1-benzyl-4-(2-bromophenyl)-1H-1,2,3-triazole | 1253116-74-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-benzyl-4-(2-bromophenyl)-1H-1,2,3-triazole
• 英文别名: 1-Benzyl-4-(2-bromophenyl)triazole；1-benzyl-4-(2-bromophenyl)triazole
• CAS: 1253116-74-3
• 化学式: C₁₅H₁₂BrN₃
• 分子量: 314.184
• InChiKey: WOOQFYUCKYNUTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-benzyl-4-(2-bromophenyl)-1H-1,2,3-triazole 、 2,6-二甲基苯胺 在 1,1'-双(二苯基膦)二茂铁 、 palladium diacetate 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 48.08h， 以60.3%的产率得到2,6-dimethyl-N-[2-(1-benzyl-1H-1,2,3-triazol-4-yl)phenyl]aniline
  参考文献：
  名称：

  Photoluminescent Copper(I) Complexes with Amido-Triazolato Ligands

  摘要：

  A series of heteroleptic copper(I) complexes incorporating amido-triazole and diphosphine ligands, [Cu-I(N-phenyl-2-(1-phenyl-1H-1,2,3-triazol-4-yl)aniline)(dppb)] (1), [Cu-I(N-(4-methylphenyl)-2-(1-phenyl-1H-1,2,3-triazol-4-yl)aniline)(dppb)] (2), [Cu-I(N-(4-methoxyphenyl)-2-(1-phenyl-1H-1,2,3-triazol-4-yl)aniline)(dppb)] (3), [Cu-I(N-(4-chlorophenyl)-2-(1-phenyl-1H-1,2,3-triazol-4-yl)aniline)(dppb)] (4), [Cu-I(2,6-dimethyl-N-[2-(1-phenyl-1H-1,2,3-triazol-4-yl)phenynaniline)(dppb)] (5), [Cu-I(2,6-dimethyl-N-[2-(1-benzyl-1H-1,2,3-triazol-4-yl)phenyl]aniline)(dppb)] (6), (dppb = 1,2-bis(diphenylphosphino)benzene), have been prepared. The complexes adopt a distorted tetrahedral geometry in the solid state with the amido-triazole ligand forming a six-member ring with the Cu(I) ion. The complexes exhibit long-lived photoluminescence with colors ranging from yellow to red-orange in the solid state, in frozen glass at 77 K, and in fluid solution with modest quantum yields of up to 0.022. Electrochemically, complexes 1-4 show irreversible oxidation waves while 5 and 6 are characterized by quasi-reversible oxidations as determined by cyclic voltammetry. For 1-4, the emission energy and oxidation potential are found to vary linearly with the Hammett parameter sigma(p) of the substituent in the para position of the amido ligand, while in 5 and 6, large differences in emission are observed because of the nature of N3 substitution in the triazole ring. Density functional theory calculations have been performed on the singlet ground states (S-o) of all complexes at the BP86/6-31G(d) level to assist in assignment of the excited states. On the basis of both experimental and computational results, we have assigned the excited states as intraligand + metal-to-ligand charge transfer (3)(ILCT+MLCT) or ligand-to-ligand charge transfer mixed with MLCT (3)(MLCT+LLCT) in these complexes.

  DOI：

  10.1021/ic102338g
• 作为产物：
  描述：

  2-溴苯乙炔 、 苄基叠氮 在 C₁₃₅H₂₁₆CuN₁₀O₁₀₂⁽¹⁺⁾ 作用下， 以 水 为溶剂， 以80 %的产率得到1-benzyl-4-(2-bromophenyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  用于水相 CuAAC 反应的环糊精基多功能超分子催化剂

  摘要：

  CuAAC反应作为一种优异的生物正交反应，在生物学研究中得到了广泛的应用。本工作以不同方式合成了三种环糊精衍生物β-CD-3、β-CD-4和CD-P。其中，使用微量的β-CD-3可以在温和条件下有效促进CuAAC反应。仅使用20 ppm浓度的β-CD-3-Cu(I)，反应的TON就高达45,000，并且催化剂在反复循环后仍然具有较高的催化活性，这可能归因于其配位形成的螯合结构铜比 β-CD-4-Cu(I) 和 CD-P-Cu(I) 更稳定。此外，我们还证明超分子催化体系的构建可以在超低浓度下有效实现细胞外点击反应，

  DOI：

  10.1016/j.apcata.2023.119309

文献信息

• 1-D copper(I) coordination polymer based on bidentate 1,3-dithioether ligand: Novel catalyst for azide-alkyne-cycloaddition (AAC) reaction
  作者：Sankar Saha、Kinkar Biswas、Basudeb Basu

  DOI：10.1016/j.tetlet.2018.05.040

  日期：2018.6

  A novel 1,3-bis(4-fluorophenylthio)-propane ligand based CuI 1-D polymeric coordination complex having formula ([(CuI)2ArS(CH2)3SAr}2]n, Ar = 4-F-C6H4) has been synthesized and characterized by 1H NMR, 13C NMR and single crystal XRD techniques. This complex has been employed for the first time as suitable catalyst for base-free one-pot three-component regioselective azide-alkyne cycloaddition (AAC)

