1-(4-cyanophenylmethyl)-4-hexyl-1H-1,2,3-triazole | 1334667-53-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(4-cyanophenylmethyl)-4-hexyl-1H-1,2,3-triazole
• 英文别名: 1-(4-cyanobenzyl)-4-hexyl-1H-1,2,3-triazole；4-[(4-Hexyltriazol-1-yl)methyl]benzonitrile
• CAS: 1334667-53-6
• 化学式: C₁₆H₂₀N₄
• 分子量: 268.362
• InChiKey: ZGXYFECDCPLSPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对氰基溴化苄 在 copper(l) iodide 、 sodium azide 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 1-(4-cyanophenylmethyl)-4-hexyl-1H-1,2,3-triazole
  参考文献：
  名称：

  Synthesis and structure–activity relationship of 1- and 2-substituted-1,2,3-triazole letrozole-based analogues as aromatase inhibitors

  摘要：

  A series of bis- and mono-benzonitrile or phenyl analogues of letrozole 1, bearing (1,2,3 and 1,2,5)-triazole or imidazole, were synthesized and screened for their anti-aromatase activities. The unsubstituted 1,2,3-triazole 10a derivative displayed inhibitory activity comparable with that of the aromatase inhibitor, letrozole I. Compound 10a, bearing a 1,2,3-triazole, is also 10000-times more tightly binding than the corresponding analogue 25 bearing a 1,2,5-triazole, which confirms the importance of a nitrogen atom at position 3 or 4 of the 5-membered ring needed for high activity. The effect on human epithelial adrenocortical carcinoma cell line (H295R) proliferation was also evaluated. The compound 10j (IC50 = 4.64 mu M), a letrozole 1 analogue bearing para-cyanophenoxymethylene-1,2,3-triazole decreased proliferation rates of H295R cells by 76 and 99% in 24 and 72 h respectively. Computer calculations, using quantum ab initio structures, suggest a possible correlation between anti-aromatase activity and the distance between the nitrogen in position 3 or 4 of triazole nitrogen and the cyano group nitrogen. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.05.074

文献信息

• Hybrid NS ligands supported Cu(i)/(ii) complexes for azide–alkyne cycloaddition reactions
  作者：Shi-Qiang Bai、Lu Jiang、Jing-Lin Zuo、T. S. Andy Hor

  DOI：10.1039/c3dt50247c

  日期：——

  Three copper complexes of nitrogen–sulfur donor ligands, [CuBr2(L1)] (1), [CuCl2(L2)2] (2) and [Cu2I2(L3)]n (3) (L1 = bis(2-cyclohexylsulfanylethyl)amine, L2 = 2-(benzylsulfanylmethyl)pyridine and L3 = 2-(4-pyridylsulfanylmethyl)pyridine), have been synthesized and characterized by single-crystal X-ray diffraction (XRD), powder XRD and TGA analysis. Complexes 1 and 2 are mononuclear Cu(II) complexes and are EPR active with distorted square-pyramidal and octahedral geometry, respectively. Complex 3 is a two-dimensional tetrahedral Cu(I) coordination polymer with 16- and 20-membered metallocycles. These complexes show good catalytic activities for one-pot azide–alkyne cycloaddition reactions in CH3OH–H2O.

  三种氮硫供体配体的铜配合物，[CuBr2(L1)] (1)，[CuCL2(L2)2] (2) 和 [Cu2I2(L3)]n (3) (L1 = 双(2-环己硫基乙基)胺，L2 = 2-(苄硫基甲基)吡啶，L3 = 2-(4-吡啶硫基甲基)吡啶)，已通过单晶X射线衍射(XRD)、粉末XRD和TGA分析合成并表征。配合物1和2是单核Cu(II)配合物，并且分别具有扭曲的四角锥体和八面体几何结构，是EPR活性物质。配合物3是具有16和20元金属环的二维四面体Cu(I)配位聚合物。这些配合物在CH3OH-H2O中的一锅叠氮-炔烃环加成反应中显示出良好的催化活性。
• Mechanistic study in azide-alkyne cycloaddition (CuAAC) catalyzed by bifunctional trinuclear copper(I) pyrazolate complex: Shift in rate-determining step
  作者：Vladimir A. Larionov、Anna R. Stashneva、Aleksei A. Titov、Alexey A. Lisov、Michael G. Medvedev、Alexander F. Smol'yakov、Andrey M. Tsedilin、Elena S. Shubina、Victor I. Maleev

  DOI：10.1016/j.jcat.2020.07.010

  日期：2020.10

  Trinuclear copper(I) pyrazolate [Cu(3,5-(CF3)2Pz)]3 was employed in a mechanistic study of azide-alkyne cycloaddition (CuAAC). It was shown that the copper complex operates as a bifunctional catalytic system (copper source and Brønsted base) under mild conditions (RT and air atmosphere) at low catalyst loading (1 mol%). The rate-determining step of the reaction is the first C-N bond formation between

  三核吡唑酸铜（I）[Cu（3,5-（CF 3）2 Pz）] 3被用于叠氮化物-炔烃环加成（CuAAC）的机理研究中。结果表明，铜的络合物在温和的条件下（RT和空气气氛下）以较低的催化剂负载量（1摩尔％）作为双功能催化体系（铜源和布朗斯台德碱）运行。该反应的决定速率的步骤是叠氮化物和乙炔之间的第一个CN键形成（叠氮化物迁移插入），而不是通常认为的乙炔铜（I）形成。观测到的动力学同位素效应等于1.1并通过DFT计算得到了支持。该反应对催化剂浓度具有二级依赖性，这意味着两个铜（I）中心参与了“双蝴蝶”四核配合物Cu 4 L 4（RC≡CH）2形成金属环的步骤在速率确定步骤中。DFT计算证明吡唑酸酯配体充当布朗斯台德碱，使乙炔分子去质子化，提供了成功的催化作用。基于DFT计算已经构​​建了合理的反应催化循环。