2-(thiophen-3-yl)pyrazine | 56421-87-5

• 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: 2-(thiophen-3-yl)pyrazine
• 英文别名: 2-(3'-thienyl)pyrazine；2-(3-thienyl)pyrazine；2-thiophen-3-yl-pyrazine；3'-(2-Pyrazinyl)-thiophen；3-(3-Thienyal)-pyrazin；2-Thiophen-3-ylpyrazine
• CAS: 56421-87-5
• 化学式: C₈H₆N₂S
• 分子量: 162.215
• InChiKey: FUVBAGBTWBGTTQ-UHFFFAOYSA-N

物化性质

• 熔点：
  81 °C
• 沸点：
  244.8±25.0 °C(Predicted)
• 密度：
  1.241±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(thiophen-3-yl)pyrazine 在 硫酸 、 硝酸 作用下， 生成 3-(5-Nitro-3-thienyl)-pyrazin
  参考文献：
  名称：

  Bourguignon,J. et al., Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques, 1975, vol. 281, p. 1019 - 1022

  摘要：

  DOI：
• 作为产物：
  描述：

  吡嗪 、 [Thiophen-3-yl-(2,4,6-trimethoxyphenyl)-lambda3-iodanyl] trifluoromethanesulfonate 在 sodium hydroxide 作用下， 以 neat (no solvent) 为溶剂， 反应 10.0h， 以41%的产率得到2-(thiophen-3-yl)pyrazine
  参考文献：
  名称：

  Selective Aryl Radical Transfers into N-Heteroaromatics from Diaryliodonoium Salts with Trimethoxybenzene Auxiliary

  摘要：

  We have found that a series of trimethoxybenzene-based diaryl-iodonium(III) salts I (ArI+Ar'X-, where Ar = various aryl groups, Ar' = 2,4,6-trimethoxyphenyl, X- = counterion) can exclusively cause Ar-transfers during the base-induced radical couplings with N-heteroaromatic compounds 1 by working the trimethoxybenzene ring (Ar') as an inert coupling auxiliary. By the treatment with N-heteroaromatics 1 as the solvent, the metal-free arylations utilizing the specific salts I initiated by solid NaOH upon heating selectively produced the corresponding biaryls 2 in good yields without the formation of the trimethoxybenzene (Ar') coupling product.

  DOI：

  10.3987/com-16-s(s)90

文献信息

• The Highly Efficient Suzuki-Miyaura Cross-Coupling of (Hetero)aryl Chlorides and (Hetero)arylboronic Acids Catalyzed by “Bulky-yet-Flexible” Palladium-PEPPSI Complexes in Air
  作者：Jia-Sheng Ouyang、Yan-Fang Li、Fei-Dong Huang、Dong-Dong Lu、Feng-Shou Liu

  DOI：10.1002/cctc.201701076

  日期：2018.1.23

  Pd–PEPPSI complexes were designed and synthesized. The relationship between catalyst structure and properties was systematically investigated. It was revealed that “bulky‐yet‐flexible” C3 bearing ancenaphthyl backbone was a highly efficient precatalyst and could be successfully employed in Suzuki–Miyaura reactions of (hetero)aryl chlorides with (hetero)arylboronic acids at a low palladium loading in the presence

  设计并合成了一系列Pd-PEPPSI复合物。系统地研究了催化剂结构与性能之间的关系。结果表明，具有“大而灵活”的带有C3的萘基骨架是高效的预催化剂，在存在钯的情况下，可以成功地将Suzuki-Miyaura用于（杂）芳基氯与（杂）芳基硼酸的Suzuki-Miyaura反应。空气中的弱无机碱。
• <i>N</i>-Heterocarbene Palladium Complexes with Dianisole Backbones: Synthesis, Structure, and Catalysis
  作者：Dong-Hui Li、Xu-Xian He、Chang Xu、Fei-Dong Huang、Ning Liu、Dong-Sheng Shen、Feng-Shou Liu

  DOI：10.1021/acs.organomet.9b00230

  日期：2019.6.24

  C1–C5, bearing dianisole backbones and substituted N-aryl moieties have been synthesized and characterized. The electronic effect as well as the steric environment of the NHC ligands has been assessed. The synthesized palladium complexes were applied for Suzuki–Miyaura cross-coupling reactions under aerobic conditions. The relationship between the catalytic structure and catalytic performance was then

