1-(4-bromophenyl)-4-butyl-1H-[1,2,3]triazole | 879012-79-0

• 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-(4-bromophenyl)-4-butyl-1H-[1,2,3]triazole
• 英文别名: 1-(4-bromophenyl)-4-butyl-1H-1,2,3-triazole；1-(4-bromophenyl)-4-butyltriazole
• CAS: 879012-79-0
• 化学式: C₁₂H₁₄BrN₃
• 分子量: 280.167
• InChiKey: QPQJBKGFJXNKHM-UHFFFAOYSA-N

物化性质

• 沸点：
  376.8±44.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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-(4-bromophenyl)-4-butyl-1H-[1,2,3]triazole 在 四丁基氟化铵 、 palladium diacetate 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 生成 4-Butyl-1-(4-ethynyl-phenyl)-1H-[1,2,3]triazole
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of 1-Phenyl-1H-1,2,3-triazoles as Selective Insect GABA Receptor Antagonists

  摘要：

  To study the interaction of phenylheterocycles with gamma-aminobutyric acid (GABA) receptors, 4- or 5-alkyl(or phenyl)-1-phenyl-1 H-1,2,3-triazoles were synthesized and examined for their ability to inhibit the specific binding of [H-3]-4'-ethynyl-4-n-propylbicycloorthobenzoate (EBOB), a noncompetitive antagonist, to the housefly and rat GABA receptors, as well as to the beta 3 subunit homo-oligomer of the human GABA receptor investigated as a model receptor. 4-Substituted 1-phenyl-1 H-1,2,3-triazoles were found to be more potent competitive inhibitors than the 5-substituted regioisomers in the case of all receptors. The 4-tert-butyl or 4-n-propyl analogue of 1-(2,6-dichloro-4-trifluoromethylphenyl)1 H-1,2,3-triazole exhibited the highest level of inhibition of [H-3]EBOB binding to all receptors. Most of the synthesized analogues were more active in terms of the inhibition of EBOB binding to the housefly and human beta 3 GABA receptors than to the rat receptor. The 4-cyclohexyl analogue showed the highest (185-fold) housefly versus rat receptor selectivity. A three-dimensional quantitative structure-activity relationship (3D-QSAR) analysis demonstrated that both the 4-trifluoromethyl-2,6dichloro substitution on the phenyl ring and a small, bulky, hydrophobic substituent at the 4-position of the triazole ring played significant roles in conferring high potency in cases involving the housefly and human beta 3 receptors. The human beta 3 receptor resembled the housefly receptor in terms of their recognition of phenyltriazoles, whereas 3D-QSAR analysis revealed a slight difference between the two receptors in terms of their mechanisms of recognition of the para-substituent on the phenyl moiety. Some of the triazoles synthesized here exhibited insecticidal activity, which was correlated with their ability to inhibit [H-3]EBOB binding to the housefly receptor. Thus, 1-phenyl-1 H-1,2,3-triazoles with the appropriate substituents exert insecticidal activity by selectively acting at the site for noncompetitive antagonism of insect GABA receptors.

  DOI：

  10.1021/jf052773i
• 作为产物：
  描述：

  1-叠氮基-4-溴苯 、 1-己炔 在 nickel oxide supported on rice hulk derived silica catalyst 作用下， 以 水 为溶剂， 反应 10.0h， 以57%的产率得到1-(4-bromophenyl)-4-butyl-1H-[1,2,3]triazole
  参考文献：
  名称：

  可再生 SiO2 作为 NiO 催化剂的载体，用于在水介质中通过叠氮化物-炔烃环加成区域选择性合成 1,4-二取代 1,2,3-三唑

  摘要：

  源自稻壳的 SiO 2 (SiO 2 -RH )已被用作 NiO 催化剂的载体，用于 60 °C 水介质中的叠氮化物-炔烃环加成反应。10wt%NiO/SiO 2 -RH 催化剂被发现是区域选择性合成 1,4-二取代 1,2,3-三唑的有效且可重复使用的催化剂，其底物范围广泛，包括碳水化合物三唑和一锅法合成三唑类。反应机理遵循NiO/SiO 2 -RH催化剂表面的镍π-络合物。催化剂循环使用多达四次，显示出一致的活性和选择性。BET-SA、H 2 -TPR、NH 3建立了构效关系和机理研究-TPD、SEM-EDX、XPS、XRD、29 Si SS MAS NMR 和H 2脉冲化学吸附研究和合理的反应机理已被提出。

  DOI：

  10.1016/j.mcat.2022.112191

文献信息

• Benedict's solution/ vitamin C: An alternative catalytic protocol for the synthesis of regioselective-1,4-disubstituted-<i>1H</i> -1,2,3-triazoles at room temperature
  作者：Manashjyoti Konwar、Roktopol Hazarika、Abdul A. Ali、Mitali Chetia、Nageshwar D. Khupse、Prakash J. Saikia、Diganta Sarma

  DOI：10.1002/aoc.4425

  日期：2018.8

  A novel and highly efficient method for the synthesis of 1,4‐disubstituted‐1H‐1,2,3‐triazoles by copper‐catalyzed azide‐alkyne cycloaddition has been developed. This economic and sustainable protocol uses a readily available Benedict's solution/Vitamin C catalyst system affording a wide range of 1,4‐disubstituted‐1H‐1,2,3‐triazoles under mild conditions.

