1-benzyl-4-(4-chlorobutyl)-1H-1,2,3-triazole

• 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-benzyl-4-(4-chlorobutyl)-1H-1,2,3-triazole
• 英文别名: 1-Benzyl-4-(4-chlorobutyl)triazole
• 化学式: C₁₃H₁₆ClN₃
• 分子量: 249.743
• InChiKey: PIIGWTNTNUZZRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 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-(4-chlorobutyl)-1H-1,2,3-triazole 、 bis(trifluoromethane)sulfonimide lithium 在 potassium iodide 作用下， 以 乙腈 、 水 为溶剂， 以62%的产率得到
  参考文献：
  名称：

  Oxidative Esterification of Aldehydes Using Mesoionic 1,2,3-Triazolyl Carbene Organocatalysts

  摘要：

  The synthesis and catalytic activity of a new class of 1,2,3-triazolyl N-heterocyclic carbene organocatalysts is described. These new catalysts chemoselectively facilitate the oxidative esterification of aldehydes. NMR acidity studies show an inverse correlation between triazolium acidity and reactivity. Kinetic studies show that the resting state of the catalyst involves a NHC-aldehyde adduct. A catalytically active intermediate was synthesized and characterized by X-ray diffraction as the initial carbene aldehyde adduct

  DOI：

  10.1021/ol501458p
• 作为产物：
  描述：

  溴甲苯 在 sodium azide 、 copper diacetate 、 N,N-二异丙基乙胺 作用下， 以 水 、 丙酮 、 乙腈 为溶剂， 反应 1.0h， 生成 1-benzyl-4-(4-chlorobutyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  Oxidative Esterification of Aldehydes Using Mesoionic 1,2,3-Triazolyl Carbene Organocatalysts

  摘要：

  The synthesis and catalytic activity of a new class of 1,2,3-triazolyl N-heterocyclic carbene organocatalysts is described. These new catalysts chemoselectively facilitate the oxidative esterification of aldehydes. NMR acidity studies show an inverse correlation between triazolium acidity and reactivity. Kinetic studies show that the resting state of the catalyst involves a NHC-aldehyde adduct. A catalytically active intermediate was synthesized and characterized by X-ray diffraction as the initial carbene aldehyde adduct

  DOI：

  10.1021/ol501458p

文献信息

• Click chemistry promoted by graphene supported copper nanomaterials
  作者：Ali Shaygan Nia、Sravendra Rana、Diana Döhler、Xavier Noirfalise、Alice Belfiore、Wolfgang H. Binder

  DOI：10.1039/c4cc07774a

  日期：——

  A facile and robust approach is provided for the synthesis of highly dispersed copper nanoparticles immobilized onto graphene nanosheets, useful as a recyclable and reusable heterogeneous catalyst with excellent catalytic activity to achieve Cu(I)-catalyzed [3+2] cycloaddition 'click' chemistry.

  提供了一种简便且稳健的方法来合成固定在石墨烯纳米片上的高度分散的铜纳米颗粒，可用作具有可催化活性的可回收和可重复使用的非均相催化剂，以实现Cu（I）催化的[3 + 2]环加成“点击”化学反应。
• Nickel-Catalyzed Azide–Alkyne Cycloaddition To Access 1,5-Disubstituted 1,2,3-Triazoles in Air and Water
  作者：Woo Gyum Kim、Mi Eun Kang、Jae Bin Lee、Min Ho Jeon、Sungmin Lee、Jungha Lee、Bongseo Choi、Pedro M. S. D. Cal、Sebyung Kang、Jung-Min Kee、Gonçalo J. L. Bernardes、Jan-Uwe Rohde、Wonyoung Choe、Sung You Hong

  DOI：10.1021/jacs.7b06338

  日期：2017.9.6

  Herein, we report a method to access 1,5-disubstituted 1,2,3-triazoles using a Cp2Ni/Xantphos catalytic system. The reaction proceeds both in water and organic solvents at room temperature. This protocol is simple and scalable with a broad substrate scope including both aliphatic and aromatic substrates. Moreover, triazoles attached with carbohydrates or amino acids are prepared via this cycloaddition

  过渡金属催化或无金属的叠氮化物-炔烃环加成是获得1,4-或1,5-二取代的1,2,3-三唑的方法。尽管通过铜催化的环加成反应获得1，4-二取代产物已应用于生物分子反应系统，但由于底物范围有限，在水和环境条件下，叠氮化物-炔烃的环加成反应仍可用于获得互补的1,5-区域异构体。对湿气/空气敏感的催化剂。在这里，我们报告一种使用Cp 2访问1,5-二取代1,2,3-三唑的方法Ni / Xantphos催化系统。反应在室温下在水和有机溶剂中进行。该协议是简单且可扩展的，具有广泛的底物范围，包括脂肪族和芳香族底物。此外，通过该环加成反应制备了与碳水化合物或氨基酸连接的三唑。
• Carbon-Supported Copper Nanomaterials: Recyclable Catalysts for Huisgen [3+2] Cycloaddition Reactions
  作者：Ali Shaygan Nia、Sravendra Rana、Diana Döhler、Franz Jirsa、Annette Meister、Liberata Guadagno、Eik Koslowski、Michael Bron、Wolfgang H. Binder

  DOI：10.1002/chem.201501217

  日期：2015.7.20

  graphene/carbon nanotubes) were prepared and used as a recyclable and reusable catalyst to achieve CuI‐catalyzed [3+2] cycloaddition click chemistry. Carbon nanomaterials with immobilized N‐heterocyclic carbene (NHC)‐Cu complexes prepared from an imidazolium‐based carbene and CuI show excellent stability including high efficiency at low catalyst loading. The catalytic performance evaluated in solution and in bulk

  制备了固定在碳纳米材料（CNM；石墨烯/碳纳米管）上的高度分散的铜纳米颗粒，并将其用作可回收和可重复使用的催化剂，以实现Cu I催化的[3 + 2]环加成点击化学反应。由咪唑基卡宾和Cu I制备的具有固定N杂环卡宾（NHC）-Cu配合物的碳纳米材料显示出优异的稳定性，包括在低催化剂负载下的高效率。在溶液和本体中评估的催化性能表明，两种类型的Cu-CNM均可作为点击反应的有效可循环催化剂（超过10个循环），而不会分解和使用外部添加剂。
• Heterogeneous Copper-in-Charcoal-Catalyzed Click Chemistry
  作者：Bruce H. Lipshutz、Benjamin R. Taft

  DOI：10.1002/anie.200603726

  日期：2006.12.11
• A Highly Active Catalyst for Huisgen 1,3-Dipolar Cycloadditions Based on the Tris(triazolyl)methanol−Cu(I) Structure
  作者：Salih Özçubukçu、Erhan Ozkal、Ciril Jimeno、Miquel A. Pericàs

  DOI：10.1021/ol9018776

  日期：2009.10.15

  A new tris(1-benzyl-1H-1,2,3-triazol-4-yl)methanol ligand 3 has been prepared by a triple Cu(I)-catalyzed alkyne-azide 1,3-dipolar cycloaddition (CuAAC). Ligand 3 forms a stable complex with CuCl, which catalyzes the Huisgen 1,3-dipolar cycloaddition on water or under neat conditions. Low catalyst loadings, short reaction times at room temperature, and compatibility with free amino groups make 3-CuCl an outstanding catalyst for CuAAC.