  已合成并表征了一系列钯N-杂环卡宾（NHC），配合物C1 - C5，带有二苯甲醚骨架和取代的N-芳基部分。已经评估了NHC配体的电子效应以及空间环境。合成的钯配合物用于有氧条件下的Suzuki-Miyaura交叉偶联反应。然后广泛研究了催化结构和催化性能之间的关系。通过优化反应条件，发现C4在钯含量为0.1 mol％的情况下催化（杂）芳基氯化物与（杂）芳基硼酸的交叉偶联反应非常高效。
• Palladium-Catalyzed Suzuki−Miyaura Cross-Coupling Reactions of Potassium Aryl- and Heteroaryltrifluoroborates
  作者：Gary A. Molander、Betina Biolatto

  DOI：10.1021/jo0342368

  日期：2003.5.1

  heteroaryltrifluoroborates in Suzuki-Miyaura cross-coupling reactions is presented. The coupling of aryl- and electron-rich heteroaryltrifluoroborates with aryl and activated heteroaryl bromides proceeds readily under ligandless conditions. When deactivated aryl- and heteroaryltrifluoroborates are coupled with aryl and heteroaryl bromides and chlorides, a low loading (0.5-2%) of PdCl(2)(dppf).CH(2)Cl(2) efficiently

  提出了对Suzuki-Miyaura交叉偶联反应中芳基三氟硼酸钾和杂芳基三氟硼酸钾的反应性的扩展研究。富芳基和电子富集的杂芳基三氟硼酸酯与芳基和活化的杂芳基溴化物的偶联在无配体条件下容易进行。当钝化的芳基和杂芳基三氟硼酸酯与芳基和杂芳基溴化物和氯化物偶联时，PdCl（2）（dppf）.CH（2）Cl（2）的低负载量（0.5-2％）有效催化反应。在任何一种条件下，反应通常可以在露天气氛中进行。
• Potassium <i>t</i>-Butoxide Alone Can Promote the Biaryl Coupling of Electron-Deficient Nitrogen Heterocycles and Haloarenes
  作者：Shuichi Yanagisawa、Kirika Ueda、Tadashi Taniguchi、Kenichiro Itami

  DOI：10.1021/ol8019764

  日期：2008.10.16

  The biaryl coupling of electron-deficient nitrogen heterocycles and haloarenes can be promoted by potassium t-butoxide alone, without the addition of any exogenous transition metal species. Electron-deficient nitrogen heterocycles such as pyridine, pyridazine, pyrimidine, pyrazine, and quinoxaline are arylated with haloarenes. Control experiments support a radical-based mechanism. Taking these findings

  缺电子的氮杂环和卤代芳烃的联芳基偶合可以通过单独的叔丁醇钾来促进，而无需添加任何外源过渡金属物质。电子不足的氮杂环（例如吡啶，哒嗪，嘧啶，吡嗪和喹喔啉）被卤代芳烃芳基化。对照实验支持基于根本的机制。考虑到这些发现，在高温或微波辐射下，使用叔丁醇盐碱和卤代芳烃的自由基过渡过程可能部分参与了报道的过渡金属催化的芳基化反应。
• Herbicidal thiophenesulfonamides and pyridinesulfonamides
  申请人：E.I. DU PONT DE NEMOURS AND COMPANY

  公开号：EP0165753A2

  公开（公告）日：1985-12-27

  Sulfonylurea derivatives of formula wherein B is a substituted thienyl or pyridyl group; W is O or S; R is H or CH3; and A is a mono- or bicyclic heterocyclic group, e.g. pyrimidinyl or triazinyl; and their agriculturally suitable salts, exhibit potent herbicidal activity. Some also show a plant growth regulant effect. The novel compounds may be formulated into compositions for agricultural use in conventional manner. They may be made by a variety of synthetic routes, e.g. by reacting an appropriate sulfonyl isocyanate or isothiocyanate of formula BNCW with an appropriate heterocyclic amine HNR.A.

  式中 B 是取代的噻吩基或吡啶基；W 是 O 或 S；R 是 H 或 CH3；A 是单环或双环杂环基团，如嘧啶基或三嗪基；以及它们的农用适 宜盐的磺酰脲衍生物具有强效除草活性，有些还显示出植物生长调节剂的作用。 这些新型化合物可按常规方法配制成农用组合物。 它们可通过多种合成路线制得，如将式 BNCW 的适当磺酰基异氰酸酯或异硫氰酸酯与适当的杂环胺 HNR.A 反应。