4-acetyl-1-(4-nitrophenyl)-1,2,3-triazole | 117111-00-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-acetyl-1-(4-nitrophenyl)-1,2,3-triazole
• 英文别名: 1-(1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl)ethanone；1-(1-p-nitrophenyl-1H-1,2,3-triazol-4-yl)ethanone；1-(1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl)ethan-1-one；1-[1-(4-Nitrophenyl)triazol-4-yl]ethanone
• CAS: 117111-00-9
• 化学式: C₁₀H₈N₄O₃
• 分子量: 232.199
• InChiKey: SAKOZRVFSWIVCQ-UHFFFAOYSA-N

物化性质

• 熔点：
  233-234 °C
• 沸点：
  445.8±51.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  93.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-acetyl-1-(4-nitrophenyl)-1,2,3-triazole 在 溴 、 溶剂黄146 作用下， 反应 24.0h， 以76%的产率得到1-(1-p-nitrophenyl-1H-1,2,3-triazol-4-yl)-2-bromoethanone
  参考文献：
  名称：

  Hetero-Diels-Alder reactions of novel 3-triazolyl-nitrosoalkenes as an approach to functionalized 1,2,3-triazoles with antibacterial profile

  摘要：

  The generation and reactivity of 3-triazolyl-nitrosoalkenes are reported for the first time. The study showed that hetero-Diels-Alder reaction of these heterodienes is an interesting synthetic strategy to functionalized 1,2,3-triazoles, including 1,2,3-triazolyl-pyrroles, 1,2,3-triazolyl-dipyrromethanes and 1,2,3-triazolyl-indoles. The evaluation of the antibacterial profile against Gram-positive and Gramnegative strains revealed the new 5,5'-diethyldipyrromethane bearing a side chain incorporating a triazole and oxime moieties. The antibacterial profile detected was within the Clinical and Laboratory Standard Institute (CLSI) range and against important Staphylococcus species including Methicillin-resistant strain (S. aureus ATCC 25923, S. epidermidis ATCC 12228 and S. simulans ATCC 27851 and MRSA). Interestingly, this new 1,2,3-triazole presented hemocompatibility and low in silico toxicity profile similar to antibiotics current in use. It also has an usual antibiofilm activity against MRSA, which reinforced its potential as a new antibacterial prototype. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.11.052
• 作为产物：
  描述：

  4-nitrophenyl azide 在 sodium dichromate 、 copper(ll) sulfate pentahydrate 、 硫酸 、 sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 24.5h， 生成 4-acetyl-1-(4-nitrophenyl)-1,2,3-triazole
  参考文献：
  名称：

  Hetero-Diels-Alder reactions of novel 3-triazolyl-nitrosoalkenes as an approach to functionalized 1,2,3-triazoles with antibacterial profile

  摘要：

  The generation and reactivity of 3-triazolyl-nitrosoalkenes are reported for the first time. The study showed that hetero-Diels-Alder reaction of these heterodienes is an interesting synthetic strategy to functionalized 1,2,3-triazoles, including 1,2,3-triazolyl-pyrroles, 1,2,3-triazolyl-dipyrromethanes and 1,2,3-triazolyl-indoles. The evaluation of the antibacterial profile against Gram-positive and Gramnegative strains revealed the new 5,5'-diethyldipyrromethane bearing a side chain incorporating a triazole and oxime moieties. The antibacterial profile detected was within the Clinical and Laboratory Standard Institute (CLSI) range and against important Staphylococcus species including Methicillin-resistant strain (S. aureus ATCC 25923, S. epidermidis ATCC 12228 and S. simulans ATCC 27851 and MRSA). Interestingly, this new 1,2,3-triazole presented hemocompatibility and low in silico toxicity profile similar to antibiotics current in use. It also has an usual antibiofilm activity against MRSA, which reinforced its potential as a new antibacterial prototype. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.11.052

文献信息

• Metal-Free Route for the Synthesis of 4-Acyl-1,2,3-Triazoles from Readily Available Building Blocks
  作者：Joice Thomas、Vince Goyvaerts、Sandra Liekens、Wim Dehaen

  DOI：10.1002/chem.201601928

  日期：2016.7.11

  describe a practical and efficient one‐pot multicomponent reaction for the synthesis of α‐ketotriazoles from readily available building blocks such as methyl ketones, N,N‐dimethylformamide dimethyl acetal, and organic azides with 100 % regioselectivity. This reaction is enabled by the in situ formation of an enaminone intermediate followed by its 1,3‐dipolar cycloaddition reaction with an organic azide

