N-[6-(3,5-dimethyl-1H-pyrazol-1-yl)-1,2,4,5-tetrazin-3-yl]-4-nitrofurazan-3-amine | 1261061-35-1

• 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: N-[6-(3,5-dimethyl-1H-pyrazol-1-yl)-1,2,4,5-tetrazin-3-yl]-4-nitrofurazan-3-amine
• 英文别名: N-[6-(3,5-dimethylpyrazol-1-yl)-1,2,4,5-tetrazin-3-yl]-4-nitro-1,2,5-oxadiazol-3-amine
• CAS: 1261061-35-1
• 化学式: C₉H₈N₁₀O₃
• 分子量: 304.228
• InChiKey: HOEYUPIQRMHXGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  166
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  3,6-二(3,5-二甲基-1H-吡唑-1-基)-1,2,4,5-四嗪 、 4-氨基-5-硝基呋咱 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 0.8h， 以90%的产率得到N-[6-(3,5-dimethyl-1H-pyrazol-1-yl)-1,2,4,5-tetrazin-3-yl]-4-nitrofurazan-3-amine
  参考文献：
  名称：

  A Mild and Efficient Synthesis of 3-Hetarylamino-s-Tetrazines

  摘要：

  3,6-Bis(3,5-dimethylpyrazol-1-yl)-s-tetrazine reacts with weakly based hetarylamines such as aminofurazans, aminoimidazoles, aminotriazoles, aminotetrazoles, or aminotetrazines on heating in MeCN in the presence of M2CO3 (M = K, Cs) to afford 3-hetarylamino-s-tetrazines, the products of 3,5-dimethylpyrazolyl group displacement.

  DOI：

  10.1016/j.mencom.2012.11.007

文献信息

• Copper-Catalyzed C-N Coupling Reactions of Nitrogen-Rich Compounds - Reaction of Iodofurazans with s-Tetrazinylamines
  作者：Aleksei B. Sheremetev、Nadezhda V. Palysaeva、Marina I. Struchkova、Kyrill Yu. Suponitsky、Mikhail Yu. Antipin

  DOI：10.1002/ejoc.201101732

  日期：2012.4

  Access to unsymmetrical secondary dihetarylamines through the Cu(OAc)2/2-acetylcyclohexanone catalyzed cross-coupling of s-tetrazinylamines with iodofurazans has been developed. The reaction displays good functional group tolerance, involving nitro, azido, and azo groups, which are critical for the construction of energetic materials. Both 3,6-disubstituted and annelated s-tetrazines react readily

  已经开发出通过 Cu(OAc)2/2-乙酰环己酮催化的 s-四嗪基胺与碘呋咱的交叉偶联获得不对称仲二杂芳胺。该反应显示出良好的官能团耐受性，包括硝基、叠氮基和偶氮基团，这些基团对于构建含能材料至关重要。3,6-二取代和退火的 s-四嗪都容易与碘呋喃发生反应以提供所需的产品。
• A Mild and Efficient Synthesis of 3-Hetarylamino-s-Tetrazines
  作者：Aleksei B. Sheremetev、Nadezhda V. Palysaeva、Marina I. Struchkova、Kyrill Yu. Suponitsky

  DOI：10.1016/j.mencom.2012.11.007

  日期：2012.11

  3,6-Bis(3,5-dimethylpyrazol-1-yl)-s-tetrazine reacts with weakly based hetarylamines such as aminofurazans, aminoimidazoles, aminotriazoles, aminotetrazoles, or aminotetrazines on heating in MeCN in the presence of M2CO3 (M = K, Cs) to afford 3-hetarylamino-s-tetrazines, the products of 3,5-dimethylpyrazolyl group displacement.