1-苄基-4-(4-氟苯基)-1,2,3-三唑 | 1007604-01-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-苄基-4-(4-氟苯基)-1,2,3-三唑
• 英文名称: 1-benzyl-4-(4-fluorophenyl)-1,2,3-triazole
• 英文别名: 1-benzyl-4-(4-fluorophenyl)-1H-1,2,3-triazole；1-benzyl-4-(p-fluorophenyl)-1,2,3-triazole；1-Benzyl-4-(4-fluorophenyl)triazole
• CAS: 1007604-01-4
• 化学式: C₁₅H₁₂FN₃
• 分子量: 253.279
• InChiKey: IGZVVEKYIUQAQU-UHFFFAOYSA-N

物化性质

• 熔点：
  113-115 °C
• 沸点：
  434.9±47.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 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：
  3

反应信息

• 作为反应物：
  描述：

  1-苄基-4-(4-氟苯基)-1,2,3-三唑 、 trimethoxonium tetrafluoroborate 以 二氯甲烷 为溶剂， 以85%的产率得到
  参考文献：
  名称：

  Introducing Axial Chirality into Mesoionic 4,4′-Bis(1,2,3-triazole) Dicarbenes

  摘要：

  Mesoionic 4,4'-bis(1,2,3-triazole-5,5'-diylidene) Rh(I) complexes having a C2 chiral 4,4'-axis were accessed from 3-alkyltriazolium salts in virtually complete de. Their structure and configurational integrity were assessed by NMR spectroscopy, X-ray crystallography, and chiral HPLC. Computational analysis of the MICs involved in the reaction suggested the formation of a highly stable and unprecedented cation-carbene intermediate species, which could be evidenced experimentally by cyclic voltammetry analysis.

  DOI：

  10.1021/ol3004657
• 作为产物：
  描述：

  苄基叠氮 在 bis(triphenylphosphine)nickel(II) chloride 、 四丁基氟化铵 、 copper diacetate 、 sodium ascorbate 、 三环己基膦 作用下， 以 四氢呋喃 为溶剂， 生成 1-苄基-4-(4-氟苯基)-1,2,3-三唑
  参考文献：
  名称：

  4-Organochalcogenoyl-1H-1,2,3-triazoles: synthesis and functionalization by a nickel-catalyzed Negishi cross-coupling reaction

  摘要：

  A general method for the synthesis of triazoles containing selenium and tellurium was accomplished via a CuCAAC reaction between organic azides and a terminal triple bond, generated by in situ deprotection of the silyl group. The reaction tolerates alkyl and arylazides, with alkyl and aryl substituents directly bonded to the chalcogen atom. The products were readily functionalized by a nickel-catalyzed Negishi cross-coupling reaction, furnishing the aryl-heteroaryl products at the 4-position in good yields. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.09.062

文献信息

• Copper-Catalyzed Huisgen and Oxidative Huisgen Coupling Reactions Controlled by Polysiloxane-Supported Amines (AFPs) for the Divergent Synthesis of Triazoles and Bistriazoles
  作者：Zhan-Jiang Zheng、Fei Ye、Long-Sheng Zheng、Ke-Fang Yang、Guo-Qiao Lai、Li-Wen Xu

  DOI：10.1002/chem.201202472

  日期：2012.10.29

  click reactions mediated by a polysiloxane‐supported secondary amine allow the preparation of novel heterocyclic compounds, that is, bistriazoles. Comparably, it is also surprising that the use of a diamine‐functional polysiloxane as ligand led to a classic Huisgen [3+2] cycloaddition in excellent yields. From the results of the present amine‐functional polysiloxanes‐controlled Huisgen reaction or oxidative

  在点击化学中成功地提出了一个有趣的例子，该例子采用铜（I）和胺官能大分子聚硅氧烷体系发散催化。在本手稿中，我们证明了仲胺官能聚硅氧烷在叠氮化物和炔烃的铜介导的惠斯根反应中诱导氧化偶联的显着能力，从而获得了良好的收率和选择性。由聚硅氧烷负载的仲胺介导的点击反应可制备新型杂环化合物，即双三唑。相比之下，使用二胺官能化聚硅氧烷作为配体也导致了经典的Huisgen [3 + 2]环加成反应，且收率很高，这也令人惊讶。
• Synthesis and Characterization of Copper(I)‐Cysteine Complex Supported on Magnetic Layered Double Hydroxide as an Efficient and Recyclable Catalyst System for Click Chemistry Using Choline Azide as Reagent and Reaction Medium
  作者：Farzane Pazoki、Arefe Salamatmanesh、Sepideh Bagheri、Akbar Heydari

  DOI：10.1007/s10562-019-03011-2

  日期：2020.4

  Abstract In this study, Fe 3 O 4 @LDH@cysteine–Cu(I) nanoparticles as a novel and recyclable catalytic system was designed and successfully synthesized. These nanoparticles show high catalytic activity for preparation of the triazole family through reaction of the organic halides with alkynes in the presence of choline azide as reagent and reaction medium. In addition, Fe 3 O 4 @LDH@cysteine–Cu(I)

