1-phenyl-4-(thiophen-2-yl)-1H-1,2,3-triazole | 1391823-60-1

• 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-phenyl-4-(thiophen-2-yl)-1H-1,2,3-triazole
• 英文别名: 1-phenyl-4-thiophen-2-yltriazole
• CAS: 1391823-60-1
• 化学式: C₁₂H₉N₃S
• 分子量: 227.29
• InChiKey: CBGQAQPLISQPPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  59
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-乙酰基噻吩 在 copper diacetate 、 三甲基乙酸 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 12.0h， 生成 1-phenyl-4-(thiophen-2-yl)-1H-1,2,3-triazole
  参考文献：
  名称：

  铜介导的N-甲苯磺酰hydr和苯胺合成1,2,3-三唑

  摘要：

  NNNifty目标：在1,4-二取代和1,4,5-三取代的1,2,3-三唑，容易获得的苯胺和一个简单的铜介导的合成Ñ -tosylhydrazone基板至C后行环化 N和N  Ñ键的形成（参见方案； Piv =新戊酰基，Ts =对甲苯磺酰基）。该方法可以在温和条件下高效地制备1,2,3-三唑，而无需使用叠氮化物。

  DOI：

  10.1002/anie.201306416

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。
• Metal-Free CN- and NN-Bond Formation: Synthesis of 1,2,3-Triazoles from Ketones,<i>N</i>-Tosylhydrazines, and Amines in One Pot
  作者：Zhengkai Chen、Qiangqiang Yan、Zhanxiang Liu、Yuhong Zhang

  DOI：10.1002/chem.201405057

  日期：2014.12.22

  A novel synthetic approach toward 1,4‐disubstituted 1,2,3‐triazoles by CN‐ and NN‐bond formation has been established under transition‐metal‐free conditions. Complete control of the regioselectivity was successfully achieved. Commercially available anilines, ketones, and N‐tosylhydrazine were treated with molecular iodine in one pot to allow the regioselective generation of 1,4‐disubstituted 1,2

  在无过渡金属的条件下，已经建立了一种通过CN和NN键形成1,4-二取代的1,2,3-三唑的新颖合成方法。成功实现了对区域选择性的完全控制。在一个锅中用分子碘处理市售的苯胺，酮和N-甲苯磺酰肼，从而可以在不使用叠氮化物的情况下高选择性地生成1,4-二取代的1,2,3-三唑。
• Thiophene-based donor–acceptor co-oligomers by copper-catalyzed 1,3-dipolar cycloaddition
  作者：Stefanie Potratz、Amaresh Mishra、Peter Bäuerle

  DOI：10.3762/bjoc.8.76

  日期：——

  Herein we present a three-component one-pot procedure to synthesize co-oligomers of a donor–acceptor–donor type, in which thiophene moieties work as donor and 1,2,3-triazoles as acceptor units. In this respect, terminally ethynylated (oligo)thiophenes were coupled to halogenated (oligo)thiophenes in the presence of sodium azide and a copper catalyst. Optoelectronic properties of various thiophene-1,2,3-triazole co-oligomers were investigated by UV–vis spectroscopy and cyclic voltammetry. Several co-oligomers were electropolymerized to the corresponding conjugated polymers.

  在这里，我们提出了一种三组分一锅法合成供体-受体-供体类型的共寡聚物的方法，其中噻吩基团作为供体，1,2,3-三唑作为受体单元。在这方面，末端乙炔基化的(寡)噻吩与卤代的(寡)噻吩在氮化钠和铜催化剂的存在下偶联。通过紫外-可见光谱和循环伏安法研究了各种噻吩-1,2,3-三唑共寡聚物的光电性质。几种共寡聚物被电聚合成相应的共轭聚合物。
• A two-step continuous flow synthesis of 1,4-disubstituted 1,2,3-triazoles under metal- and azide-free conditions
  作者：Jiajia Gu、Zheng Fang、Zhao Yang、Xin Li、Ning Zhu、Li Wan、Ping Wei、Kai Guo

  DOI：10.1039/c6ra19022g

  日期：——

  A green, general and efficient I2/TBHP mediated synthetic method toward 1,4-disubstituted 1,2,3-triazoles via the reactions of acetophenones, tosylhydrazine and anilines within 35 min in a two-step continuous flow system has been developed. The reaction proceeds smoothly to afford 1,4-disubstituted 1,2,3-triazoles in moderate to good yield under metal- and azide-free conditions by using I2 as a catalyst

  开发了一种绿色，通用，有效的I 2 / TBHP介导的方法，该方法通过乙苯，甲苯磺酰肼和苯胺在两步连续流系统中于35分钟内反应生成1,4-二取代的1,2,3-三唑。反应平稳进行，通过使用I 2作为催化剂，在无金属和叠氮化物的条件下以中等至良好的产率得到1，4-二取代的1,2,3-三唑。
• A ferrocene functionalized Schiff base containing Cu(<scp>ii</scp>) complex: synthesis, characterization and parts-per-million level catalysis for azide alkyne cycloaddition
  作者：Firdaus Rahaman Gayen、Abdul Aziz Ali、Debashree Bora、Saptarshi Roy、Supriya Saha、Lakshi Saikia、Rajib Lochan Goswamee、Biswajit Saha

  DOI：10.1039/d0dt00915f

  日期：——

  catalysis chemistry. Using the minimum amount of catalyst to obtain the maximum product yield is of the utmost priority in catalysis, which drives us to use parts-per-million (ppm) levels of catalyst loadings in syntheses. In this context, a new ferrocene functionalized Schiff base and its copper(ii) complex have been synthesized and characterized. This Cu(ii) complex is employed as a catalyst for popular

  原子经济是发展催化化学的主要因素之一。在催化中，使用最小量的催化剂以获得最大的产物收率是最重要的，这促使我们在合成中使用百万分之（ppm）的催化剂负载量。在这种情况下，已经合成并表征了新的二茂铁官能化的席夫碱及其铜（ii）配合物。这种Cu（ii）配合物被用作流行的“点击化学”的催化剂，其中1,2,3-三唑是最终产物。低至5 ppm的催化剂负载量足以生产出克级的产品，并且分别实现了140 000和70 000 h-1的最高周转数（TON）和周转频率（TOF）值。此外，