1-Benzyl-4-(3-ethynylphenyl)triazole | 1429171-97-0

• 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-(3-ethynylphenyl)triazole
• CAS: 1429171-97-0
• 化学式: C₁₇H₁₃N₃
• 分子量: 259.31
• InChiKey: PDWKPEBNNQHVFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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-(3-ethynylphenyl)triazole 、 1-(迭氮基甲基)-4-甲苯 在 copper(l) iodide 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 9.0h， 以357.7 mg的产率得到1-Benzyl-4-[3-[1-[(4-methylphenyl)methyl]triazol-4-yl]phenyl]triazole
  参考文献：
  名称：

  Selective Deprotection of Me₃Si-/Ph₂P(O)-protected Arylalkynes: Methyl Grignard Reagent-promoted Dephosphorylation of Ph₂P(O)-protected Alkynes

  摘要：

  一种Ph2P(O)保护的炔烃在THF中用MeMgBr处理后发生去磷酸化，Me3Si保护未受到影响。该去磷酸化后紧接着与芳基卤化物进行的过渡金属催化偶联反应以一锅法进行，从而获得所需的偶联产物。选择性去保护Me3Si-/Ph2P(O)保护的炔烃使得扩展π系统的合成变得简便，例如环状苯乙炔和不对称取代的二三唑。

  DOI：

  10.1246/cl.140579
• 作为产物：
  描述：

  在 甲基溴化镁 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.5h， 生成 1-Benzyl-4-(3-ethynylphenyl)triazole
  参考文献：
  名称：

  Selective Deprotection of Me₃Si-/Ph₂P(O)-protected Arylalkynes: Methyl Grignard Reagent-promoted Dephosphorylation of Ph₂P(O)-protected Alkynes

  摘要：

  一种Ph2P(O)保护的炔烃在THF中用MeMgBr处理后发生去磷酸化，Me3Si保护未受到影响。该去磷酸化后紧接着与芳基卤化物进行的过渡金属催化偶联反应以一锅法进行，从而获得所需的偶联产物。选择性去保护Me3Si-/Ph2P(O)保护的炔烃使得扩展π系统的合成变得简便，例如环状苯乙炔和不对称取代的二三唑。

  DOI：

  10.1246/cl.140579

文献信息

• Multicomponent click reactions catalysed by copper(I) oxide nanoparticles (Cu2ONPs) derived using Oryza sativa
  作者：Randhir Rai、Dillip Kumar Chand

  DOI：10.1007/s12039-020-01774-5

  日期：2020.12

  found to be effectively stabilizing the nanoparticles from agglomeration. Optical and microscopic techniques were suitably employed for the characterization of the nanoparticles of approximately 10 nm size. Furthermore, the specifically generated nanoparticles were found to be active catalysts in an aqueous medium for Azide-alkyne Huisgen cycloaddition (Click reaction) under base free condition via one-pot

  摘要一种用于充分表征的铜（I）氧化物纳米颗粒（Cu的适宜合成方法2 ONPs）选自Cu通过采用水稻（（II）盐稻）作为减少的廉价的，并准备源以及稳定剂已被证明。明智地选择大米作为催化剂有助于两个事件的共生组合：即淀粉的酸性水解以形成葡萄糖，随后通过原位生成的单糖还原糖（葡萄糖）在形式上还原Cu 2+。碱性条件下生成Cu 2O.此外，还发现大米可有效稳定纳米颗粒的团聚。光学和显微镜技术适合用于表征约10 nm大小的纳米颗粒。此外，发现特定生成的纳米粒子是在水性介质中的活性催化剂，可在无碱条件下通过一锅多组分加成反应合成叠氮化物-炔烃-惠斯根环（点击反应），以合成单-，双-和三- 1,2,3-三唑的产率高至优异。 图形摘要使用水解莱斯合成的Cu 2 ONP，水解莱斯是通过一锅多组分反应在水中合成单，双和三，1,4-二取代的1,2,3-三唑的活性催化剂。
• [Cu8(μ4-H){S2P(OEt)2}6](PF6): A Novel Catalytic Hydride-Centered Copper Cluster for Azide-Alkyne Cycloaddtion
  作者：Bo-Han Lee、Cheng-Chieh Wu、Xuan Fang、C. W. Liu、Jia-Liang Zhu

  DOI：10.1007/s10562-013-0993-7

  日期：2013.6

  A hydride-centered dithiophosphate cluster [Cu-8(mu(4)-H)S2P(OEt)(2)}(6)](PF6) (1)] previously developed by us was applied as a new catalyst to the 1,3-dipolar cycloaddition of organic azides and alkynes for preparing substituted trizoles. With the required catalyst loading as low as 0.4 mol%, the reactions of terminal alkynes with BnN3 all proceeded smoothly at ambient temperature in CH3CN to exclusively produce 1,4-triazoles in good yields. For these reactions, it is assumed that the formation of the requisite copper acetylide intermediate is facilitated by the abstraction of the terminal hydrogen of alkynes by the hydride released from the central of the cluster. With only few examples being documented in literatures, the reactions of a range of internal alkynes have also been realized under the catalysis of 1 (0.8 mol%) in DMF at elevated temperature, to yield 1,4,5-trisubstituted triazoles in moderate to high yields. Our study has provided a preliminary insight into the effect of sulfur-based ligands on the activity of copper ion.
• Fluorinated Anions Promoted “on Water” Activity of Di- and Tetranuclear Copper(I) Catalysts for Functional Triazole Synthesis
  作者：Sayantani Saha、Mandeep Kaur、Jitendra K. Bera

  DOI：10.1021/acs.organomet.5b00348

  日期：2015.6.22

  A set of di- and tetra-copper(I) compounds [Cu-2((LH)-H-1)(2)][BArF](2) (1) ((LH)-H-1 = bis(5,7-dimethyl-1,8-naphthyridin-2-yl)amine; BArF = [BC6H3(CF3)(2)}(4)]) and [Cu-4(L-1)(2)(L-2)(2)][BNBF](2) (2) (L-2 = 5,7-dimethyl-1,8-naphthyridin-2-amine; BNBF = [NH2B(C6F5)(3)}(2)]), stabilized by naphthyridine-based ligands and containing fluorinated anions, is synthesized. Their catalytic utility for copper(I)-catalyzed azidealkyne coupling (CuAAC) reactions in organic solvents and on water is evaluated. The dimer analogue [Cu-2((LH)-H-1)(2)][BPh4](2) (3) with nonfluorinated anion is synthesized for the purpose of comparison. All three compounds show CuAAC activity in organic solvents, although the performance of 3 is considerably lower. Remarkable rate enhancement is displayed by compounds containing fluorinated anions (1 and 2) under on water conditions for the model reaction involving benzyl azide, affording 98% conversions in 1520 min, where compound 3 gives 76% conversions in 50 min. Kinetic experiments reveal the involvement of two coppers in the cycloaddition process. Employing a host of substrates, the usefulness of fluorinated anions to dramatically improve the catalytic activity of Cu(I) compounds under on water conditions is demonstrated.