3-(3,5-dimethylpyrazol-1-yl)-6-(2-hydroxyethylamino)-1,2,4,5-tetrazine | 270588-53-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四嗪
• 英文名称: 3-(3,5-dimethylpyrazol-1-yl)-6-(2-hydroxyethylamino)-1,2,4,5-tetrazine
• 英文别名: (6-(3,5-dimethyl-1H-pyrazol-1-yl)-1,2,4,5-tetrazin-3-ylamino)methanol；2-[6-(3,5-dimethylpyrazol-1-yl)[1,2,4,5]tetrazin-3-ylamino]ethanol；6-(3,5-Dimethyl-1H-pyrazol-1-yl)-N-(2-hydroxyethyl)-1,2,4,5-tetrazine-3-amine；2-[[6-(3,5-dimethylpyrazol-1-yl)-1,2,4,5-tetrazin-3-yl]amino]ethanol
• CAS: 270588-53-9
• 化学式: C₉H₁₃N₇O
• 分子量: 235.249
• InChiKey: DISIXRIZRGLBHZ-UHFFFAOYSA-N

物化性质

• 沸点：
  500.6±52.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-(3,5-dimethylpyrazol-1-yl)-6-(2-hydroxyethylamino)-1,2,4,5-tetrazine 在 硝酸 作用下， 以43%的产率得到2-{[6-(3,5-dimethyl-1H-pyrazol-1-yl)-1,2,4,5-tetrazin-3-yl](nitro)amino}ethyl nitrate
  参考文献：
  名称：

  Synthesis and Properties of Alkylnitramino-1,2,4,5-Tetrazines

  摘要：

  The peculiarities of the nitration reaction under acidic conditions were studied for a series of alkylamino-1,2,4,5-tetrazines. It was found that the extent of N,N'-dialkyl-1,2,4,5-tetrazine-3,6-diamine nitration was determined by the concentration of nitric acid and the selection of alkyl substituents at the exocyclic nitrogen atom. A new method was developed for the preparation of unsymmetrically substituted N,N'-dialkyl-1,2,4,5-tetrazine-3,6-diamines from N-nitro derivatives of N-alkyl-1,2,4,5-tetrazin-3-amines.

  DOI：

  10.1007/s10593-014-1448-9
• 作为产物：
  描述：

  3,6-bis(3,5-dimethylpyrazol-1-yl)-1,2-dihydro-1,2,4,5-tetrazine 在 溶剂黄146 、 sodium nitrite 作用下， 以 N-甲基吡咯烷酮 、 乙腈 为溶剂， 反应 3.0h， 生成 3-(3,5-dimethylpyrazol-1-yl)-6-(2-hydroxyethylamino)-1,2,4,5-tetrazine
  参考文献：
  名称：

  Syntheses and Crystal Structures of Two Unsymmetrical 1,2,4,5-tetrazine Derivatives

  摘要：

  两种不对称的 1,2,4,5-四嗪衍生物，(6-(3,5-二甲基-1H-吡唑-1-基)-1,2,4,5-四嗪-3-基氨基)甲醇（C9H13N7O，3）和 4-(6-(3,5-二甲基-1H-吡唑-1-基)-1,2,4,5-四嗪-3-基)吗啉（C11H15N7O，4）、由 3,6-双（3,5-二甲基-1H-吡唑-1-基）-1,2,4,5-四嗪和相应的脂肪族胺（分别为 2-氨基乙醇和吗啉）合成，其结构已通过单晶 X 射线衍射方法得到证实。晶体结构显示，化合物 3 通过分子间 O-H-N、N-H-O 氢键和 π-π 相互作用而稳定，而化合物 4 则通过 π-π 相互作用而稳定。结构分析表明，化合物 3 属于单斜体系，空间群为 P2(1)/c，晶体数据 a = 6.979(2) Å, b = 9.563(3) Å, c = 16.542(5) Å, V = 1084.4(5) Å3, Z = 4, F(000) = 496, R 1 = 0.0488, wR 2 = 0.1063.化合物 4 属于正方晶系，空间群为 P2(1)2(1)2(1)，晶体数据 a = 6.544(14) Å, b = 12.085(3) Å, c = 15.753(4) Å, V = 1245.7(5) Å3, Z = 4, F(000) = 552, R 1 = 0.0403, wR 2 = 0.0913.

