(±)-4-phenyl-1-(1-phenylethyl)-1H-1,2,3-triazole

• 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-phenyl-1-(1-phenylethyl)-1H-1,2,3-triazole
• 英文别名: rac-4-phenyl-1-(1-phenylethyl)-1H-1,2,3-triazole；4-phenyl-1-(1-phenyl-ethyl)-1H-1,2,3-triazole；4-phenyl-1-(1-phenylethyl)-1H-[1,2,3]triazole；4-phenyl-1-(1-phenylethyl)-1H-1,2,3-triazole；4-phenyl-1-(1-phenylethyl)-1H-1,2,3-trizole；4-Phenyl-1-(1-phenylethyl)triazole
• 化学式: C₁₆H₁₅N₃
• 分子量: 249.315
• InChiKey: XPKPVMSCCYSANP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  (±)-4-phenyl-1-(1-phenylethyl)-1H-1,2,3-triazole 在 三氟甲苯 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 为溶剂， 反应 90.33h， 生成 (3-methyl-4-phenyl-1-(1-phenylethyl)-1H-1,2,3-triazol-3-ium-5-yl)trihydroborate
  参考文献：
  名称：

  Mesoionic Carbene–Boranes

  摘要：

  Mesoionic carbenes (MICs), derived from alkylation and deprotonation of triazoles, are shown to form stable complexes with BH3. The synthesis of triazoles via Huigsen cycloadditions provides considerable structural diversity. Several routes to MIC-boranes are described, and their structures have been characterized by X-ray crystallography. As predicted on the basis of the increased sigma-donor capacity of MICs by comparison to NHCs, the MIC-borane adducts are more reactive reducing agents.

  DOI：

  10.1021/om400743c
• 作为产物：
  描述：

  (1-溴乙基)苯 在 sodium azide 、 [5-(3-(2(S)-methylbutyl)imidazol-2-yliden-1-yl)-25,26,27,28-tetrapropyloxycalix[4]arene]copper bromide 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 24.08h， 生成 (±)-4-phenyl-1-(1-phenylethyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  带有NHC–杯芳烃单元的铜络合物：点击化学的合成与应用†

  摘要：

  报道了杯[4]芳烃负载的N-杂环卡宾（NHC）铜配合物的合成。通过常规程序制备单取代的杯[4]芳烃，然后连接咪唑基以产生NHC配体的前体。用两个烷​​基溴化物进行烷基化，然后进行金属化，得到了特征充分的原始配合物。X射线结构显示出铜的“外”构象。在点击化学中研究了配合物的催化活性，并显示出良好的性能。特别是，在无溶剂条件下和快速的反应时间下，高收率合成了三种新的三唑。测试了新合成的手性配合物的消旋叠氮化物的动力学拆分。

  DOI：

  10.1039/c6nj02089e

文献信息

• Copper(II) Triflate as a Double Catalyst for the One-Pot Click Synthesis of 1,4-Disubstituted 1,2,3-Triazoles from Benzylic Acetates
  作者：Shin-ichi Fukuzawa、Eiji Shimizu、Satoshi Kikuchi

  DOI：10.1055/s-2007-986638

  日期：2007.9

  Copper(II) triflate doubly catalyzed the substitution of benzylic acetates by TMSN3 and the subsequent 1,3-dipolar addition with an alkyne in one pot. This procedure afforded the preparation of 1,4-disubstituted 1,2,3-triazoles in good yields starting from the easily accessible acetates without isolating an organic azide ­using a single catalyst.

  铜(II)三氟甲磺酸盐双重催化苄基乙酸酯与TMSN3的取代反应，以及随后与炔烃的一锅法1,3-偶极加成反应。该过程以良好产率制备了易于获得的乙酸酯为起始物，无需分离有机叠氮化合物，仅使用单一催化剂即可合成1,4-二取代的1,2,3-三唑。
• Carboxylic Acid-Promoted Copper(I)-Catalyzed Azide−Alkyne Cycloaddition
  作者：Changwei Shao、Xinyan Wang、Jimin Xu、Jichen Zhao、Qun Zhang、Yuefei Hu

  DOI：10.1021/jo101495k

  日期：2010.10.15

  presence of carboxylic acids and the latter two steps can be promoted significantly by carboxylic acids. Benzoic acid showed the best promotion activity, and the acids with strong chelating ability to Cu(I) ion could not serve for this purpose. Thus, the first carboxylic acid-promoted highly efficient CuAAC was established.

