4-(2-bromophenyl)-1-phenyl-1-H-1,2,3-triazole | 13178-03-5

• 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-bromophenyl)-1-phenyl-1-H-1,2,3-triazole
• 英文别名: 4-(2-bromophenyl)-1-phenyl-1H-1,2,3-triazole；4-(2-bromo-phenyl)-1-phenyl-1H-[1,2,3]triazole；1-Phenyl-4-<2-brom-phenyl>-1,2,3-triazol
• CAS: 13178-03-5
• 化学式: C₁₄H₁₀BrN₃
• 分子量: 300.157
• InChiKey: KPOHHRHQKUESAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30.71
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-(2-bromophenyl)-1-phenyl-1-H-1,2,3-triazole 在 正丁基锂 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 [{C₆H₅{1,2,3-N₃C(o-Ph₂P(C₆H₄))C(PPh₂)}-κ²-P,P}W(CO)₄]
  参考文献：
  名称：

  新的基于1,2,3-三唑的双和三膦配体：合成，过渡金属化学和催化研究。

  摘要：

  三唑基双-和三-膦，5-（二苯基膦基）-1-（2-（二苯基膦基）苯基）-4-苯基-1H-1,2,3-三唑的合成和过渡金属化学（2） ，5-（二苯基膦基）-4-（2-（二苯基膦基）苯基）-1-苯基-1H-1,2,3-三唑（5），1,4-双（2-（二苯基膦基）苯基）-1H描述了-1,2,3-三唑（6）和5-（二苯基膦基）-1,4-双（2-（二苯基膦基）苯基）-1H-1,2,3-三唑（7）。由于存在至少四个供体原子，双膦5和6显示出多种配位行为。发现5和6与VI族金属羰基衍生物的反应对反应条件高度敏感。用[M（CO）4（哌啶）2]处理的双膦5（M = Mo和W）产生P，P和P，N配位化合物[M（CO）4（5）] [M =Mo-κ2 -P，N（8）；W-κ2-P，N（9）；Mo-κ2-P，P（10）; W-κ2-P，P（11）]，而6仅提供P，N配位配合物[{o-Ph2P（C6H4）{1,2,3-

  DOI：

  10.1039/c9dt04302k
• 作为产物：
  描述：

  邻碘溴苯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 、 二异丙胺 作用下， 以 水 、 叔丁醇 为溶剂， 反应 30.92h， 生成 4-(2-bromophenyl)-1-phenyl-1-H-1,2,3-triazole
  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

文献信息

• An Organocatalytic Azide-Aldehyde [3+2] Cycloaddition: High-Yielding Regioselective Synthesis of 1,4-Disubstituted 1,2,3-Triazoles
  作者：Dhevalapally B. Ramachary、Adluri B. Shashank、S. Karthik

  DOI：10.1002/anie.201406721

  日期：2014.9.22

  An organocatalytic azide–aldehyde [3+2] cycloaddition (organo‐click) reaction of a variety of enolizable aldehydes is reported. The organo‐click reaction is characterized by a high rate and regioselectivity, mild reaction conditions, easily available substrates with simple operation, and excellent yields with a broad spectrum of substrates. It constitutes an alternative to the previously known CuAAC

  报道了多种可烯化醛的有机催化叠氮化物-醛[3 + 2]环加成（有机点击）反应。有机点击反应的特点是高速率和区域选择性，温和的反应条件，易于获得的底物和简单的操作，以及具有广泛底物范围的优异收率。它构成了以前已知的CuAAC，RuAAC和IrAAC点击反应的替代方法。
• 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
• Ru^II complexes of 1,2,3-triazole appended tertiary phosphines, [P(Ph){(<i>o</i>-C₆H₄)(1,2,3-N₃C(Ph)CH}₂] and [P(Ph){<i>o</i>-C₆H₄(CCH)-(1,2,3-N₃-Ph)}₂]: highly active catalysts for transfer hydrogenation of carbonyl/nitro compounds and for α-alkylation of ketones
  作者：Pavan K. Namdeo、Sonu Sheokand、Basvaraj S. Kote、Latchupatula Radhakrishna、Harish S. Kunchur、Prateek Saini、Srinivasan Ramakrishnan、Maravanji S. Balakrishna

  DOI：10.1039/d2dt00361a

  日期：——

  to excellent yields. The free energy of β-hydride elimination from the respective Ru-alkoxide intermediates, a key mechanistic step common to all the three catalytic pathways, was calculated to be close to ergoneutral by density functional theory-based calculations, which is posited to rationalize the catalytic activity of 3. The reduction of aromatic nitro compounds was found to be highly chemoselective

  合成两种新的 1,2,3-三唑单膦 [P(Ph)( o -C 6 H 4 )(1,2,3-N 3 C(Ph)CH} 2 ] ( 1 ) 和 [描述了P(Ph) o -C 6 H 4 (CCH)(1,2,3-N 3 -Ph)} 2 ] ( 2 ) 及其 Ru II配合物。1和2与 [Ru( PPh 3 ) 3 Cl 2 ] 以 1:1 的摩尔比产生阳离子配合物3和4， 分别。这两种配合物对转移氢化、硝基还原和α-烷基化反应均表现出非常高的催化活性，并以良好至优异的产率提供了相应的产物。通过基于密度泛函理论的计算，计算出从各自的 Ru-烷氧化物中间体消除 β-氢化物的自由能，这是所有三种催化途径共有的关键机制步骤，接近于人体工学中性，这有望使催化反应合理化3的活动。发现芳族硝基化合物的还原具有高度的化学选择性，即使在羰基存在的情况下也会产生相应的胺作为主要产物。三唑基-N2 配位的 Ru II