氯甲烷有机溶剂中，以TDPZ作为可见光催化剂，在可见光照射下于25℃反应完全，分离纯化得到式III所示的β‑氨基硫化物，#imgabs0#，本发明反应原子经济性高；底物范围广泛且不受取代基电性限制；使用无金属的TDPZ光催化剂，催化剂用量少，反应条件温和，快速高效，产率高，区域选择性高，绿色环保。

  公开号：

  CN117843537A

文献信息

• Structural elaboration of dicyanopyrazine: towards push–pull molecules with tailored photoredox activity
  作者：Zuzana Hloušková、Milan Klikar、Oldřich Pytela、Numan Almonasy、Aleš Růžička、Veronika Jandová、Filip Bureš

  DOI：10.1039/c9ra04731j

  日期：——

  provided a series of catalysts based on a pyrazine heterocyclic scaffold with easy synthesis and further modification, diverse photoredox characteristics and wide application potential across modern photoredox transformations. The photoredox catalytic activities of the target catalysts were examined in a benchmark cross-dehydrogenative coupling and novel and challenging annulation reactions.

  作为成功的二氰基吡嗪光氧化还原催化剂的延伸，设计并轻松合成了一系列具有系统改变结构的X形推挽分子；它们的结构-性质关系通过以下方式详细阐明实验和理论计算。双氰基吡嗪被证明是一种强大的光氧化还原催化剂，具有推挽式排列，可以通过互换 D-π-A 系统的特定部分来轻松调整性能。改变氰基受体与甲氧基、甲硫基和噻吩基供体的相互位置以及修饰连接基可以广泛调整催化剂的基本性质。与目前可用的有机光氧化还原催化剂相反，我们提供了一系列基于吡嗪杂环支架的催化剂，具有易于合成和进一步改性、多种光氧化还原特性和在现代光氧化还原转化中的广泛应用潜力。
• Dicyanopyrazine-derived push–pull chromophores for highly efficient photoredox catalysis
  作者：Yu Zhao、Chenhao Zhang、Kek Foo Chin、Oldřich Pytela、Guo Wei、Hongjun Liu、Filip Bureš、Zhiyong Jiang

  DOI：10.1039/c4ra05525j

  日期：——

  Here, we report dicyanopyrazine (DPZ)-derived push–pull chromophores, easily prepared and tunable organic compounds, as new kinds of photoredox catalysts.

  在这里，我们报告了以二氰基吡嗪（DPZ）为基础的推-拉式色团，作为新型的光氧化还原催化剂，这些有机化合物易于制备并可调控。
• Tetra-2,3-pyrazinoporphyrazines with Externally Appended Thienyl Rings: Synthesis, UV–Visible Spectra, Electrochemical Behavior, and Photoactivity for the Generation of Singlet Oxygen
  作者：Giorgia De Mori、Zhen Fu、Elisa Viola、Xiaohui Cai、Claudio Ercolani、Maria Pia Donzello、Karl M. Kadish

  DOI：10.1021/ic2007556

  日期：2011.9.5

  examined octathienyl compounds [Th8TPyzPzM] behave as electron-deficient macrocycles, and UV–visible spectral measurements provide useful information about how the peripheral thienyl rings influence the electronic distribution over the entire macrocyclic framework. Cyclic voltammetric and spectroelectrochemical data confirm the easier reducibility of the compounds as compared to the related phthalocyanine

