2,6-diazidopyrazine | 74273-75-9

• 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: 2,6-diazidopyrazine
• CAS: 74273-75-9
• 化学式: C₄H₂N₈
• 分子量: 162.113
• InChiKey: CVARKKPQWQKVMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,6-diazidopyrazine 生成 N,N'bis-(4-Carbethoxy-1,2,3-triazole-5-yl)-2,6-diaminopyrazine
  参考文献：
  名称：

  SHAW J. T.; BROTHERTON C. E.; MOON R. W.; WINLAND M. D.; ANDERSON M. D.; +, J. HETEROCYCL. CHEM., 1980, 17, NO 1, 11-16

  摘要：

  DOI：
• 作为产物：
  描述：

  2,6-二氯吡嗪 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 生成 2,6-diazidopyrazine
  参考文献：
  名称：

  2,6-Diamino-3,5-diaryl-1,4-pyrazine Derivatives as Novel Antioxidants

  摘要：

  芳基硼酸与2,6-二胺-3,5-二溴-1,4-吡嗪（6）的耦合反应生成了2,6-二氨基-3,5-二芳基-1,4-吡嗪（7）。7与甲基乙二醛在水相乙醇-盐酸中反应，得到了N,N"-二取代产物8，而不是预期的 bicyclic 噁唑吡嗪酮1。2,6-二[1-(乙氧基羧基)-乙基氨基]-3,5-二芳基-1,4-吡嗪8是强效的AAPH诱导亚油酸过氧化的抑制剂。

  DOI：

  10.1055/s-2001-12764

文献信息

• 2,6-Diamino-3,5-diaryl-1,4-pyrazine Derivatives as Novel Antioxidants
  作者：Jean-François Cavalier、Maggi Burton、Catherine De Tollenaere、Frédérique Dussart、Cécile Marchand、Jean-François Rees、Jacqueline Marchand-Brynaert

  DOI：10.1055/s-2001-12764

  日期：——

  The coupling of arylboronic acids with 2,6-diamino-3,5-dibromo-1,4-pyrazine (6) gave 2,6-diamino-3,5-diaryl-1,4-pyrazines (7). The reaction of 7 with methyl glyoxal in aqueous EtOH-HCl led to the N,N"-disubstituted products 8, instead of the expected bicyclic imidazolopyrazinones 1. The 2,6-bis[1-(ethoxycarbonyl)-ethylamino]-3,5-diaryl-1,4-pyrazines 8 are powerful inhibitors of the AAPH-induced linoleate peroxidation.

  芳基硼酸与2,6-二胺-3,5-二溴-1,4-吡嗪（6）的耦合反应生成了2,6-二氨基-3,5-二芳基-1,4-吡嗪（7）。7与甲基乙二醛在水相乙醇-盐酸中反应，得到了N,N"-二取代产物8，而不是预期的 bicyclic 噁唑吡嗪酮1。2,6-二[1-(乙氧基羧基)-乙基氨基]-3,5-二芳基-1,4-吡嗪8是强效的AAPH诱导亚油酸过氧化的抑制剂。
• Bimodal association of a bis-1,2,3-dithiazolyl radical
  作者：Alicea A. Leitch、Courtney E. McKenzie、Richard T. Oakley、Robert W. Reed、John F. Richardson、Lenora D. Sawyer

  DOI：10.1039/b517098b

  日期：——

  The N-ethyl pyrazine-bridged bis-1,2,3-dithiazolyl radical 2 (R1 = Et) associates at room temperature as a C–C bonded σ-dimer which, on heating, converts to a laterally S–S σ-bonded structure.

  N- 乙基吡嗪键合的双-1,2,3-二噻唑基 2（R1 = Et）在室温下以 C-C 键合的σ-二聚体形式结合，加热后转变为横向的 S-S σ 键合结构。
• Shaw, John T.; Brotherton, Christine E.; Moon, Robert W., Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 11 - 16
  作者：Shaw, John T.、Brotherton, Christine E.、Moon, Robert W.、Winland, Mark D.、Anderson, Mark D.、Kyler, Keith S.

  DOI：——

  日期：——
• An Alternating π-Stacked Bisdithiazolyl Radical Conductor
  作者：Alicea A. Leitch、Robert W. Reed、Craig M. Robertson、James F. Britten、Xueyang Yu、Richard A. Secco、Richard T. Oakley

  DOI：10.1021/ja071218p

  日期：2007.6.1

  A general synthetic route to the resonance-stabilized pyrazine-bridged bisdithiazolyl framework, involving the reductive deprotection of 2,6-diaminopyrazine-bisthiocyanate and cyclization with thionyl chloride, has been developed. An N-methyl bisdithiazolyl radical, 4-methyl-4H-bis[1,2,3]dithiazolo[4,5-b:5',4'-e]pyrazin-3-yl, has been prepared and characterized in solution by electron paramagnetic resonance spectroscopy and cyclic voltammetry. Its crystal structure has been determined at several temperatures. At 295 K, the structure belongs to the space group Cmca and consists of evenly spaced radicals pi-stacked in an alternating ABABAB fashion along the x-direction. At 123 K, the space group symmetry is lowered by loss of C-centering to Pccn, so that the radicals are no longer evenly spaced along the pi-stack. At 88 K, a further lowering of space group symmetry to P2(1)/c is observed. Extended Huckel Theory band structure calculations indicate a progressive opening of a band gap at the Fermi level in the low-temperature structures. Magnetic susceptibility measurements over the range 4-300 K reveal essentially diamagnetic behavior below 120 K. Variable-temperature single-crystal conductivity (sigma) measurements indicate that the conductivity is activated, even at room temperature, with a room-temperature value sigma(RT) = 0.001 S cm(-1) and a thermal activation energy E-act = 0.19 eV. Under an applied pressure of 5 GPa, sigma(RT) is increased by 3 orders of magnitude, but the conductivity remains activated, with E-act being lowered to 0.11 eV at 5.5 GPa.
• SHAW J. T.; BROTHERTON C. E.; MOON R. W.; WINLAND M. D.; ANDERSON M. D.; +, J. HETEROCYCL. CHEM., 1980, 17, NO 1, 11-16
  作者：SHAW J. T.、 BROTHERTON C. E.、 MOON R. W.、 WINLAND M. D.、 ANDERSON M. D.、 +

  DOI：——

  日期：——