4-(2,4-difluorophenyl)-1H-1,2,3-triazole | 1043553-13-4

• 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-(2,4-difluorophenyl)-1H-1,2,3-triazole
• 英文别名: 4-(2,4-difluorophenyl)-2H-triazole
• CAS: 1043553-13-4
• 化学式: C₈H₅F₂N₃
• 分子量: 181.145
• InChiKey: OJPVHXIJJSHOBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(2,4-difluorophenyl)-1H-1,2,3-triazole 、 4-叔丁基苯乙烯 在 N-碘代丁二酰亚胺 作用下， 以 氯仿 为溶剂， 反应 0.17h， 以95%的产率得到2-(1-(4-tert-butylphenyl)-2-iodoethyl)-4-(2,4-difluorophenyl)-2H-1,2,3-triazole
  参考文献：
  名称：

  N²-Selective Iodofunctionalization of Olefins with NH-1,2,3-Triazoles to provide N²-Alkyl-Substituted 1,2,3-Triazoles

  摘要：

  A new method was developed to synthesize N-2-alkyl-substituted 1,2,3-triazole through N-iodosuccinimide (NIS) mediated iodofuctionalization reaction of the alkene group with bi-, mono-, and unsubstituted NH-1,2,3-triazoles. The favored N-1 type hydrogen bond between the iodonium ion intermediate and 1,2,3-triazole was supposed to be generated, which gave the desired N-2-alkyl triazole with a high N-2-selectivity.

  DOI：

  10.1021/acs.joc.6b00185
• 作为产物：
  描述：

  2,4-二氟苯甲醛 在 叠氮基三甲基硅烷 、 ammonium acetate 、 potassium carbonate 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.17h， 生成 4-(2,4-difluorophenyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  使用中孔Pd-MCM-41作为可重复使用的催化剂轻松合成1,3,5-三芳基苯和4-芳基-NH-1,2,3-三唑

  摘要：

  通过β-硝基苯乙烯的反硝化三聚和反硝化反应，开发了介孔Pd-MCM-41催化快速合成1,3,5-三芳基苯和4-芳基NH -1,2,3-三唑。 2]分别将β-硝基苯乙烯与TMSN 3环加成。催化剂可重复使用至少八次，且催化活性损失最小。

  DOI：

  10.1002/ejoc.201801290

文献信息

• Highly N²-Selective Coupling of 1,2,3-Triazoles with Indole and Pyrrole
  作者：Jian Wen、Li-Li Zhu、Qing-Wei Bi、Zhu-Qing Shen、Xiao-Xiao Li、Xin Li、Zhen Wang、Zili Chen

  DOI：10.1002/chem.201302761

  日期：2014.1.20

  Hydrogen‐bond mediated coupling of 1,2,3‐triazoles to indoles and pyrroles results in N2 selective functionalization of the triazole moiety in moderate to excellent yields. The reaction was tolerant of un‐, mono‐ and disubstituted triazoles and was applied to synthesize tryptophan derived fluorescent amino acids.

  氢键介导的1,2,3-三唑与吲哚和吡咯的偶合导致三唑部分的N2选择性官能化，产率中等至优异。该反应可耐受未取代，单取代和双取代的三唑，可用于合成色氨酸衍生的荧光氨基酸。
• Blue Light‐Promoted N−H Insertion of Carbazoles, Pyrazoles and 1,2,3‐Triazoles into Aryldiazoacetates
  作者：Mateus L. Stivanin、Alessandra A. G. Fernandes、Amanda F. Silva、Celso Y. Okada、Igor D. Jurberg

  DOI：10.1002/adsc.201901343

  日期：2020.3.4

  Blue light irradiation of aryldiazoacetates leads to the formation of free carbenes, which can react with carbazoles, pyrazoles and 1,2,3‐triazoles to afford the corresponding N−H inserted products. These reactions are performed under air and at room temperature, allowing the mild preparation of a variety of motifs found in biologically relevant targets.

  芳基重氮乙酸酯的蓝光照射导致形成游离的卡宾，这些卡宾可以与咔唑，吡唑和1,2,3-三唑反应，得到相应的NH插入产物。这些反应在空气和室温下进行，可以温和地制备生物学相关靶标中的各种基序。
• Post-synthetic modification of tryptophan containing peptides via NIS mediation
  作者：Chen-Xue Gu、Qing-Wei Bi、Chu-Kun Gao、Jian Wen、Zhi-Gang Zhao、Zili Chen

  DOI：10.1039/c7ob00329c

  日期：——

  A new efficient method was developed to provide modified tryptophan peptides through NIS (N-iodosuccinimide) mediated N2-selective coupling of a Trp unit with 1,2,3-triazoles, of which, the preliminary spectral properties were also studied.

  开发了一种新的有效方法，以通过NIS（N-碘琥珀酰亚胺）介导的Trp单元与1,2,3-三唑的N 2-选择性偶联提供修饰的色氨酸肽，还研究了其初步的光谱性质。
• Highly N2-Selective Palladium-Catalyzed Arylation of 1,2,3-Triazoles
  作者：Satoshi Ueda、Mingjuan Su、Stephen L. Buchwald

  DOI：10.1002/anie.201103882

  日期：2011.9.12

  Highly N2-selective arylation of 4,5-unsubstituted and 4-substituted 1,2,3-triazoles was achieved for the first time by Pd/L1 catalyst system. A wide range of N2-aryl-1,2,3-triazoles were prepared from aryl bromides, chlorides and triflates with excellent (95–99%) N2-selectivity. DFT calculations suggest that formation of N2-arylated 1,2,3-triazoles is favored kinetically.
• Efficient Synthesis of 2-Substituted-1,2,3-triazoles
  作者：Jarosław Kalisiak、K. Barry Sharpless、Valery V. Fokin

  DOI：10.1021/ol8006748

  日期：2008.8.7

  In this three-component reaction, alkynes undergo a copper(I)-catalyzed cycloaddition with sodium azide and formaldehyde to yield 2-hydroxymethyl-2H-1,2,3-triazoles, which are useful intermediates that can be readily converted to polyfunctional molecules. The hydroxymethyl group can also be removed, providing convenient access to NH-1,2,3-triazoles. The reaction is experimentally simple and readily scalable.