  一系列带有在外部附着的2-噻吩基环的吡嗪并卟啉大环，表示为[Th 8 TPyzPzM]，其中Th 8 TPyzPz =四（2,3- [5,6-二（2-噻吩基）吡嗪并基]制备了Mg II（H 2 O），Zn II，Co II，Cu II或2H 1，并分离为固体空气稳定的水合物质。所有这些化合物完全不溶于水，其特征在于它们的紫外可见光谱和在二甲基甲酰胺（DMF），二甲基亚砜和吡啶溶液中的电化学行为。分子聚集发生在浓度约。10 –4M，但单体在10 –5 M或更小的稀溶液中形成。检查的八环烯基化合物[Th 8 TPyzPzM]表现为缺乏电子的大环，紫外可见光谱测量提供了有关外围噻吩基环如何影响整个大环框架上电子分布的有用信息。循环伏安法和光谱电化学数据证实，与相关的酞菁类似物相比，该化合物更易还原，并且该化合物的四个逐步单电子还原的总体氧化还原行为和热力学势均与较早前研究的八吡啶类似物相似[ Py
• Structural Flexibility and Role of Vicinal 2-Thienyl Rings in 2,3-Dicyano-5,6-di(2-thienyl)-1,4-pyrazine, [(CN)₂Th₂Pyz], Its Palladium(II) Complex [(CN)₂Th₂Pyz(PdCl₂)₂], and the Related Pentametallic Pyrazinoporphyrazines [(PdCl₂)₄Th₈TPyzPzM] (M = Mg^II(H₂O), Zn^II)
  作者：Maria Pia Donzello、Giorgia De Mori、Elisa Viola、Claudio Ercolani、Enrico Bodo、Luisa Mannina、Donatella Capitani、Corrado Rizzoli、Lorenzo Gontrani、Giuliana Aquilanti、Karl M. Kadish、Paola D’Angelo

  DOI：10.1021/ic201678p

  日期：2011.12.5

  The solid state and solution structure of 2,3-dicyano-5,6-di(2-thienyl)-1, 4-pyrazines [(CN)(2)Th(2)Pyz], and its pd(II) derivative, [(CN)(2)Th(2)Pyz(PdCl2)2]center dot H2O, formed by reaction of [(CN)(2)Th(2)Pyz] with [(C6H5CN)(2)Pdcl(2)] were characterized by X-ray, UV-visible, H-1 and C-13 NMR, and extended X-ray absorption fine structure (EXAFS) spectral measurements. The X-ray crystal structure of [(CN)(2)Th(2)Pyz] shows the presence of one thienyl ring positioned orthogonal to the rest of the molecule, with the two vicinal thienyl rings lying orthogonal to each other in a rare arrangement. NMR studies of [(CN)(2)Th(2)Pyz] in the solid state and in solutions of dimethylformamide or dimethyl sulfoxide confirm a nonequivalence of the thienyl rings in the solid state and also in solution. EXAFS results indicate that two distinct Pd-II coordination sites are formed at the di(2-thienyl)pyrazino moiety of [(CN)(2)Th(2)Pyz(PdCl2)(2)]center dot H2O, with identical Pd-N-pyz (2.03(3) angstrom) and Pd-Cl (2.36(3) angstrom) bond lengths but with different Pd-Sl (2.25(4) angstrom) and Pd-S2 (3.21(5) angstrom) bond distances in an overall asymmetric molecular framework. Density functional theory (DFT) and time-dependent DFT (TDDFT) theoretical studies also provide information about the structure and spectral behavior of the precursor and its metalated Pd-II derivative. H-1/C-13 NMR and UV-visible spectral measurements were also carried out on two heteropentametallic porphyrazine macrocycles which were prepared by a reaction of PdCl2 with [Th(8)TPyzPzM] where Th(8)TPyzPz = tetrakis-2,345,6-di-(2-thienyl)-pyrazino]porphyrazinato dianion and M = Mg-II(H2O) or Zn-II. Spectroscopic data on the newly synthesized [(PdCl2)(4)Th(8)TPyzPzM] compounds suggest that the binding of PdCl2 involves coordination sites of the type S2(th)PdCl2 with the two thienyl rings of each di(2-thienyl)pyrazino fragment bound to Pd-II in an equivalent manner ("th-th" coordination). This is similar to what was found for the corresponding octapyridinated analogues ("py-py" coordination).