  在本文中，我们证明了CuAAC催化循环中的所有三个关键步骤都可以在羧酸存在下进行，而后两个步骤可以被羧酸显着促进。苯甲酸显示出最佳的促进活性，而对Cu（I）离子具有强螯合能力的酸不能用于此目的。因此，建立了第一种羧酸促进的高效CuAAC。
• Acid–Base Jointly Promoted Copper(I)-Catalyzed Azide–Alkyne Cycloaddition
  作者：Changwei Shao、Xinyan Wang、Qun Zhang、Sheng Luo、Jichen Zhao、Yuefei Hu

  DOI：10.1021/jo200869a

  日期：2011.8.19

  In this novel acid–base jointly promoted CuAAC, the combination of CuI/DIPEA/HOAc was developed as a highly efficient catalytic system. The functions of DIPEA and HOAc have been assigned, and HOAc was recognized to accelerate the conversions of the C–Cu bond-containing intermediates and buffer the basicity of DIPEA. As a result, all drawbacks occurring in the popular catalytic system CuI/NR3 were overcome

  在这种新型的酸碱共同促进的CuAAC中，CuI / DIPEA / HOAc的结合被开发为一种高效的催化体系。已经指定了DIPEA和HOAc的功能，HOAc被认为可以加速含C–Cu键的中间体的转化并缓冲DIPEA的碱性。结果，容易克服了流行的催化体系CuI / NR 3中发生的所有缺点。
• Ruthenium-Catalyzed Alkenylation of Arenes with Alkynes or Alkenes by 1,2,3-Triazole-Directed C-H Activation
  作者：Xing Guang Li、Kai Liu、Gang Zou、Pei Nian Liu

  DOI：10.1002/ejoc.201402938

  日期：2014.12

  The ruthenium-catalyzed alkenylation of arenes with alkynes or alkenes has been achieved by using 1,2,3-triazole as the directing group for the C–H activation. With [Ru(p-cymene)Cl2]2 as the catalyst and Cu(OAc)2·H2O and AgSbF6 as additives, various triazole-substituted arenes reacted readily with a range of internal alkynes or terminal alkenes to afford di- or monoalkenylated arenes with high regioselectivity

  通过使用 1,2,3-三唑作为 C-H 活化的导向基团，已经实现了钌催化芳烃与炔烃或烯烃的烯基化。以 [Ru(p-cymene)Cl2]2 作为催化剂，Cu(OAc)2·H2O 和 AgSbF6 作为添加剂，各种三唑取代的芳烃很容易与一系列内部炔烃或末端烯烃反应得到二或单烯基化的芳烃具有高区域选择性和中等至优异的产率。
• Highly efficient click reaction on water catalyzed by a ruthenium complex
  作者：Hai Xiao Siyang、Hui Ling Liu、Xin Yan Wu、Pei Nian Liu

  DOI：10.1039/c4ra12960a

  日期：——

  The highly efficient click reaction between terminal alkynes and azides has been achieved on water using ruthenium complex RuH2(CO)(PPh3)3 as the catalyst, and the catalyst loading was decreased to 0.2 mol% on water from 5 mol% in organic solvent. The RuH2(CO)(PPh3)3/H2O system also catalyzed the one-pot click reaction of bromides, sodium azide and alkynes; in this process, azides formed in situ and

  使用钌配合物RuH 2（CO）（PPh 3）3作为催化剂，在水上实现了末端炔烃与叠氮化物之间的高效点击反应，并且在水中，催化剂的载量从5 mol％降低至0.2 mol％。溶剂。RuH 2（CO）（PPh 3）3 / H 2 O体系还催化了溴化物，叠氮化钠和炔烃的一锅法点击反应。在此过程中，叠氮化物就地形成，然后与炔烃发生点击反应。在这两种含水过程中，均以50-89％的产率获得了1,4-二取代的1,2,3-三唑，具有很高的区域选择性。