  DOI：

  10.1007/s10870-012-0287-8

文献信息

• Synthesis, structures, and magnetic properties of crystals of dinuclear copper(II) and cobalt(II) complexes with 3-(3,5-dimethylpyrazol-1-yl)-6-R-1,2,4,5-tetrazines
  作者：E. V. Cherdantseva、D. V. Starichenko、P. A. Slepukhin、R. I. Ishmetova、Yu. N. Shvachko、A. V. Korolev、G. L. Rusinov、V. V. Ustinov、A. I. Matern、V. N. Charushin

  DOI：10.1007/s11172-010-0152-x

  日期：2010.4

  Dinuclear complexes of CuII with 3-(3,5-dimethylpyrazol-1-yl)-6-(2-hydroxyethylami-no)-1,2,4,5-tetrazine (1) and CoII with 3-(3,5-dimethylpyrazol-1-yl)-6-(piperidin-1-yl)-1,2,4,5- tetrazine (2) were synthesized and structurally characterized, and the magnetic (SQUID) and resonance (EPR) properties of van der Waals crystals based on these complexes were studied. Unusual behavior of the effective magnetic moment μeff(T) is observed at T < 60 K. A nonmonotonic increase in μeff(?) for 1 (s~6 %) and a 20% reduction of μeff(?) for 2 have a common origin and are due to the influence of spin-orbital coupling on the character of the splitting between the t2g and eg levels of the central ion. Distortions of the coordination site “switch on” a positive (1) or negative (2) contribution of the orbital magnetic moment near 6 K. Irreversible temperature behavior of μeff(T) in the heating and cooling regimes in the vicinity of 60 K suggests that the character of structural distortions and the magnetic properties are related to ligand geometry. This factor plays a significant role in crystal engineering of magnetoactive structures with polynitrogen ligands.

  研究人员合成了 CuII 与 3-(3,5-二甲基吡唑-1-基)-6-(2-羟乙基氨基)-1,2,4,5-四嗪 (1) 的双核配合物，以及 CoII 与 3-(3,5-二甲基吡唑-1-基)-6-(哌啶-1-基)-1,2,4,5-四嗪 (2) 的双核配合物、5- tetrazine (2) 进行了合成和结构表征，并研究了基于这些配合物的范德华晶体的磁性（SQUID）和共振（EPR）特性。1的μeff(?)非单调增加（s~6%）和2的μeff(?)减少20%有着共同的原因，都是由于自旋轨道耦合对中心离子的t2g和eg电平之间分裂特性的影响。配位位点的畸变在 6 K 附近 "开启 "了轨道磁矩的正（1）或负（2）贡献。μeff(T) 在 60 K 附近的加热和冷却状态下的不可逆温度行为表明，结构畸变的特征和磁性与配体的几何形状有关。这一因素在多氮配体磁活性结构的晶体工程中发挥着重要作用。
• Synthesis of Highly Substituted Pyridazines through Alkynyl Boronic Ester Cycloaddition Reactions
  作者：Matthew D. Helm、Jane E. Moore、Andrew Plant、Joseph P. A. Harrity

  DOI：10.1002/anie.200500288

  日期：2005.6.20
• Synthesis of 1,2,4,5-tetrazines, symmetrically and unsymmetrically 3,6-disubstituted by N-nucleophiles
  作者：G. L. Rusinov、N. I. Latosh、I. I. Ganebnykh、R. I. Ishmetova、N. K. Ignatenko、O. N. Chupakhin

  DOI：10.1134/s1070428006050198

  日期：2006.5

  6-R-3-(3,5-Dimethylpyrazol-1-yl)-1,2,4,5-tetrazines with aliphatic, cycloaliphatic, and aromatic amines, and also with NH-heterocycles undergo a nucleophilic substitution of the dimethylpyrazole moiety yielding symmetrically and unsymmetrically substituted 1,2,4,5-tetrazines. In the 3,6-diimidazolyl- and 3,6-dibenzotriazolyl derivatives reactions of nucleophilic substitution of the heterocyclic moiety also occur. In some cases an ipsosubstitution of amino, hydrazino, and azido groups is observed.
• Latosh; Rusinov; Ganebnykh, Russian Journal of Organic Chemistry, 1999, vol. 35, # 9, p. 1363 - 1371
  作者：Latosh、Rusinov、Ganebnykh、Chupakhin

  DOI：——

  日期：——
• On the composition of copper(II), cobalt(II), and nickel(II) complexes with some 3,6-disubstituted 1,2,4,5-tetrazines
  作者：E. V. Cherdantseva、A. V. Nesterova、A. I. Matern、L. Yu. Buldakova、M. Yu. Yanchenko、R. I. Ishmetova、G. L. Rusinov

  DOI：10.1134/s1070363210090240

  日期：2010.9

  Complex formation in the systems containing copper(II), cobalt(II) and nickel(II) ions (M) and 3(3,5-dimethylpyrazol-1-yl)-6-R-1,2,4,5-tetrazines (R = 2-hydroxyethylamino, piperidino) (L) was studied by voltammetry and spectrophotometry. Cu(II), Co(II) and Ni(II) were found to form complex compounds with derivatives of 1,2,4,5-tetrazine with the ratio of the components M:L = 1:1. The complex stability constants