1-benzyl-4-(2-bromoethyl)-1H-1,2,3-triazole | 1250525-60-0

• 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-(2-bromoethyl)-1H-1,2,3-triazole
• 英文别名: 1-Benzyl-4-(2-bromoethyl)triazole
• CAS: 1250525-60-0
• 化学式: C₁₁H₁₂BrN₃
• 分子量: 266.14
• InChiKey: AMEKZPLKZGKJFD-UHFFFAOYSA-N

物化性质

• 熔点：
  78-79 °C(Solv: ethyl acetate (141-78-6); ligroine (8032-32-4))
• 沸点：
  392.9±44.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 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-(2-bromoethyl)-1H-1,2,3-triazole 在 sodium azide 、 copper(II) acetate monohydrate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 1-[2-(1-benzyl-1H-1,2,3-triazol-4-yl)ethyl]-4-[2-(4-phenyl-1H-1,2,3-triazol-1-yl)ethyl]-1H-1,2,3-triazole
  参考文献：
  名称：

  A facile synthesis of N–C linked 1,2,3-triazole-oligomers

  摘要：

  The synthesis of the title oligomers was performed by means of an iterative sequence of 1,3-dipolar cycloaddition reactions of appropriate azides, starting from commercial 4-bromo-1-butyne as a key intermediate. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.040
• 作为产物：
  描述：

  溴甲苯 在 sodium azide 、 [5-(3-butylimidazol-2-yliden-1-yl)-25,26,27,28-tetrapropyloxycalix[4]arene]copper bromide 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 生成 1-benzyl-4-(2-bromoethyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  带有NHC–杯芳烃单元的铜络合物：点击化学的合成与应用†

  摘要：

  报道了杯[4]芳烃负载的N-杂环卡宾（NHC）铜配合物的合成。通过常规程序制备单取代的杯[4]芳烃，然后连接咪唑基以产生NHC配体的前体。用两个烷​​基溴化物进行烷基化，然后进行金属化，得到了特征充分的原始配合物。X射线结构显示出铜的“外”构象。在点击化学中研究了配合物的催化活性，并显示出良好的性能。特别是，在无溶剂条件下和快速的反应时间下，高收率合成了三种新的三唑。测试了新合成的手性配合物的消旋叠氮化物的动力学拆分。

  DOI：

  10.1039/c6nj02089e

文献信息

• Key Non-Metal Ingredients for Cu-catalyzed “Click” Reactions in Glycerol: Nanoparticles as Efficient Forwarders
  作者：Marta Rodríguez-Rodríguez、Patricia Llanes、Christian Pradel、Miquel A. Pericàs、Montserrat Gómez

  DOI：10.1002/chem.201604048

  日期：2016.12.12

  The effect of long‐alkyl‐chain amines in CuI‐assisted azide–alkyne cycloadditions of terminal alkynes with organic azides in glycerol and other environmentally benign solvents (water, ethanol) has been examined. The presence of these additives favors the in situ formation of CuI‐based nanoparticles and results in an increase of the catalytic reactivity. In glycerol, liquid‐phase transmission electron

  考察了长烷基链胺在末端炔烃的CuI辅助的叠氮化物-炔烃环加成反应中与甘油和其他环境友好溶剂（水，乙醇）中的有机叠氮化物的作用。这些添加剂的存在有利于Cu I基纳米颗粒的原位形成，并导致催化反应性的提高。在甘油中，由于该溶剂的蒸气压可忽略，因此液相透射电子显微镜（TEM）分析证明，Cu I纳米颗粒负责观察到的催化活性。已经研究了多种炔烃和叠氮化物（14种组合），证实了这些添加剂在铜催化的惠斯根环加成中的作用。
• 반응용매에 대한 혼화성 차이를 이용한 화학선택적 트리아졸의 제조방법
  申请人：AGENCY FOR DEFENSE DEVELOPMENT 국방과학연구소(319980058262) BRN ▼314-83-03869

  公开号：KR102147971B1

  公开（公告）日：2020-08-25

  본 발명은, 반응용매에 대한 혼화성 차이를 이용한 화학선택적 트리아졸의 제조방법에 관한 것으로, 보다 구체적으로, 반응 용매에 대한 혼화성이 상이한 2종 이상의 알킨 화합물; 또는 반응 용매에 대한 혼화성이 상이한 2종 이상의 아지드 화합물;을 주원료로 하고, 이들의 반응 용매에 대한 혼화성 차이를 이용한, 화학선택적 아지드-알킨 고리첨가 반응(Chemoselective cycloaddition reaction)을 진행하는 단계; 및 고리첨가 반응 이후에 후처리를 통해 1,4-이치환-1,2,3-트리아졸 화합물을 획득하는 단계; 를 포함하는, 화학선택적 트리아졸의 제조방법에 관한 것이다.

