1-ethyl-4-nitro-1,2,3-triazole | 107945-67-5

• 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-4-nitro-1,2,3-triazole
• 英文别名: 1-ethyl-4-nitro-1H-1,2,3-triazole；1-Ethyl-4-nitro-1H-1,2,3-triazole；1-ethyl-4-nitrotriazole
• CAS: 107945-67-5
• 化学式: C₄H₆N₄O₂
• 分子量: 142.117
• InChiKey: VBFITRYPXPRYRG-UHFFFAOYSA-N

物化性质

• 熔点：
  78.5-79 °C(Solv: ethanol (64-17-5))
• 沸点：
  282.4±32.0 °C(Predicted)
• 密度：
  1.52±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 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-4-nitro-1,2,3-triazole 在 palladium on activated charcoal 、 氢气 作用下， 以 乙醇 为溶剂， 40.0 ℃ 、344.75 kPa 条件下， 反应 3.0h， 生成 1-乙基-1H-1,2,3-噻唑-4-胺
  参考文献：
  名称：

  [EN] INHIBITORS OF GLYCOGEN SYNTHASE 1 (GYS1) AND METHODS OF USE THEREOF
  [FR] INHIBITEURS DE LA GLYCOGÈNE SYNTHASE 1 (GYS1) ET LEURS MÉTHODES D'UTILISATION

  摘要：

  本文提供了公式(I')的化合物或其立体异构体或互变异构体，或任何其药学上可接受的盐，其中Y2，Y3，L1，L2，X1，X2，X3，X4，X5，Q1，R1，R2，Rk，Rm和Rn的定义在本文其他部分中已经说明。本文还提供了制备公式(F)化合物的方法。本文还提供了抑制GYS1的方法以及治疗需要该方法的个体中的GYS1介导的疾病，障碍或状况的方法。

  公开号：

  WO2022198196A1
• 作为产物：
  描述：

  1,3-diethyl-4-nitro-1,2,3-triazolium perchlorate 在 盐酸 作用下， 以 水 为溶剂， 反应 18.0h， 生成 1-ethyl-4-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

• 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、
• [EN] INHIBITORS OF GLYCOGEN SYNTHASE 1 (GYS1) AND METHODS OF USE THEREOF<br/>[FR] INHIBITEURS DE LA GLYCOGÈNE SYNTHASE 1 (GYS1) ET LEURS MÉTHODES D'UTILISATION
  申请人：MAZE THERAPEUTICS INC

  公开号：WO2022198196A1

  公开（公告）日：2022-09-22

  Provided herein are compounds of formula (I') or a stereoisomer or tautomer thereof, or a pharmaceutically acceptable salt of any of the foregoing, wherein Y2, Y3, L1, L2, X1, X2, X3, X4, X5, Q1, R1, R2, Rk, Rm, and Rnare as defined elsewhere herein. Also provided herein are methods of preparing compounds of formula (F). Also provided herein are methods of inhibiting GYS1 and methods of treating a GYS1 -mediated disease, disorder, or condition in an individual in need thereof.

  本文提供了公式(I')的化合物或其立体异构体或互变异构体，或任何其药学上可接受的盐，其中Y2，Y3，L1，L2，X1，X2，X3，X4，X5，Q1，R1，R2，Rk，Rm和Rn的定义在本文其他部分中已经说明。本文还提供了制备公式(F)化合物的方法。本文还提供了抑制GYS1的方法以及治疗需要该方法的个体中的GYS1介导的疾病，障碍或状况的方法。
• 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.
• Reactions of 4-nitro-1,2,3-triazole with alkylating agents and compounds with activated multiple bonds
  作者：L. I. Vereshchagin、N. I. Kuznetsova、L. P. Kirillova、V. V. Shcherbakov、G. T. Sukhanov、G. A. Gareev

  DOI：10.1007/bf00522733

  日期：1986.7
• 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.