  摘要 在本研究中，设计并成功合成了 Fe 3 O 4 @LDH@半胱氨酸-Cu(I) 纳米粒子作为一种新型可回收的催化体系。这些纳米颗粒在叠氮化胆碱作为试剂和反应介质的情况下，通过有机卤化物与炔烃的反应，对制备三唑族显示出高催化活性。此外，Fe 3 O 4 @LDH@cysteine-Cu(I) 可以很容易地回收和重复使用五次，催化活性没有任何显着损失。图形摘要
• Dual roles of substituted thiourea as reductant and ligand in CuAAC reaction
  作者：Siyu Wang、Kai Jia、Jiajia Cheng、Yu Chen、Yaofeng Yuan

  DOI：10.1016/j.tetlet.2017.08.029

  日期：2017.9

  efficient catalytic system, CuSO4·5H2O/1-(4-methoxyphenyl)-3-phenylthiourea, for the copper(I)-catalyzed azide–alkyne cycloaddition reaction (CuAAC) was discovered. In the above catalytic system, substituted thiourea acts both as a reductant and a ligand. CuSO4·5H2O/1-(4-methoxyphenyl)-3-phenylthiourea is both an economical and efficient catalyst for the CuAAC reaction. In addition, the new catalytic system

  发现了一种高效的催化体系CuSO 4 ·5H 2 O / 1-（4-甲氧基苯基）-3-苯基硫脲，用于铜（I）催化的叠氮化物-炔烃环加成反应（CuAAC）。在上述催化体系中，取代的硫脲既充当还原剂又充当配体。CuSO 4 ·5H 2 O / 1-（4-甲氧基苯基）-3-苯基硫脲是CuAAC反应的经济有效的催化剂。此外，新的催化系统具有有利的功能，包括温和的绿色反应条件以及广泛的底物相容性。用CuSO 4 ·5H 2制备了各种具有良好产率的1,4-二取代的1,2,3-三唑O / 1-（4-甲氧基苯基）-3-苯基硫脲在水溶液中的催化体系。
• Synthesis and characterization of active cuprous oxide particles and their catalytic application in 1,2,3‐triazole synthesis via alkyne‐azide cycloaddition reaction in water
  作者：Micky Lanster Sawkmie、Dipankar Paul、Gitumoni Kalita、Khushboo Agarwala、Pradip K. Maji、Paresh Nath Chatterjee

  DOI：10.1002/jhet.3723

  日期：2019.12

  the catalytic prowess of the various cuprous oxide materials in the cycloaddition reaction of alkynes and azides to synthesize 1,4‐disubstituted‐1,2,3‐triazoles. A wide variety of substitutions can nicely be tolerated in our optimized reaction conditions to produce very good to excellent yields of the corresponding triazoles in water at 55 °C. The reactions are carried out in water without any assistance

  活性氧化亚铜材料由CuSO 4 .5H 2合成在各种稳定剂（即十六烷基三甲基溴化铵，十二烷基硫酸钠和聚乙烯吡咯烷酮）存在下，使用亚锡酸钠作为还原剂。合成的氧化亚铜材料通过粉末X射线衍射和傅立叶变换红外光谱法得到了很好的表征，以确定它们的身份，而场发射扫描电子显微镜和能量色散光谱法分别研究了它们的形态和组成。我们已经比较了各种氧化亚铜材料在炔烃和叠氮化物的环加成反应中催化合成1,4-二取代-1,2,3-三唑的催化能力。在我们优化的反应条件下，可以很好地耐受各种各样的取代反应，从而在55°C的水中产生非常好至极好的相应三唑收率。反应在水中进行而无需有机助溶剂或其他添加剂的任何辅助，这使得催化方法既经济又环保。
• An efficient and recyclable thiourea-supported copper(<scp>i</scp>) chloride catalyst for azide–alkyne cycloaddition reactions
  作者：Milan Kr. Barman、Ashish Kumar Sinha、Sharanappa Nembenna

  DOI：10.1039/c5gc02545a

  日期：——

  A reaction between two equivalents of bulky thiourea i.e., 1-3-bis(2,6-dimethylphenyl)thiourea(L) [L = (ArNH)2C=S); (Ar = 2,6-Me2C6H3)}] and CuCl2 or CuCl in THF solvent afforded a bulky thiourea stabilized copper(I) halide...

  两当量的大体积硫脲之间的反应，即1-3-双（2,6-二甲基苯基）硫脲（L）[L = （（ArNH）2C = S）; （Ar = 2,6-Me2C6H3）}]和CuCl2或CuCl在THF溶剂中的溶液，得到了庞大的硫脲稳定的卤化铜（I）...