  基于式（[（CuI）2 ArS（CH 2）3 SAr} 2 ] n，Ar = 4-FC 6的新型的1,3-双（4-氟苯硫基）丙烷配体的CuI 1-D聚合物配位络合物H 4）已经合成并通过1 H NMR，13 C NMR和单晶XRD技术表征。该络合物首次用作无碱单锅三组分区域选择性叠氮化物-炔烃环加成（AAC）反应的合适催化剂。还使用我们的催化体系通过一锅两步反应以多组分方式制备了具有硫官能化侧链的新型1,2,3-三唑化合物。
• A facile synthesis of 5-amino-[1,2,3]triazolo[5,1-a]isoquinoline derivatives through copper-catalyzed cascade reactions
  作者：Yunfeng Chen、Shilei Zhou、Shan Ma、Wenqian Liu、Zhiquan Pan、Xiaodong Shi

  DOI：10.1039/c3ob41774c

  日期：——

  A copper-catalyzed cascade method was developed for the synthesis of [1,2,3]triazolo[5,1-a]isoquinoline derivatives. The N-fused heterocycles were obtained in good to excellent yields under mild conditions, which provided a new strategy for the preparation of this highly functionalized building block.

  开发了一种铜催化的级联方法，用于合成[1,2,3]三唑并[5,1- a ]异喹啉衍生物。在温和的条件下以高至极好的收率获得了N稠合杂环，这为制备这种高度官能化的结构单元提供了新的策略。
• Activating Azides and Alkynes for the Click Reaction with [Cu( <i>a</i> NHC) ₂ I] or [Cu( <i>a</i> NHC) ₂ ] ⁺ ( <i>a</i> NHC = Triazole‐Derived Abnormal Carbenes): Structural Characterization and Catalytic Properties
  作者：Stephan Hohloch、Damaris Scheiffele、Biprajit Sarkar

  DOI：10.1002/ejic.201300150

  日期：2013.8.6

  single-crystal X-ray diffraction analyses. In 6, the copper(I) center is tricoordinated, and its geometry is in between trigonal planar and T-shaped. In halide-free 11, the copper(I) center is linearly coordinated by two abnormal-carbene ligands. All complexes were tested as catalysts in the Huisgen [3+2] cycloaddition reaction between azides and alkynes, and they showed excellent efficiencies under neat conditions

  中性含碘铜 (I) 络合物 [Cu(aNHC)2I] aNHC = 1-benzyl-3-methyl-4-phenyl-1,2,3-triazol-5-ylidene (for 6) 和 3-甲基-1-[2-(甲硫基)苯基]-4-苯基-1,2,3-triazol-5-ylidene (for 7)} 和阳离子、无卤化物的铜 (I) 配合物 [Cu(aNHC)2 ](BF4) aNHC = 1-benzyl-3-methyl-4-phenyl-1,2,3-triazol-5-ylidene (for 8), 3-methyl-1,4-diphenyl-1,2,3 -triazol-5-ylidene (for 9), 3-methyl-1-[2-(methylthio)phenyl]-4-phenyl-1,2,3-triazol-5-ylidene (for 10), and 1-mesityl
• A novel benzimidazole based ionic liquid-tagged Schiff base copper catalyst: Synthesis, characterization and application toward the synthesis of 1,4-disubstituted 1,2,3-triazoles
  作者：Mintu Thakur、Prasun Choudhury、Ambica Kejriwal、Ayan Mukherjee、Kinkar Biswas

  DOI：10.1016/j.ica.2023.121405

  日期：2023.5

  A novel benzimidazole ionic liquid tagged Schiff base and its copper catalyst was synthesized and characterized by various techniques (FTIR, NMR, FESEM, TEM, XPS and pXRD). The new Cu(I) catalyst (Cu@ILSB) was used in the three-component synthesis of 1,4-disubstituted 1,2,3-triazole derivatives via ‘click’ (azide-alkyne cycloaddition, AAC) reaction under ambient conditions. A library of functionalized

  合成了一种新型苯并咪唑离子液体标记席夫碱及其铜催化剂，并通过各种技术（FTIR、NMR、FESEM、TEM、XPS 和 pXRD）对其进行了表征。新型 Cu(I) 催化剂 (Cu@ILSB) 用于在环境条件下通过“点击”（叠氮-炔环加成，AAC）反应合成 1,4-二取代 1,2,3-三唑衍生物的三组分. 合成了功能化的 1,2,3-三唑库。通过可回收性实验确定了 Cu 催化剂的非均质性。这种离子液体标记的席夫碱基铜催化剂可能首先应用于一锅法 AAC 反应。
• One-Pot Three-Step Synthesis of 1,2,3-Triazoles by Copper-Catalyzed Cycloaddition of Azides with Alkynes formed by a Sonogashira Cross-Coupling and Desilylation
  作者：Frédéric Friscourt、Geert-Jan Boons

  DOI：10.1021/ol1022036

  日期：2010.11.5

  A microwave-assisted, one-pot, three-step Sonogashira cross-coupling-desilylation-cycloaddition sequence was developed for the convenient preparation of 1,4-disubstituted 1,2,3-triazoles starting from a range of halides, acyl chlorides, ethynyltrimethylsilane, and azides.