1-benzyl-4,5-diethyl-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-4,5-diethyl-1H-1,2,3-triazole
• 英文别名: 1-Benzyl-4,5-diethyltriazole
• 化学式: C₁₃H₁₇N₃
• 分子量: 215.298
• InChiKey: VSZHOSYAWYKVBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  3-己炔 、 苄基叠氮 在 [Cu(tris(2-dioctadecylaminoethyl)amine)]Br 作用下， 以 正辛烷 为溶剂， 反应 24.0h， 以85%的产率得到1-benzyl-4,5-diethyl-1H-1,2,3-triazole
  参考文献：
  名称：

  一种高活性和可重复使用的铜（I）-催化剂，用于叠氮化物和炔烃的“咔哒” 1,3-偶极环加成反应。

  摘要：

  铜（I）络合物[Cu（C18（6）tren）] Br 1（C18（6）tren =三（2-二十八烷基氨基乙基）胺）在有氧条件下表现出良好的稳定性，是一种多功能，高反应性和可回收的催化剂用于末端或内部炔烃与叠氮化物的惠斯根环加成反应，是制备“点击”树枝状聚合物的有用催化剂。

  DOI：

  10.1039/b716306a

文献信息

• (NHC)Copper(I)-Catalyzed [3+2] Cycloaddition of Azides and Mono- or Disubstituted Alkynes
  作者：Silvia Díez-González、Andrea Correa、Luigi Cavallo、Steven P. Nolan

  DOI：10.1002/chem.200600961

  日期：2006.10.5

  A versatile and highly efficient catalyst for the Huisgen cycloaddition reaction has been developed. Previously isolated or in situ generated azides yielded 1,2,3-triazoles with differently substituted alkynes in the presence of a [(NHC)CuBr] complex (NHC = N-heterocyclic carbene). Extremely high reaction rates and excellent yields were obtained in all cases. This catalytic system fulfils the requirements

  已经开发了用于Huisgen环加成反应的通用且高效的催化剂。在[（NHC）CuBr]配合物（NHC = N-杂环卡宾）存在下，先前分离或原位生成的叠氮化物可生成带有不同取代炔烃的1,2,3-三唑。在所有情况下均获得了极高的反应速度和极好的收率。该催化系统以其温和且方便的条件满足“点击化学”的要求，特别是在无水或无溶剂的反应中，并且无需纯化步骤即可进行简单分离。此外，首次将内部炔烃成功用于该铜催化的环加成反应中。在该特定系统上的DFT计算为双取代炔烃提出了新的机理途径。
• CYCLOADDITION OF AZIDES AND ALKYNES
  申请人：Nolan Steven P.

  公开号：US20090069569A1

  公开（公告）日：2009-03-12

  This invention provides a process which comprises contacting, in a reaction zone, at least one organic azide, at least one alkyne, and at least one N-heterocyclic carbene copper compound in which the ligands are either (i) a halide and an N-heterocyclic carbene or (ii) two N-heterocyclic carbenes and a BF 4 − or PF 6 − anion, to form a 1,2,3-triazole in which at least the 1 and 4 positions each has a substituent. The N-heterocyclic carbene either an imidazol-2-ylidene in which the 1 and the 3 positions each has a substituent which has at least one carbon atom, or a 4,5-dihydro-imidazol-2-ylidene in which the 1 and the 3 positions each has a substituent which has at least one carbon atom.

  这项发明提供了一种方法，其中包括在反应区域中接触至少一种有机叠氮化合物、至少一种炔烃以及至少一种N-杂环卡宾铜化合物，其中配体可以是（i）一种卤素和一种N-杂环卡宾，或者（ii）两种N-杂环卡宾和一个BF4−或PF6−阴离子，以形成一种1,2,3-三唑，其中至少1和4位置各具有一个取代基。N-杂环卡宾可以是1,3位置各具有至少一个碳原子的咪唑-2-基卡宾，或者是1,3位置各具有至少一个碳原子的4,5-二氢咪唑-2-基卡宾。
• A highly active and reusable copper(<scp>i</scp>)-tren catalyst for the “click” 1,3-dipolar cycloaddition of azides and alkynes
  作者：Nicolas Candelon、Dominique Lastécouères、Abdou Khadri Diallo、Jaime Ruiz Aranzaes、Didier Astruc、Jean-Marc Vincent

  DOI：10.1039/b716306a

  日期：——

  The copper(I) complex [Cu(C18(6)tren)]Br 1 (C18(6)tren = tris(2-dioctadecylaminoethyl)amine) which exhibits a good stability towards aerobic conditions is a versatile, highly reactive and recyclable catalyst for the Huisgen cycloaddition of azides with terminal or internal alkynes and is a useful catalyst for the preparation of "click" dendrimers.

  铜（I）络合物[Cu（C18（6）tren）] Br 1（C18（6）tren =三（2-二十八烷基氨基乙基）胺）在有氧条件下表现出良好的稳定性，是一种多功能，高反应性和可回收的催化剂用于末端或内部炔烃与叠氮化物的惠斯根环加成反应，是制备“点击”树枝状聚合物的有用催化剂。
• A Study of the Scope and Regioselectivity of the Ruthenium-Catalyzed [3 + 2]-Cycloaddition of Azides with Internal Alkynes
  作者：Max M. Majireck、Steven M. Weinreb

  DOI：10.1021/jo061688m

  日期：2006.10.1

  [3 + 2]-Cycloadditions of alkyl azides with various unsymmetrical internal alkynes in the presence of Cp*RuCl(PPh3)(2) as catalyst in refluxing benzene have been examined, leading to 1,4,5-trisubstituted-1,2,3-triazoles. Whereas alkyl phenyl and dialkyl acetylenes undergo cycloadditions to afford mixtures of regioisomeric 1,2,3-triazoles, acyl-substituted internal alkynes react with complete regioselectivity. In addition, propargyl alcohols and propargyl amines were found to react with azides to afford single regioisomeric products.
• An Abnormal N-Heterocyclic Carbene-Copper(I) Complex in Click Chemistry
  作者：Samaresh Chandra Sau、Sudipta Raha Roy、Tamal K. Sen、Dinesh Mullangi、Swadhin K. Mandal

  DOI：10.1002/adsc.201300343

  日期：2013.10.11

  AbstractHerein we report the synthesis of a copper(I) chloro complex using an abnormal N‐heterocyclic carbene (aNHC) salt, 1,3‐bis(2,6‐diisopropylphenyl)‐2,4‐diphenylimidazolium. The CuCl(aNHC) complex efficiently catalyzed Huisgen 1,3‐dipolar cycloaddition reactions (click reactions) of azides with alkynes to give 1,4‐substituted 1,2,3‐triazoles in excellent yields at room temperature within short reaction time under solvent‐free conditions. The catalyst successfully activated benzyl azide and phenylacetylene under the low catalyst loading of 0.005 mol% resulting in a nearly quantitative yield of the product at room temperature with the high TON value of 19,800. The catalyst also exhibits high efficiency in the reaction between sterically hindered azides and alkynes under solvent‐free conditions at room temperature. Furthermore, a number of internal alkynes was successfully tested in this copper‐catalyzed cycloaddition reaction for synthesis of 4,5‐disubstituted triazoles.magnified image