  通过铜催化的叠氮化物-炔烃环加成反应，已开发出一种新颖且高效的合成1,4-二取代-1H -1,1,2,3-三唑的方法。这种经济且可持续的方案使用易于使用的本尼迪克特溶液/维生素C催化剂体系，在温和的条件下可提供多种1,4-二取代-1H -1,1,2,3-三唑。
• (DHQD)₂PHAL ligand-accelerated Cu-catalyzed azide–alkyne cycloaddition reactions in water at room temperature
  作者：Abdul Aziz Ali、Mitali Chetia、Prakash J. Saikia、Diganta Sarma

  DOI：10.1039/c4ra12572j

  日期：——

  Herein, we have described, a ‘Click Chemistry’ protocol for the rapid synthesis of 1,2,3-triazoles in water. (DHQD)2PHAL has been found to be an excellent accelerating ligand for the copper(I)-catalyzed azide–alkyne cycloaddition reaction under air. The procedure is simple, efficient, environmentally-friendly and the products were isolated in excellent yields with high purity.

  在这里，我们已经描述了一种“点击化学”方案，用于在水中快速合成1,2,3-三唑。（DHQD）2 PHAL是铜（I）在空气中催化的叠氮化物-炔烃环加成反应的极佳促进配体。该过程简单，高效，环保，并且以高收率和高纯度分离出了产品。
• Facile route for the regioselective synthesis of 1,4-disubstituted 1,2,3-triazole using copper nanoparticles supported on nanocellulose as recyclable heterogeneous catalyst
  作者：Mitali Chetia、Abdul A Ali、Ankur Bordoloi、Diganta Sarma

  DOI：10.1007/s12039-017-1318-y

  日期：2017.8

  AbstractIn this work, a green and efficient methodology has been developed for the synthesis of 1,2,3-triazoles by ‘copper nanoparticles supported on nanocellulose (CuNPs/NC)-catalyzed azide-alkyne cycloaddition reaction in glycerol, an environmentally benign solvent, with excellent yields. The present catalyst was characterized by TEM, XRD, SEM-EDX and FT-IR spectroscopy. The reusability of the prepared

  摘要在这项工作中，开发了一种绿色高效的方法，可通过在环保的溶剂甘油中，纳米纤维素（CuNPs / NC）催化的叠氮化物-炔烃环加成反应上负载的铜纳米颗粒合成1,2,3-三唑。产量极高。通过TEM，XRD，SEM-EDX和FT-IR光谱对本催化剂进行表征。对制得的纳米催化剂的可重复使用性进行了多达五次的检查，而催化活性没有明显损失。 图形概要： 概要：制备了负载在高度结晶的纳米纤维素上的铜纳米颗粒催化剂，该催化剂可有效地用于由各种叠氮化物和炔烃的1,3-偶极环加成反应而重要的区域选择性合成1,4-二取代的1,2,3-三唑。
• AgN(CN)2/DIPEA/H2O-EG: a highly efficient catalytic system for synthesis of 1,4-disubstituted-1,2,3 triazoles at room temperature
  作者：Abdul Aziz Ali、Mitali Chetia、Bishwajit Saikia、Prakash J. Saikia、Diganta Sarma

  DOI：10.1016/j.tetlet.2015.09.025

  日期：2015.10

  A novel, efficient and robust method for silver-catalyzed azide-alkyne cycloaddition (AgAAC) reactions in H2O/Ethylene glycol (EG) at room temperature has been developed. The protocol addresses silver dicyanamide/DIPEA as a highly effective catalyst system for the regioselective formation of 1,4-disubstituted-1,2,3 triazoles under mild conditions. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis and Structure−Activity Relationships of 1-Phenyl-1<i>H</i>-1,2,3-triazoles as Selective Insect GABA Receptor Antagonists
  作者：Mohammad Sayed Alam、Ryu Kajiki、Hiromi Hanatani、Xiangyu Kong、Fumiyo Ozoe、Yoshihisa Matsui、Fumio Matsumura、Yoshihisa Ozoe

  DOI：10.1021/jf052773i

  日期：2006.2.1

  To study the interaction of phenylheterocycles with gamma-aminobutyric acid (GABA) receptors, 4- or 5-alkyl(or phenyl)-1-phenyl-1 H-1,2,3-triazoles were synthesized and examined for their ability to inhibit the specific binding of [H-3]-4'-ethynyl-4-n-propylbicycloorthobenzoate (EBOB), a noncompetitive antagonist, to the housefly and rat GABA receptors, as well as to the beta 3 subunit homo-oligomer of the human GABA receptor investigated as a model receptor. 4-Substituted 1-phenyl-1 H-1,2,3-triazoles were found to be more potent competitive inhibitors than the 5-substituted regioisomers in the case of all receptors. The 4-tert-butyl or 4-n-propyl analogue of 1-(2,6-dichloro-4-trifluoromethylphenyl)1 H-1,2,3-triazole exhibited the highest level of inhibition of [H-3]EBOB binding to all receptors. Most of the synthesized analogues were more active in terms of the inhibition of EBOB binding to the housefly and human beta 3 GABA receptors than to the rat receptor. The 4-cyclohexyl analogue showed the highest (185-fold) housefly versus rat receptor selectivity. A three-dimensional quantitative structure-activity relationship (3D-QSAR) analysis demonstrated that both the 4-trifluoromethyl-2,6dichloro substitution on the phenyl ring and a small, bulky, hydrophobic substituent at the 4-position of the triazole ring played significant roles in conferring high potency in cases involving the housefly and human beta 3 receptors. The human beta 3 receptor resembled the housefly receptor in terms of their recognition of phenyltriazoles, whereas 3D-QSAR analysis revealed a slight difference between the two receptors in terms of their mechanisms of recognition of the para-substituent on the phenyl moiety. Some of the triazoles synthesized here exhibited insecticidal activity, which was correlated with their ability to inhibit [H-3]EBOB binding to the housefly receptor. Thus, 1-phenyl-1 H-1,2,3-triazoles with the appropriate substituents exert insecticidal activity by selectively acting at the site for noncompetitive antagonism of insect GABA receptors.