1-(4-(1-benzyl-1H-1,2,3-triazol-4-yl)phenyl)ethanone | 1383380-46-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-(1-benzyl-1H-1,2,3-triazol-4-yl)phenyl)ethanone
• 英文别名: 1-[4-(1-Benzyltriazol-4-yl)phenyl]ethanone
• CAS: 1383380-46-8
• 化学式: C₁₇H₁₅N₃O
• 分子量: 277.326
• InChiKey: ARKQHWGXVAVEAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  47.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-碘代苯乙酮 在 5% palladium-copper on carbon 、 二乙胺 、 三苯基膦 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 1-(4-(1-benzyl-1H-1,2,3-triazol-4-yl)phenyl)ethanone
  参考文献：
  名称：

  Palladium and copper-supported on charcoal: A heterogeneous multi-task catalyst for sequential Sonogashira–Click and Click–Heck reactions

  摘要：

  This paper describes the development of one-pot sequential Sonogashira-Click and Click-Heck reactions by using Pd-Cu/C as a heterogeneous multi-task catalyst for the synthesis of heterocyclic structures. Details of the optimization studies and the substrate scope are discussed. These methodologies allow the preparation of functionalized triazoles in simple experimental conditions with inexpensive reagents. (C) 2014 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2014.01.006

文献信息

• Azide-Alkyne Cycloaddition (CuAAC) in Alkane Solvents Catalyzed by Fluorinated NHC Copper(I) Complex
  作者：Maxim A. Topchiy、Alexandra A. Ageshina、Pavel S. Gribanov、Salekh M. Masoud、Timur R. Akmalov、Sergey E. Nefedov、Sergey N. Osipov、Mikhail S. Nechaev、Andrey F. Asachenko

  DOI：10.1002/ejoc.201801538

  日期：2019.2.7

  A highly efficient and environmentally benign protocol for copper‐catalyzed alkyne–azide cycloaddition (CuAAC) in industrially important alkane solvents was developed. New (NHCF)CuI complex decorated with bulky group [(CF3)2(OiAm)C–] exhibited the best catalytic activity in the reactions of diversely substituted alkyne and azide substrates in alkane solvents.

  针对工业上重要的烷烃溶剂中的铜催化的炔-叠氮化物环加成（CuAAC），开发了一种高效且对环境无害的方案。新的（NHC F）Cu I络合物装饰有大体积基团[（CF 3）2（O i Am）C–]在烷烃溶剂中不同取代的炔烃和叠氮化物底物的反应中表现出最佳的催化活性。
• Synthesis of heterogeneous Ru(<scp>ii</scp>)-1,2,3-triazole catalyst supported over SBA-15: application to the hydrogen transfer reaction and unusual highly selective 1,4-disubstituted triazole formation <i>via</i> multicomponent click reaction
  作者：Priti Sharma、Jayant Rathod、A. P. Singh、Pradeep Kumar、Yoel Sasson

  DOI：10.1039/c7cy02619f

  日期：——

  catalyst was screened for the multicomponent click cycloaddition reaction in water medium as a green solvent and it exhibited unusual and excellent selectivity for the formation of 1,4-disubstituted triazole product under mild reaction condition. In addition, SBA-15-Tz-Ru(II)TPP catalyst also catalyzed the hydrogen transfer reaction of various carbonyl compounds with excellent catalytic activity to

  在本研究中，我们展示了一种简单有效的配体形成方法，并通过点击反应将共价锚定到异质支持物上。锚固在SBA-15的点击修饰配体上的三氯化三（三苯基膦）钌（II）络合物[RuCl 2（PPh 3）3 ]形成了一种新型的高效多相SBA-15-Tz-Ru（II）TPP催化剂。固态13 C，29 Si和31 P CP-MAS NMR光谱为形成非均相催化剂提供了证据。SBA-15-Tz-Ru（II）TPP催化剂在水介质中作为绿色溶剂进行了多组分点击环加成反应的筛选，在温和的反应条件下，它对形成1,4-二取代的三唑产物表现出不同寻常的优异选择性。此外，SBA-15-Tz-Ru（II）TPP催化剂还催化了各种具有优异催化活性的羰基化合物的氢转移反应，得到了相应的醇。非均相催化剂可以循环使用多次（五次）而不会损失反应性。
• Highly efficient click reaction on water catalyzed by a ruthenium complex
  作者：Hai Xiao Siyang、Hui Ling Liu、Xin Yan Wu、Pei Nian Liu

  DOI：10.1039/c4ra12960a

  日期：——

  The highly efficient click reaction between terminal alkynes and azides has been achieved on water using ruthenium complex RuH2(CO)(PPh3)3 as the catalyst, and the catalyst loading was decreased to 0.2 mol% on water from 5 mol% in organic solvent. The RuH2(CO)(PPh3)3/H2O system also catalyzed the one-pot click reaction of bromides, sodium azide and alkynes; in this process, azides formed in situ and

  使用钌配合物RuH 2（CO）（PPh 3）3作为催化剂，在水上实现了末端炔烃与叠氮化物之间的高效点击反应，并且在水中，催化剂的载量从5 mol％降低至0.2 mol％。溶剂。RuH 2（CO）（PPh 3）3 / H 2 O体系还催化了溴化物，叠氮化钠和炔烃的一锅法点击反应。在此过程中，叠氮化物就地形成，然后与炔烃发生点击反应。在这两种含水过程中，均以50-89％的产率获得了1,4-二取代的1,2,3-三唑，具有很高的区域选择性。
• RuH₂(CO)(PPh₃)₃ Catalyzed Selective Formation of 1,4-Disubstituted Triazoles from Cycloaddition of Alkynes and Organic Azides
  作者：Pei Nian Liu、Hai Xiao Siyang、Li Zhang、Sunny Kai San Tse、Guochen Jia

  DOI：10.1021/jo3008572

  日期：2012.7.6

  The ruthenium hydride complex RuH2(CO)(PPh3)(3) was found to be an effective catalyst for the cycloaddition reactions of terminal alkynes and azides. In the presence of RuH2(CO)(PPh3)(3), various azides reacted with a range of terminal alkynes to produce 1,4-disubstituted 1,2,3-triazoles with 100% selectivity and moderate to excellent yields.
• Palladium and copper-supported on charcoal: A heterogeneous multi-task catalyst for sequential Sonogashira–Click and Click–Heck reactions
  作者：Cybille Rossy、Jérôme Majimel、Mona Tréguer Delapierre、Eric Fouquet、François-Xavier Felpin

  DOI：10.1016/j.jorganchem.2014.01.006

  日期：2014.4

  This paper describes the development of one-pot sequential Sonogashira-Click and Click-Heck reactions by using Pd-Cu/C as a heterogeneous multi-task catalyst for the synthesis of heterocyclic structures. Details of the optimization studies and the substrate scope are discussed. These methodologies allow the preparation of functionalized triazoles in simple experimental conditions with inexpensive reagents. (C) 2014 Elsevier B. V. All rights reserved.