2,3-dicyano-5-(3-thienyl)-1-ethylpyrazinium tetrafluoroborate | 1104640-53-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-dicyano-5-(3-thienyl)-1-ethylpyrazinium tetrafluoroborate
• 英文别名: 1-ethyl-5-thiophen-3-ylpyrazin-1-ium-2,3-dicarbonitrile;tetrafluoroborate
• CAS: 1104640-53-0
• 化学式: BF₄*C₁₂H₉N₄S
• 分子量: 328.101
• InChiKey: GGQXZRXHWUBROK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.16
• 重原子数：
  22
• 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：
  92.6
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2,3-dicyano-5-(3-thienyl)-1-ethylpyrazinium tetrafluoroborate 在 三乙基硅烷 作用下， 以 乙腈 为溶剂， 反应 96.0h， 以82%的产率得到1-ethyl-5-thiophen-3-yl-1,4,5,6-tetrahydropyrazine-2,3-dicarbonitrile
  参考文献：
  名称：

  一些新的1-乙基-5-（杂）芳基-6-苯乙烯基-1,6-二氢吡嗪-2,3-二腈的合成，抗分枝杆菌和抗真菌评价

  摘要：

  1-烷基-2,3-二氰基-5-芳基吡嗪鎓盐的6-羟基加合物与反式-苯乙烯基硼酸的Petasis反应在室温下顺利进行，得到了相应的5-（杂）芳基-6-苯乙烯基取代基1,6-二氢吡嗪衍生物。还发现C（6）未取代的1，6-二氢-或1,4,5,6-四氢吡嗪衍生物可以容易地由相应的吡嗪鎓盐通过用三乙基硅烷还原而以高收率制备。体外筛选了所有合成的化合物对七种病原真菌菌株的抗真菌活性以及对结核分枝杆菌H 37 Rv，鸟，土壤的抗分枝杆菌活性。 以及从乌拉尔地区（俄罗斯）的结核病患者中分离出的多药耐药菌株。

  DOI：

  10.1016/j.bmcl.2014.12.025
• 作为产物：
  描述：

  2,3-dicyano-5-(thiophen-3-yl)pyrazine 、 triethyloxonium fluoroborate 以 氯仿 为溶剂， 反应 48.0h， 以72%的产率得到2,3-dicyano-5-(3-thienyl)-1-ethylpyrazinium tetrafluoroborate
  参考文献：
  名称：

  10.1007/s11178-008-2019-2

  摘要：

  DOI：

  10.1007/s11178-008-2019-2

文献信息

• Reactions of pyrazinium salts with phenols:from σH-adducts to SN Hproducts and transformations into benzo[b]furans
  作者：E. V. Verbitskiy、Yu. A. Kvashnin、P. A. Slepukhin、A. V. Kuchin、G. L. Rusinov、O. N. Chupakhin、V. N. Charushina

  DOI：10.1007/s11172-011-0144-5

  日期：2011.5

  The reaction of 5-(het)aryl-2,3-dicyano-1-ethylpyrazinium salts with phenol derivatives affords relatively stable dihydropyrazines, whereas the reactions of 6-(het)aryl-1,2,5-oxadiazolo[3,4-b]pyrazin-4-ium protic salts, depending on the phenol structure, result in products of nucleophilic substitution of hydrogen or open-chain transformation products: benzo[b]furan-substituted derivatives. The crystallographic data on the spatial structure of all types of the synthesized products were obtained.

