1-ethyl-5-nitro-1,2,3-triazole

• 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: 1-ethyl-5-nitro-1,2,3-triazole
• 英文别名: 1-Ethyl-5-nitro-1H-1,2,3-triazole；1-ethyl-5-nitrotriazole
• 化学式: C₄H₆N₄O₂
• 分子量: 142.117
• InChiKey: YYOOGTPHUKYWBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  76.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-ethyl-5-nitro-1,2,3-triazole 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 以71.82%的产率得到3-ethyl-1,2,3-triazol-4-amine
  参考文献：
  名称：

  [EN] HETEROCYCLIC INHIBITORS OF EGFR AND/OR HER2, FOR USE IN THE TREATMENT OF CANCER
  [FR] MÉTHODES DE TRAITEMENT DU CANCER

  摘要：

  公开号：

  WO2022076831A3
• 作为产物：
  描述：

  1-tert-butyl-3-ethyl-4-nitro-1,2,3-triazolium perchlorate 在 盐酸 作用下， 以 水 为溶剂， 反应 5.0h， 生成 1-ethyl-5-nitro-1,2,3-triazole
  参考文献：
  名称：

  Acidic N-dealkylation in nitrotriazolium salts

  摘要：

  DOI：

  10.1016/j.mencom.2022.03.020

文献信息

• Synthesis of 1-(Adamantan-1-yl)-1H-1,2,3-Triazoles and their Salts by Adamantylation in AdOH–HClO4 and AdOH–H2SO4 Systems
  作者：Gennady T. Sukhanov、Yuliya V. Filippova、Anna G. Sukhanova、Irina Yu. Bagryanskaya、Konstantin K. Bosov

  DOI：10.1007/s10593-019-02601-7

  日期：2019.12

  ,2,3-triazoles and a series of 1-(adamantan-1-yl)-3-alkyl-1,2,3-triazolium salts were synthesized by regioselective adamantylation of 1,2,3-triazole derivatives. The direction of the attack by the adamantyl cation at the N-1 nitrogen atom and the regioselectivity of the processes of adamantylation and quaternization are ensured by a number of factors: the specificity of the properties of the high-acid

  通过区域选择性合成了1-（金刚烷-1-基）-1 H -1,2,3-三唑和一系列的1-（金刚烷-1-基）-3-烷基-1,2,3-三唑盐1,2,3-三唑衍生物的金刚烷化。金刚烷基阳离子在N-1氮原子上的进攻方向以及金刚烷基化和季铵化过程的区域选择性由许多因素确保：高酸体系AdOH–HClO 4和AdOH–H 2 SO 4以及金刚烷-1-醇的结构特征和高反应活性。
• Selective complexation of 1-ethyl-5-nitro-1,2,3-triazole (entz) with copper(II) salts: Preparation and characterization of [Cu(entz)2Cl2] and [Cu(entz)4(H2O)2](ClO4)2
  作者：Sergei V. Voitekhovich、Juliya V. Filippova、Anna G. Sukhanova、Alexander S. Lyakhov、Ludmila S. Ivashkevich、Gennady T. Sukhanov、Yuri V. Grigoriev

  DOI：10.1016/j.inoche.2012.07.041

  日期：2012.10

  Abstract Treatment of a mixture of isomeric N-ethyl-4(5)-nitro-1,2,3-triazoles with copper(II) chloride or copper(II) perchlorate was found to yield crystalline complexes with 1-ethyl-5-nitro-1,2,3-triazole (entz), namely [Cu(entz)2Cl2] or [Cu(entz)4(H2O)2](ClO4)2, respectively. The obtained complexes, being the rare examples of coordination compounds of vicinal nitrotriazoles, have been characterized

