N-(2-iodophenyl)-2-azidoacetamide | 1251394-84-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(2-iodophenyl)-2-azidoacetamide
• 英文别名: 2-azido-N-(2-iodophenyl)acetamide
• CAS: 1251394-84-9
• 化学式: C₈H₇IN₄O
• 分子量: 302.074
• InChiKey: CBZNDUBPPRSZRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  43.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-iodophenyl)-2-azidoacetamide 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 9.0h， 生成 2-hydroxymethyl-1,2,3-triazolo[5,1-d][1,4]benzodiazepin-2-one
  参考文献：
  名称：

  Three-Step Synthesis of Triazolobenzodiazepinones via Sonogashira/Huisgen Protocol

  摘要：

  The sequential Sonogashira coupling/intramolecular azide cycloaddition (Huisgen cycloaddition) protocol was performed onto N-(2-iodophenyl)-2-azidoacetamide as the acyclic precursor giving tricyclic 1,2,3-triazolo-[5,1-d][1,4]benzodiazepin-2-ones. These target products were thus obtained through a three-step synthesis in variable yields depending upon the substituent placed onto the acetylenic counterpart. The influence of catalyst concentration, reaction temperature and reaction medium upon cycloadduct yields were also studied.

  DOI：

  10.3987/com-13-12752
• 作为产物：
  描述：

  2-碘苯胺 在 sodium azide 、 三乙胺 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 2.67h， 生成 N-(2-iodophenyl)-2-azidoacetamide
  参考文献：
  名称：

  Three-Step Synthesis of Triazolobenzodiazepinones via Sonogashira/Huisgen Protocol

  摘要：

  The sequential Sonogashira coupling/intramolecular azide cycloaddition (Huisgen cycloaddition) protocol was performed onto N-(2-iodophenyl)-2-azidoacetamide as the acyclic precursor giving tricyclic 1,2,3-triazolo-[5,1-d][1,4]benzodiazepin-2-ones. These target products were thus obtained through a three-step synthesis in variable yields depending upon the substituent placed onto the acetylenic counterpart. The influence of catalyst concentration, reaction temperature and reaction medium upon cycloadduct yields were also studied.

  DOI：

  10.3987/com-13-12752

文献信息

• The azide–alkyne cycloaddition catalysed by transition metal oxide nanoparticles
  作者：Giorgio Molteni、Anna M. Ferretti、Mario Italo Trioni、Fausto Cargnoni、Alessandro Ponti

  DOI：10.1039/c9nj04690a

  日期：——

  Colloidal nanoparticles of Earth-abundant, first-row transition metal oxides and sulfide, namely magnetite (Fe3O4), manganese and cobalt ferrite, (MnFe2O4, CoFe2O4), manganese(II) oxide (MnO) and sulfide (α-MnS), were used as catalysts in the cycloaddition between azides and methyl propiolate. The presence of these nanoparticles allowed us to carry out the cycloadditions under milder conditions and

  富含地球的第一行过渡金属氧化物和硫化物的胶体纳米颗粒，即磁铁矿（Fe 3 O 4），锰和钴铁氧体（MnFe 2 O 4，CoFe 2 O 4），锰（II）氧化物（MnO）和硫化物（α-MnS）在叠氮化物和丙酸甲酯之间的环加成反应中用作催化剂。这些纳米粒子的存在使我们能够在较温和的条件下进行环加成反应，其区域选择性可与经典的“无金属”热过程相媲美。铁氧体纳米颗粒比MnO和α-MnS纳米颗粒具有更高的转化率。还证明了环加成到1，2-二取代的乙炔上的可行性。铁氧体纳米催化剂可以磁性回收和再利用，而不会显着降低催化活性。密度泛函理论（DFT）计算支持一种机械假说，该假说将增加的环加成率归因于叠氮化物在纳米催化剂表面上的吸附。
• Exploring of N-phthalimide-linked 1,2,3-triazole analogues with promising ­anti-SARS-CoV-2 activity: synthesis, biological screening, and molecular modelling studies
  作者：Ateyatallah Aljuhani、Mosa Alsehli、Mohamed A. Seleem、Shaya Y. Alraqa、Hany E. A. Ahmed、Nadjet Rezki、Mohamed R. Aouad

  DOI：10.1080/14756366.2024.2351861

  日期：2024.12.31

  In this study, a library of phthalimide Schiff base linked to 1,4-disubstituted-1,2,3-triazoles was designed, synthesised, and characterised by different spectral analyses. All analogues have been ...

  在这项研究中，设计、合成了与 1,4-二取代-1,2,3-三唑连接的邻苯二甲酰亚胺席夫碱库，并通过不同的光谱分析进行了表征。所有类似物都已...
• Silver(I) oxide nanoparticles as a catalyst in the azide–alkyne cycloaddition
  作者：Anna M. Ferretti、Alessandro Ponti、Giorgio Molteni

  DOI：10.1016/j.tetlet.2015.08.083

  日期：2015.10

  1,3-Dipolar cycloadditions between a number of azides and monosubstituted acetylenes have been carried out in the presence of catalytic amounts of silver(l) oxide nanoparticles. 4-Substituted 1,2,3-triazoles were usually the only products, while the presence of electron-withdrawing groups onto the azide moiety caused a loss of regioselectivity giving mixtures of 4- and 5-substituted 1,2,3-triazoles. A novel catalytic cycle has been proposed to rationalize this latter 'non-click' behaviour. (C) 2015 Elsevier Ltd. All rights reserved.