  这项发明涉及利用溶剂混合物中的混合性差异制备三唑化合物的化学选择性方法，更具体地说，该方法以两种或两种以上的烯烃化合物，其在反应溶剂中的混合性不同，或两种或两种以上的亚胺化合物，其在反应溶剂中的混合性不同，作为原料，并利用它们在反应溶剂中的混合性差异，进行化学选择性的亚胺-烯烃环加成反应，然后通过后处理步骤获得1,4-二取代-1,2,3-三唑化合物，该方法涉及到制备化学选择性三唑的方法。
• Glycerol: a biorenewable solvent for base-free Cu(i)-catalyzed 1,3-dipolar cycloaddition of azides with terminal and 1-iodoalkynes. Highly efficient transformations and catalyst recycling
  作者：Cristian Vidal、Joaquín García-Álvarez

  DOI：10.1039/c4gc00451e

  日期：——

  The combination of CuI and glycerol exhibits a versatile and high catalytic activity in the Huisgen cycloaddition of azides and terminal or 1-iodoalkynes under standard bench experimental conditions (room temperature, under air and in the absence of a base) providing a pivotal contribution to Green Chemistry. Since the catalytic reaction: (i) is amenable at low catalyst loading and accessible on a high scale; (ii) tolerates a variety of functionalities (including the presence of a free thio moiety in the substrate); (iii) can be effectively recycled (up to 6 consecutive runs); and (iv) is isolated in a straightforward manner (by simple filtration in the absence of organic solvents at any stage of the synthesis), the practical application of this methodology provides a complementary synthetic tool to the familiar CuAAC reactions.

  在标准实验条件下（室温、空气和无碱条件下），CuI 和甘油的组合在叠氮化物和末端或 1-iodo 烷炔的 Huisgen 环加成反应中表现出多功能和高催化活性，为绿色化学做出了重要贡献。由于该催化反应：(i) 适合于低催化剂负载和大规模使用；(ii) 可容忍多种官能团（包括底物中存在游离硫代分子）；(iii) 可有效循环使用（最多连续运行 6 次）；(iv) 可直接分离（在合成的任何阶段均不使用有机溶剂的情况下通过简单过滤），因此该方法的实际应用为我们熟悉的 CuAAC 反应提供了一种补充合成工具。
• Copper(II) SBA-15: A reusable catalyst for azide–alkyne cycloaddition
  作者：Ibtissem Jlalia、Florian Gallier、Nancy Brodie-Linder、Jacques Uziel、Jacques Augé、Nadège Lubin-Germain

  DOI：10.1016/j.molcata.2014.06.003

  日期：2014.11

  The azide-alkyne cycloaddition reaction was investigated under catalytic conditions involving a copper(II) loaded silica based mesoporous material. Cu(II) SBA-15 demonstrated a high catalytic effect in 1,4-triazoles synthesis in organic. No additives such as a base or a reductant are required. Quantitative yields were obtained and a mere filtration of the mesoporous material which retains copper(II) allows the recovery of the catalyst. In addition, up to 5 times recycling of the catalyst was achieved without loss of the activity affording 1,4-triazoles in a yield up to 98%. (C) 2014 Elsevier B.V. All rights reserved.
• Huisgen click cycloadditions from a copper(II)-tren precatalyst without external sacrificial reductant
  作者：Lydie Harmand、Marie-Hélène Lescure、Nicolas Candelon、Mathieu Duttine、Dominique Lastécouères、Jean-Marc Vincent

  DOI：10.1016/j.tetlet.2012.01.035

  日期：2012.3

  The copper(II) complex [Cu(C18(6)tren)](Br)(2), 2, is an efficient precatalyst for the Huisgen 'click' cycloaddtion which can be used at low loading without the requirement of an external sacrificial reductant such as sodium ascorbate. EPR studies support the in situ reduction of 2 by the alkyne to generate a reactive copper(1) catalyst. (C) 2012 Elsevier Ltd. All rights reserved.