6-Nitro-[1,2,5]oxadiazolo[3,4-b]pyridine 3-oxide | 127183-59-9

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 6-Nitro-[1,2,5]oxadiazolo[3,4-b]pyridine 3-oxide
• CAS: 127183-59-9
• 化学式: C₅H₂N₄O₄
• 分子量: 182.095
• InChiKey: FQCFJCXDXHFANW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.24
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  109.0
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  6-Nitro-[1,2,5]oxadiazolo[3,4-b]pyridine 3-oxide 以 丙酮 为溶剂， 生成 4-aza-6-nitrobenzofuroxan
  参考文献：
  名称：

  1H、13C、14N、15N和17O核磁共振谱研究了一些吡啶并呋喃衍生物的呋喃重排

  摘要：

  Pyridofuroxan ([1,2,5]oxodiazolo[3,4-b]pyridine 1-oxide) undergoes isomerization between the N1-oxide and N3-oxide forms which can be observed by the H-1, C-13 and N-15 NMR spectroscopy but not by N-14 and O-17 NMR at ambient and low temperatures. The rearrangement becomes slower at low temperatures and at 233 K H-1 NMR signals for the two structures become observable. H-1, C-13 and N-15 chemical shifts and H-1-H-1, C-13-H-1 and C-13-C-13 coupling constants are used to characterize both forms in the equilibrium mixture. From the H-1 NMR integrals at 233 K equilibrium constants are calculated. Protonation studies using trifluoroacetic acid as a solvent showed the favoured site of protonation to be the pyridine N4 nitrogen atom. DFT shielding calculations are reported for the C-13, N-15 and O-17 nuclei which support the assignments given. From the point of view of structural changes, (1)J(CC) data for 8-nitrotetrazolo[1,5-a]pyridine and o-nitroaminopyridine as precursors of the pyridofuroxans are given for comparison purposes. X-ray diffraction data on 5-methoxypyridofuroxan support the structural results obtained from the NMR investigations. Copyright (C) 2000 John Wiley & Sons, Ltd.

  DOI：

  10.1002/1099-1395(200008)13:8<480::aid-poc268>3.0.co;2-z
• 作为产物：
  描述：

  4-aza-6-nitrobenzofuroxan 以 丙酮 为溶剂， 生成 6-Nitro-[1,2,5]oxadiazolo[3,4-b]pyridine 3-oxide
  参考文献：
  名称：

  1H、13C、14N、15N和17O核磁共振谱研究了一些吡啶并呋喃衍生物的呋喃重排

  摘要：

  Pyridofuroxan ([1,2,5]oxodiazolo[3,4-b]pyridine 1-oxide) undergoes isomerization between the N1-oxide and N3-oxide forms which can be observed by the H-1, C-13 and N-15 NMR spectroscopy but not by N-14 and O-17 NMR at ambient and low temperatures. The rearrangement becomes slower at low temperatures and at 233 K H-1 NMR signals for the two structures become observable. H-1, C-13 and N-15 chemical shifts and H-1-H-1, C-13-H-1 and C-13-C-13 coupling constants are used to characterize both forms in the equilibrium mixture. From the H-1 NMR integrals at 233 K equilibrium constants are calculated. Protonation studies using trifluoroacetic acid as a solvent showed the favoured site of protonation to be the pyridine N4 nitrogen atom. DFT shielding calculations are reported for the C-13, N-15 and O-17 nuclei which support the assignments given. From the point of view of structural changes, (1)J(CC) data for 8-nitrotetrazolo[1,5-a]pyridine and o-nitroaminopyridine as precursors of the pyridofuroxans are given for comparison purposes. X-ray diffraction data on 5-methoxypyridofuroxan support the structural results obtained from the NMR investigations. Copyright (C) 2000 John Wiley & Sons, Ltd.

  DOI：

  10.1002/1099-1395(200008)13:8<480::aid-poc268>3.0.co;2-z