2,3,5-trimethylpyrazine-N,N'-dioxide | 107486-65-7

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机氧氮鎓化合物
• 英文名称: 2,3,5-trimethylpyrazine-N,N'-dioxide
• 英文别名: 2,3,5-Trimethylpyrazine 1,4-Dioxide；2,3,5-trimethylpyrazine dioxide；2,3,5-tmpdo；2,3,5-trimethyl-4-oxidopyrazin-1-ium 1-oxide
• CAS: 107486-65-7
• 化学式: C₇H₁₀N₂O₂
• 分子量: 154.169
• InChiKey: ITGCVPGBKNVMBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  46.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cobalt(II) chloride hexahydrate 、 水 、 sodium dicyanamide 、 2,3,5-trimethylpyrazine-N,N'-dioxide 以 水 为溶剂， 以70%的产率得到[Co3(dicyanamide)6(H2O)4]*2(2,3,5-trimethylpyrazine-dioxide)
  参考文献：
  名称：

  Synthesis, Crystal Structures, and Magnetism of Cobalt Coordination Polymers Based on Dicyanamide and Pyrazine-dioxide Derivatives

  摘要：

  Three coordination polymers of Co(II) with dicyanamide (dca) were obtained by adding coligands of 2,5-dimethylpyrazine-dioxide (2,5-dmpdo), 2,3,5-trimethylpyrazine-dioxide (2,3,5-tmpdo), or 2,3,5,6-tetramethylpyrazine-dioxide (2,3,5,6-tmpdo) to the binary system of Co-dca. Co-2(dca)(4)(2,5-dmpdo)(2) (1) crystallizes in the triclinic space group P1 with a = 7.4962(2), b = 9.0364(2), c = 10.4783(4) angstrom, alpha = 72.567(1), beta = 72.557(1), gamma = 68.814(2)degrees, V = 616.61 (3) angstrom(3), Z = 1, and R1 = 0.0345. [Co-3(dca)(6)(H2O)(4)](.)2(2,3,5-tmpdo) (2) is in the monoclinic space group C2/c with a = 29.477(1), b = 7.3735(2), c = 17.4631(7) angstrom, beta = 93.652(1)degrees, V = 3787.9(2) angstrom(3), Z = 4, and R1 = 0.0532. [Co(dca)(2)(H2O)2](.)2(2,3,5,6-tmpdo) (3) is in the monoclinic space group P2(1)/c with a = 9.4739(3), b = 11.3876(3), c = 12.1778(3) angstrom, beta = 98.967(1)degrees, V = 1297.74(6) angstrom(3), Z = 4, and R1 = 0.0481. 1 contains an unusual (4, 4) Co-dca layer, representing a rare example of metal-dca coordination polymers with mixing 1,3-mu(2)- and 1,5-mu(2)-dca bridges. The Co-dca (4, 4) layers are connected by 2,5-dmpdo to give an alpha-Po-type network, which displays antiferromagnetic ordering below 10.8 K. 2 is a unique 3D framework composed of 2D twinned 1,5-mu(2)-dca bridged layers, which are connected by Co-H2O-Co linkages. The noncoordinated 2,3,5-tmpdo units and the coordination water molecules form hydrogen-bonded chains that thread the framework. 3 has alternating stacks of usual Co-dca (4, 4) layers through 1,5-mu(2)-dca bridges and organic layers of noncoordinated 2,3,5,6-tmpdo. Weak antiferromagnetic and weak ferromagnetic coupling was observed in 2 and 3, respectively.

  DOI：

  10.1021/ic048342j
• 作为产物：
  描述：

  2,3,5-三甲基吡嗪 在 Oxone 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以95.1%的产率得到2,3,5-trimethylpyrazine-N,N'-dioxide
  参考文献：
  名称：

  芳香族二嗪的氧化方法：取代的吡嗪-N-氧化物、吡嗪-N,N'-二氧化物和2,2':6',2"-三联吡啶-1,1"-二氧化物

  摘要：

  在研究氮杂芳族 TV 氧化物的分子间相互作用的过程中，有必要对吡啶和吡嗪部分进行氧化。通常，发现用 OXONE® 直接氧化可有效制备二氧化吡嗪。使用二甲基二环氧乙烷进行氧化可避免与分离特别亲水的吡嗪和吡嗪-/V-氧化物相关的问题。在这项工作中，我们描述了氧化吡嗪和吡啶部分的方便有效的合成。使用试剂 OXONE®（过氧化单硫酸钾）在水中或 OXONE® / 丙酮（二甲基二环氧乙烷）混合物中以良好的收率得到所需的 /V-氧化物产物。二甲基二环氧乙烷被证明是可溶于丙酮的化合物的一种方便的氧化剂。该程序与 Landquist 使用的非水溶液中的过氧化氢尿素或铼试剂制备喹喔啉-/V,jV'-二氧化物的方法相比，Sharpless 5a-5b 使用的铼试剂将取代的吡啶氧化成吡啶-yV-氧化物。甲基化的二氧化吡嗪 1a-g 和一氧化二氮 2a-g 通过用可商购的 OXONE® 氧化母体吡嗪来制备。产率通常良好，可与之前报道的方法相媲美（见表