  摘要 用氯化铜 (II) 或高氯酸铜 (II) 处理异构 N-乙基-4(5)-硝基-1,2,3-三唑的混合物，发现与 1-乙基-5-硝基-1,2,3-三唑 (entz)，即分别为 [Cu(entz)2Cl2] 或 [Cu(entz)4(H2O)2](ClO4)2。所得配合物是邻位硝基三唑配位化合物的罕见例子，已通过X射线衍射和热法表征。两种化合物都呈现单核配合物，entz 通过杂环的 N3 原子配位。该配合物在氨水的作用下很容易分解，以高产率生成纯的1-乙基-5-硝基-1,2,3-三唑。络合和去络合反应的连续被证明是分离 1-乙基-5-硝基-1,2、
• Novel Selective Inhibitors of Neutral Endopeptidase for the Treatment of Female Sexual Arousal Disorder. Synthesis and Activity of Functionalized Glutaramides
  作者：David C. Pryde、Graham N. Maw、Simon Planken、Michelle Y. Platts、Vivienne Sanderson、Martin Corless、Alan Stobie、Christopher G. Barber、Rachel Russell、Laura Foster、Laura Barker、Christopher Wayman、Piet Van Der Graaf、Peter Stacey、Debbie Morren、Christopher Kohl、Kevin Beaumont、Sara Coggon、Michael Tute

  DOI：10.1021/jm060133g

  日期：2006.7.1

  Female sexual arousal disorder (FSAD) is a highly prevalent sexual disorder affecting up to 40% of women. We describe herein our efforts to identify a selective neutral endopeptidase (NEP) inhibitor as a potential treatment for FSAD. The rationale for this approach, together with a description of the medicinal chemistry strategy, lead compounds, and SAR investigations are detailed. In particular, the strategy of starting with the clinically precedented selective NEP inhibitor, Candoxatrilat, and targeting low molecular weight and relatively polar mono-carboxylic acids is described. This led ultimately to the prototype development candidate R-13, for which detailed pharmacology and pharmacokinetic parameters are presented.(1)
• Quantum-chemical investigation of certain physicochemical properties of C-nitro-1,2,3-triazole and N-alkyl-4(5)-nitro-1,2,3-triazoles
  作者：O. A. Ivashkevich、Vadim E. Matulis、P. N. Gaponik、G. T. Sukhanov、J. V. Filippova、A. G. Sukhanova

  DOI：10.1007/s10593-009-0210-1

  日期：2008.12

  Quantum-chemical calculations have been carried out on molecular electrostatic potentials, proton affinity in the gas phase, gas phase basicity, and pK (BH+) values in aqueous solution for C-nitro- and N-alkyl-4(5)-nitro-1,2,3-triazoles, and the relative stability of the isomeric N-alkyl-4(5)-nitrotriazoles (alkyl = Me, Et, i-Pr, t-Bu) in the gas phase and in aqueous solution. For all the studied substances in the gas phase the 2H-tautomer and the N(2)-isomers were considerably more stable than the corresponding N(1) compounds, and the 3H-tautomer and N(3)-isomer were the least stable. In aqueous solution 1- and 3-isomers had close values of energies, but in the case of C-nitro-1,2,3-triazole the 1H form became even more stable than the 2H-form. It was established which ring nitrogen atoms of 1,2,3-triazoles are protonated in the gas phase and in solution. The obtained data correlate well with the results of experimental investigations on the alkylation of 1,2,3-triazoles in acidic and basic media and of the experimental investigation on the alkylation of C-nitro-1,2,3-triazoles with diethyl sulfate carried out in the present work.
• N-Alkylation of 4-nitro-1,2,3-triazole revisited. Detection and characterization of the N3-ethylation product, 1-ethyl-5-nitro-1,2,3-triazole
  作者：Sergei V. Voitekhovich、Pavel N. Gaponik、Alexander S. Lyakhov、Juliya V. Filipova、Anna G. Sukhanova、Gennady T. Sukhanov、Oleg A. Ivashkevich

  DOI：10.1016/j.tetlet.2009.03.076

  日期：2009.5

  The products of the alkylation of sodium 4-nitro-1,2,3-triazolate with ethyl bromide were investigated using H-1, C-13, and N-15 NMR spectroscopy. It was found that alkylation proceeds on the triazole nitrogen atoms giving a mixture of three isomeric N-ethyl-4-nitro-1,2,3-triazoles. The molar ratio of N1, N2, and N3-alkylation products was 4:8:1. The formation of a minor N3-isomer, namely 1-ethyl-5-nitro-1,2,3-triazole was confirmed by X-ray structural analysis of single crystals of its tetranuclear copper(II) complex obtained by reaction of copper(II) chloride dihydrate with a mixture of the N2 and N3-isomers. (C) 2009 Elsevier Ltd. All rights reserved.