5,6-Bis(benzylsulfanyl)pyrazine-2,3-dicarbonitrile | 185827-54-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 5,6-Bis(benzylsulfanyl)pyrazine-2,3-dicarbonitrile
• CAS: 185827-54-7
• 化学式: C₂₀H₁₄N₄S₂
• 分子量: 374.49
• InChiKey: QYCYMGRWXWAOLX-UHFFFAOYSA-N

物化性质

• 沸点：
  574.9±50.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5,6-Bis(benzylsulfanyl)pyrazine-2,3-dicarbonitrile 在 magnesium n-propoxide 作用下， 以 1,4-二氧六环 、 丙醇 为溶剂， 反应 18.0h， 以61%的产率得到{29H,31H-[2,3,9,10,16,17,23,24-octakis(benzylsulfanyl)-1,4,8,11,15,18,22,25-(octaza)phthalocyaninato](2-)-N²⁹,N³⁰,N³¹,N³²}magnesium
  参考文献：
  名称：

  Preparation of Magnesium Azaphthalocyanines by Cyclotetramerisation of S-Substituted 4,5-Disulfanylpyrazine-2,3-dicarbonitriles.

  摘要：

  Four novel S-substituted 4,5-disulfanylpyrazine-2,3-dicarbonitriles have been obtained in a multistep synthesis from diaminomaleonitrile. Two of these dicarbonitriles, with ethyl or benzyl S-substituents, give pure magnesium azaphthalocyanines in good yields when reacted with magnesium propoxide in propanol and dioxane. Aromatic S-substituents are less stable during the reaction conditions used for cyclisations, and product mixtures are obtained.

  DOI：

  10.3891/acta.chem.scand.50-1153
• 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 作用下， 以 吡啶 、 丙酮 为溶剂， 反应 4.5h， 生成 5,6-Bis(benzylsulfanyl)pyrazine-2,3-dicarbonitrile
  参考文献：
  名称：

  Preparation of Magnesium Azaphthalocyanines by Cyclotetramerisation of S-Substituted 4,5-Disulfanylpyrazine-2,3-dicarbonitriles.

  摘要：

  Four novel S-substituted 4,5-disulfanylpyrazine-2,3-dicarbonitriles have been obtained in a multistep synthesis from diaminomaleonitrile. Two of these dicarbonitriles, with ethyl or benzyl S-substituents, give pure magnesium azaphthalocyanines in good yields when reacted with magnesium propoxide in propanol and dioxane. Aromatic S-substituents are less stable during the reaction conditions used for cyclisations, and product mixtures are obtained.

  DOI：

  10.3891/acta.chem.scand.50-1153

文献信息

• Organometallic dithiolene complexes of benzenedithiolate analogues with π-coordinating and π-interacting Cp* ligand
  作者：Mitsushiro Nomura、Eriko Tsukano、Chikako Fujita-Takayama、Toru Sugiyama、Masatsugu Kajitani

  DOI：10.1016/j.jorganchem.2009.05.022

  日期：2009.9

  Organometallic dithiolene complexes, which were formulated as [Cp*M(dcbdt)] and [Cp*M(dcdmp)] (M = Co, Rh, Ir; Cp* = eta(5)-pentamethylcyclopentadienyl, dcbdt = 4,5-dicyanobenzene-1,2-dithiolate, dcdmp = 2,3-dicyano-5,6-dimercaptopyrazine) were prepared from a low valent Cp*Co-I or high valent Cp*M-III species (M-III = Co-III, Rh-III, Ir-III). The UV-Vis absorption spectral and electrochemical data of them were obtained. The lowest absorption (HOMO-LUMO) energies of them became redshift in order of the Co > Rh > Ir complexes. The reduction potentials suggested that the central metal modifies their LUMO levels. The molecular and crystal structures of [Cp*Co(dcbdt)] (3a), [Cp*Co(dcdmp)] (4a) and [Cp*Rh(dcdmp)] (4b) were determined by X-ray diffraction studies. The cobalt complexes 3a and 4a were monomeric, formally 16-electron complexes and have two-legged piano-stool geometries. The crystal structure of 3a indicated some plane-to-plane intermolecular interactions such as benzene center dot center dot center dot benzene interaction on the dcbdt ligand and two Cp*center dot center dot center dot benzene pi-pi stackings. 4a showed plane-to-plane interaction with a pseudo-4-fold-symmetry arrangement between the pyrazine moieties on the dcdmp ligand. The rhodium complex 4b was dimeric in the crystal to form a criss-cross arrangement and had a three-legged piano-stool geometry, but it was monomerized in solution. The dimer of 3b was observed in the oxidation process of the cyclic voltammogram. (C) 2009 Elsevier B.V. All rights reserved.
• CYCLIC DINITRILE COMPOUNDS AS ADDITIVES FOR ELECTROLYTE
  申请人：BASF SE

  公开号：EP3335265B1

  公开（公告）日：2020-02-26
• Preparation of Magnesium Azaphthalocyanines by Cyclotetramerisation of S-Substituted 4,5-Disulfanylpyrazine-2,3-dicarbonitriles.
  作者：Eva H. Mørkved、Lars T. Holmaas、Helge Kjøsen、Georg Hvistendahl、Markku Leskelä、Mika Polamo、Muhammed Nour Homsi、Frank K. H. Kuske、Monika Haugg、Nathalie Trabesinger-Rüf、Elmar G. Weinhold

  DOI：10.3891/acta.chem.scand.50-1153

  日期：——

  Four novel S-substituted 4,5-disulfanylpyrazine-2,3-dicarbonitriles have been obtained in a multistep synthesis from diaminomaleonitrile. Two of these dicarbonitriles, with ethyl or benzyl S-substituents, give pure magnesium azaphthalocyanines in good yields when reacted with magnesium propoxide in propanol and dioxane. Aromatic S-substituents are less stable during the reaction conditions used for cyclisations, and product mixtures are obtained.