  官能化的1,2,3-三唑杂环已为人们所知，由来已久，并且在从药物化学到材料科学的各种研究领域中都具有非凡的潜力。但是，对治疗重要的1取代的4酰基1H-1，2，3-三唑的研究范围很少，这可能是由于缺乏具有良好范围和实用性的合成方法所致。在这里，我们描述了一种实用且有效的单锅多组分反应，用于从易于获得的结构单元（如甲基酮，N，N）合成α-酮三唑‐二甲基甲酰胺二甲基乙缩醛，以及具有100％区域选择性的有机叠氮化物。此反应可通过原位形成烯胺酮中间体，然后与有机叠氮化物进行1,3-偶极环加成反应来实现。我们有效地利用了开发的策略来衍生化各种杂环和天然产物，该协议很难或不可能通过其他方式实现。
• Microwave Enhancement of a ‘One-Pot’ Tandem Azidation-‘Click’ Cycloaddition of Anilines
  作者：John. Moses、Adam Moorhouse

  DOI：10.1055/s-2008-1078019

  日期：2008.8

  The practical and efficient one-pot azidation of anilines with the reagent combination t-BuONO and TMSN3 has become a useful addition to the click-chemistry toolbox. Herein we report a modification of this methodology, using microwave radiation to significantly enhance the rate of formation of 1,4-triazoles from in situ generated azides.

  一种实用高效的一锅式芳胺叠氮化反应，采用试剂组合t-BuONO和TMSN3，已成为“点击化学”工具箱中的有用补充。在此，我们报告了该方法的一个改进，使用微波辐射显著提高了由原位生成的叠氮化物形成1,4-三唑的速率。
• Synthesis of β-azolyl- and β-azolylcarbonylenamines and their reactions with aromatic azides
  作者：Yuri M. Shafran、Tetyana V. Beryozkina、Ilya V. Efimov、Vasiliy A. Bakulev

  DOI：10.1007/s10593-019-02525-2

  日期：2019.8

  Organocatalytic reactions of 4-acetyl-1,2,3-triazoles with aryl azides were used to obtain bis-1,2,3-triazoles containing directly linked ring systems. The reactions of 4-acetylazoles with DMF–DMA led to the formation of enamines. It was found that the acetyl and methyl groups in 4-acetyl-5-methyl-1,2,3-thiadiazole competed for the role of reactive site. The obtained enamines reacted with aryl azides, forming

  据报道，合成了4-乙酰基取代的唑（1,2,3-三唑，1,2,3-噻二唑和1,2-恶唑）。4-乙酰基1,2,3-三唑与芳基叠氮化物的有机催化反应用于获得含有直接连接的环系统的双1,2,3-三唑。4-乙酰基唑与DMF-DMA的反应导致烯胺的形成。发现4-乙酰基-5-甲基-1,2,3-噻二唑中的乙酰基和甲基竞争反应位点的作用。获得的烯胺与叠氮化物芳基反应，形成通过羰基连接的双环杂环。合成的化合物的结构通过NMR光谱，质谱和X射线结构分析证明。
• Application of novel magnetic H-bonding catalyst for synthesis of hybrid pyridine-triazole derivatives bearing indole or sulfonamide segments
  作者：AmirMahdi Tavassoli、Meysam Yarie、Morteza Torabi、Mohammad Ali Zolfigol

  DOI：10.1016/j.jpcs.2023.111786

  日期：2024.3

  pyridine-triazole derivatives bearing indole or sulfonamide segments via a straightforward multicomponent synthetic strategy. To this end, we devised and synthesized Fe3O4@SiO2@Pr–NHCO–PDCH as a robust and recyclable magnetically active catalyst containing hydrogen bond donor and acceptor sections. Fourier transform-infrared spectroscopy (FT‐IR), elemental mapping, thermogravimetric analysis/derivative thermogravimetry

  在本文中，我们通过简单的多组分合成策略合成了带有吲哚或磺酰胺片段的杂化吡啶三唑衍生物。为此，我们设计并合成了 Fe 3 O 4 @SiO 2 @Pr–NHCO–PDCH 作为一种坚固且可回收的包含氢键供体和受体部分的磁活性催化剂。傅里叶变换红外光谱 (FT-IR)、元素分布、热重分析/导数热重分析 (TGA/DTG)、振动样品磁强计 (VSM)、能量色散X 射线 (EDX)、扫描电子显微镜 (SEM) ）和透射电子显微镜（TEM）来表征催化剂。随后，我们研究了 Fe 3 O 4 @SiO 2 @Pr–NHCO–PDCH 对杂化吡啶体系合成的催化效果。结果表明，协同插烯异头氧化为杂化吡啶-三唑衍生物的合成提供了合理的机理路线。
• Benati, Luisa; Montevecchi, Pier Carlo; Toselli, Maurizio, Journal of the Chemical Society. Perkin transactions I, 1988, p. 1859 - 1864
  作者：Benati, Luisa、Montevecchi, Pier Carlo、Toselli, Maurizio、Spagnolo, Piero

  DOI：——

  日期：——