1-(4-isopropylbenzyl)-4-phenyl-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: 1-(4-isopropylbenzyl)-4-phenyl-1H-1,2,3-triazole
• 英文别名: 4-Phenyl-1-[(4-propan-2-ylphenyl)methyl]triazole；4-phenyl-1-[(4-propan-2-ylphenyl)methyl]triazole
• 化学式: C₁₈H₁₉N₃
• 分子量: 277.369
• InChiKey: UOZMWWOAFKCUMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  溴苯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 copper(II) sulfate 、 sodium ascorbate 、 三乙胺 作用下， 以 水 、 叔丁醇 为溶剂， 生成 1-(4-isopropylbenzyl)-4-phenyl-1H-1,2,3-triazole
  参考文献：
  名称：

  1-Benzyl-4-phenyl-1H-1,2,3-triazoles improve the transcriptional functions of estrogen-related receptor γ and promote the browning of white adipose

  摘要：

  The estrogen-related receptor gamma (ERR gamma) is a potential molecular target for the development of small molecules to stimulate the adipose browning process, which may represent a novel attractive strategy to treat obesity related disorders. The receptor possesses a very small ligand binding cavity and therefore identification of small molecule ERR gamma modulators is a considerable challenge. We have successfully designed and synthesized a series of 1-benzyl-4-phenyl-1H-1,2,3-triazoles and demonstrated that they improve the transcriptional functions of ERR gamma, potently elevating both the mRNA levels and the protein levels of ERR gamma downstream targets. One of the most promising compounds, 4-(1-(4-iso-propylbenzyl)-1H-1,2,3-triazol-4-yl)benzene-1,2-diol (2e) was further shown to directly bind with the ERR gamma ligand binding domain (ERR gamma-LBD) in an isothermal calorimetric (ITC) assay and to thermally stabilize ERR gamma-LBD protein by increasing its melting temperature (T-m) as demonstrated by circular dichroism (CD) spectroscopy. Furthermore, 2e potently stimulates the adipocyte browning process and induces mitochondrial biogenesis both in vitro and in vivo, suggesting the considerable therapeutic potential of this compound for the treatment of obesity and related disorders. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.03.082

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。
• An efficient (NHC) Copper (I)-catalyst for azide–alkyne cycloaddition reactions for the synthesis of 1,2,3-trisubstituted triazoles: Click chemistry
  作者：Nedra Touj、Ismail Özdemir、Sedat Yaşar、Naceur Hamdi

  DOI：10.1016/j.ica.2017.06.065

  日期：2017.10

  methods, mass spectrometry (EI-MS and HRMS) and elemental analysis. These novel cupper complexes 3 – 4 were used as a catalyst for alkyne – azide cycloaddition (CuAAC) reaction. Several triazoles 7 have been synthesized. This catalytic system fulfils the requirements of “click chemistry” with its mild and convenient conditions, notably in water at room temperature with low catalyst loading and simple isolation

  摘要在本研究中，由5，6-二甲基-1-（烷基苄基）-1 H-苯并[d]咪唑与各种烷基卤反应，合成了一系列新的苯并咪唑盐（2a – c）。这些盐用于合成铜N-杂环卡宾（Cu-NHC）配合物3-4。通过FT-IR，NMR（1 H和13 C）光谱法，质谱（EI-MS和HRMS）和元素分析对获得的（NHC）铜（I）配合物3-4进行表征。这些新型的铜配合物3-4被用作炔烃-叠氮化物环加成（CuAAC）反应的催化剂。已经合成了几种三唑7。该催化系统以其温和且方便的条件满足“点击化学”的要求，特别是在室温下的水中，催化剂负载量低，分离简单，无需纯化步骤。
• 1-Benzyl-4-phenyl-1H-1,2,3-triazoles improve the transcriptional functions of estrogen-related receptor γ and promote the browning of white adipose
  作者：Shilin Xu、Liufeng Mao、Ping Ding、Xiaoxi Zhuang、Yang Zhou、Lei Yu、Yingxue Liu、Tao Nie、Tingting Xu、Yong Xu、Jinsong Liu、Jeff Smaill、Xiaomei Ren、Donghai Wu、Ke Ding

  DOI：10.1016/j.bmc.2015.03.082

  日期：2015.7

  The estrogen-related receptor gamma (ERR gamma) is a potential molecular target for the development of small molecules to stimulate the adipose browning process, which may represent a novel attractive strategy to treat obesity related disorders. The receptor possesses a very small ligand binding cavity and therefore identification of small molecule ERR gamma modulators is a considerable challenge. We have successfully designed and synthesized a series of 1-benzyl-4-phenyl-1H-1,2,3-triazoles and demonstrated that they improve the transcriptional functions of ERR gamma, potently elevating both the mRNA levels and the protein levels of ERR gamma downstream targets. One of the most promising compounds, 4-(1-(4-iso-propylbenzyl)-1H-1,2,3-triazol-4-yl)benzene-1,2-diol (2e) was further shown to directly bind with the ERR gamma ligand binding domain (ERR gamma-LBD) in an isothermal calorimetric (ITC) assay and to thermally stabilize ERR gamma-LBD protein by increasing its melting temperature (T-m) as demonstrated by circular dichroism (CD) spectroscopy. Furthermore, 2e potently stimulates the adipocyte browning process and induces mitochondrial biogenesis both in vitro and in vivo, suggesting the considerable therapeutic potential of this compound for the treatment of obesity and related disorders. (C) 2015 Elsevier Ltd. All rights reserved.