  5-(杂)芳基-2,3-二氰基-1-乙基吡嗪盐与酚衍生物的反应生成相对稳定的二氢吡嗪，而6-(杂)芳基-1,2,5-氧代二唑[3,4-b]吡嗪-4-阳离子质子盐的反应则根据酚的结构，产生氢的亲核取代产物或开链转化产物：苯并[b]呋喃取代衍生物。获得了所合成产品所有类型的空间结构的结晶学数据。
• Synthesis, crystal structures, and properties of 5-(het)aryl-3-cyano-1-ethyl-2(1H)-pyrazinones
  作者：E. V. Verbitskiy、M. V. Berezin、P. A. Slepukhin、O. N. Zabelina、G. L. Rusinov、V. N. Charushin

  DOI：10.1007/s11172-011-0142-7

  日期：2011.5

  A simple method for the synthesis of 5-(het)aryl-3-cyano-1-ethyl-2(1H)-pyrazinones was proposed. The method is based on the hydrolysis of the corresponding 2,3-dicyanopyrazinium salts. The spectral properties of pyrazinones were studied and their crystallographic investigation was carried out. The possibility of introduction of 5-(het)aryl-3-cyano-1-ethyl-2(1H)-pyrazinones into the [2+4] cycloaddition

  提出了一种合成 5-(het)aryl-3-cyano-1-ethyl-2(1H)-pyrazinones 的简单方法。该方法基于相应的 2,3-二氰基吡嗪盐的水解。研究了吡嗪酮的光谱性质并对其进行了晶体学研究。显示了在微波活化条件下将 5-(het)aryl-3-cyano-1-ethyl-2(1H)-pyrazinones 引入 [2+4] 环加成的可能性。
• σH-Adducts of N-alkylpyrazinium and quinoxalinium salts with nucleophiles. The 1H and 13C NMR spectra and the crystal structures of P-adducts
  作者：E. V. Verbitskiy、M. V. Berezin、P. A. Slepukhin、G. L. Rusinov、V. N. Charushin

  DOI：10.1007/s11172-009-0027-1

  日期：2009.1

  The previously unknown addition products of P-nucleophiles to 5-aryl- and 5-hetaryl- 2,3-dicyano-1-ethylpyrazinium salts and to 5-aryl- and 5-hetaryl-14nethylquinoxalinium salts were synthesized. The three-dimensional structures of the P- σH-adducts of the 1,4-diazine series were established by X-ray diffraction.

  合成出以前未知的5-芳基和5-杂芳基-2,3-二氰基-1-乙基吡嗪鎓盐和5-芳基和5-杂芳基-14n乙基喹喔啉鎓盐的P-亲核体加成产物。通过X射线衍射确定了1,4-二嗪系列P-σH-加合物三维结构。
• A new approach to incorporate the carboranyl fragment into 2,5-diazabicyclo[2.2.2]oct-2-enes
  作者：Gennady L. Rusinov、Egor V. Verbitsky、Pavel A. Slepukhin、Olga N. Zabelina、Il’ya N. Ganebnykh、Valery N. Kalinin、Valentina A. Ol'shevskaya、Valery N. Charushin

  DOI：10.1016/j.mencom.2009.09.002

  日期：2009.9

  5-(Het)aryl-2,3-dicyano-1-ethylpyrazinium salts have been established to react with 9-allyl-ortho- and 9-allyl-meta-carboranes in the presence of sodium iodide into carboranylmethyl derivatives of 2,5-diazabicyclo[2.2.2]oct-2-ene.
• Reactions of Radicals Generated from 1-Ethyl-1,4-diazinium-salts: Addition to the C-C Triple Bond versus Dimerization
  作者：Gennadiy L. Rusinov、Egor V. Verbitskiy、Pavel A. Slepukhin、Olga N. Zabelina、Mikhail I. Kodess、Marina A. Ezhikova、Valeriy N. Charushin、Oleg N. Chupakhin

  DOI：10.3987/com-09-11734

  日期：——

  Radical species generated from 5-aryl-substituted 1-ethyl-2,3-dicyano-1,4-diazinium salts by action of sodium iodide undergo dimerization into [2,2']bipyrazinyl derivatives, as evidenced by NMR and X-ray crystallography data. The pyrazinyl radicals can also be involved into the addition reaction on the C-C triple bond, thus demonstrating a new synthetic route to modify the structure of pyrazines. The structures of E- and Z-isomers of 1-(1',2'-dihydropyrazinyl-2')-2-iodoethenes have been proved by H-1 and C-13 NMR spectroscopy and X-ray analysis.