  DOI：

  10.1515/hc.2001.7.4.307

文献信息

• Reaction of 2-Alkoxypropenals with α-Hydroxyamino Oximes and 1,2-Bis(hydroxyamino)cyclohexane
  作者：N. A. Keiko、E. A. Funtikova、L. I. Larina、G. I. Sarapulova、D. G. Mazhukin、T. V. Rybalova、A. Ya. Tikhonov

  DOI：10.1007/s11178-005-0361-1

  日期：2005.10

  Reactions of 2-alkoxypropenals with α-hydroxyamino oximes in neutral medium involve the aldehyde group of the former to afford both acyclic and cyclic azomethine oxides: N-(2-hydroxyiminoalkyl)-N-(2-alkoxy-2-propenylidene)amine oxides and 1-hydroxy-2,5-dihydroimidazole 3-oxides. The state of tautomeric equilibrium between the cyclic and acyclic products depends on the solvent nature and temperature. The reaction in acidic aqueous medium is accompanied by hydrolysis of the vinyl ether moiety in 2-alkoxy-propenals with formation of 2-oxopropionaldehyde which reacts with α-hydroxyamino oxime at the hydroxy-amino group to give substituted pyrazine 1,4-dioxides. The reaction of 2-alkoxypropenals with 1,2-bis-(hydroxyamino)cyclohexane leads to formation of 2-(1-alkoxyvinyl)-1,3-dihydroxyperhydrobenzimidazoles. The structure of the products was proved by IR, UV, and 1H and 13C NMR spectroscopy and X-ray analysis.

  2-烷氧丙烯醛与α-羟基氨基肟在中性介质中的反应涉及前者的醛基，生成无环和环状的亚胺氧化物：N-(2-羟基亚胺烷基)-N-(2-烷氧基-2-丙烯基)胺氧化物和1-羟基-2,5-二氢咪唑-3-氧化物。环状和无环产物之间的并置平衡状态取决于溶剂的性质和温度。在酸性水相中反应伴随着2-烷氧基丙烯醛中乙烯醚部分的水解，形成2-氧丙醛，该醛与α-羟基氨基肟在羟基氨基组上反应，生成取代的吡嗪1,4-二氧化物。2-烷氧丙烯醛与1,2-双(羟基氨基)环己烷的反应生成2-(1-烷氧基乙烯基)-1,3-二羟基全氟苯并咪唑。产品的结构通过红外光谱、紫外光谱、1H和13C核磁共振光谱以及X射线分析得到了验证。
• Reaction of 1,2-hydroxylaminooximes with 1,2-diketones. Conversion of 2-acyl-1-hydroxy-3-imidazoline 3-oxides to pyrazine 1,4-dioxides
  作者：L. N. Grigor'eva、A. Ya. Tikhonov、S. A. Amitina、L. B. Volodarskii、I. K. Korobeinicheva

  DOI：10.1007/bf00514993

  日期：1986.3
• Aromatization of 2,3-dihydro-3-hydroxypyrazine 1,4-dioxides in HSo3F-SbF5 superacid: A new pathway to pyrazine 1,4-dioxides
  作者：S. V. Morozov、L. B. Volodarskii、V. G. Shubin

  DOI：10.1007/bf00531416

  日期：1993.12
• Maeda Mikiko, Sakuma Chiseko, Kawachi Shinji, Tabei Katsumi, Kerim Abliki+, J. Labell. Compounds and Radiopharm, 36 (1995) N 1, S 85-92
  作者：Maeda Mikiko, Sakuma Chiseko, Kawachi Shinji, Tabei Katsumi, Kerim Abliki+

  DOI：——

  日期：——
• GRIGOREVA, L. N.;TIXONOV, A. YA.;AMITINA, S. A.;VOLODARSKIJ, L. B.;KOROBE+, XIMIYA GETEROTSIKL. SOEDIN., 1986, N 3, 331-338
  作者：GRIGOREVA, L. N.、TIXONOV, A. YA.、AMITINA, S. A.、VOLODARSKIJ, L. B.、KOROBE+

  DOI：——

  日期：——