ethyl 2-(4-pentyl-1H-1,2,3-triazol-1-yl)acetate | 1380399-40-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 2-(4-pentyl-1H-1,2,3-triazol-1-yl)acetate
• 英文别名: Ethyl 2-(4-pentyltriazol-1-yl)acetate
• CAS: 1380399-40-5
• 化学式: C₁₁H₁₉N₃O₂
• 分子量: 225.291
• InChiKey: OUAGJALTSOTACL-UHFFFAOYSA-N

物化性质

• 沸点：
  336.3±44.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  57
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-(4-pentyl-1H-1,2,3-triazol-1-yl)acetate 在 potassium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 以96%的产率得到2-(4-n-pentyl-1H-1,2,3-triazol-1-yl)acetic acid
  参考文献：
  名称：

  Synthesis and biological evaluation of new N-acyl-homoserine-lactone analogues, based on triazole and tetrazole scaffolds, acting as LuxR-dependent quorum sensing modulators

  摘要：

  New analogues of N-acyl-homoserine-lactone (AHL), in which the amide was replaced by a triazole or tetrazole ring, were prepared and tested for their activity as LuxR-dependent QS modulators. Several compounds showed a level of antagonistic or agonistic activity, notably some 1,4-triazolic and 1,5-tetrazolic derivatives, whereas the 2,5-tetrazolic compounds were inactive. In 1,5-tetrazoles, substituted with butyrolactone and an alkyl chain, the activity was reversed, depending on the connection between the lactone and the tetrazole. The C-N connected compounds were agonists whereas the C-C connected ones were antagonists. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.06.007
• 作为产物：
  描述：

  叠氮乙酸乙酯 、 1-庚炔 在 copper(l) iodide 、 2-(4-phenyl-2H-1,2,3-triazol-2-yl)pyridine 作用下， 以 乙腈 为溶剂， 反应 1.5h， 以91%的产率得到ethyl 2-(4-pentyl-1H-1,2,3-triazol-1-yl)acetate
  参考文献：
  名称：

  吡啶基-三唑配体体系，用于高效CuI催化的叠氮化物-炔烃环加成反应

  摘要：

  吡啶基-三唑配体系统（包括N 2 -2-吡啶基1,2,3-三唑和N 1 / N 2取代的2-（NH（1,2,3-三唑-4-基）吡啶被发现是CuI催化的叠氮化物-炔烃环加成（CuAAC）反应的优良配体。催化剂负载量低，反应时间短，催化剂易于回收利用，环境温度和开瓶条件使该催化系统非常实用。碘化物阴离子可形成碘桥，与这些配体一起构建稳定的双核Cu（I）配合物，这是实现高催化活性的关键。虽然CuBr和CuCl不适合该配体系统，因为Br和Cl原子的尺寸不合适，无法形成相应的双核Cu（I）配合物。

  DOI：

  10.1016/j.catcom.2020.106165

文献信息

• Magnetic starch nanocomposite as a green heterogeneous support for immobilization of large amounts of copper ions: heterogeneous catalyst for click synthesis of 1,2,3-triazoles
  作者：Ali Pourjavadi、Anahita Motamedi、Seyed Hassan Hosseini、Mojtaba Nazari

  DOI：10.1039/c5ra25519h

  日期：——

  new magnetic heterogeneous copper catalyst was prepared by immobilization of copper ions onto a cross-linked polymeric nanocomposite composed of starch grafted polyacrylamide and functionalized Fe3O4 magnetic nanoparticles. The resulting support was loaded with large amounts of copper ions (1.6 mmol g−1). The prepared catalyst is highly active in Huisgen 1,3-dipolar cycloaddition reactions of different

  通过将铜离子固定在由淀粉接枝的聚丙烯酰胺和功能化的Fe 3 O 4磁性纳米粒子组成的交联聚合物纳米复合材料上，制备了一种新型的磁性异质铜催化剂。所得的载体上载有大量的铜离子（1.6mmol g -1）。所制备的催化剂在低催化剂量下对不同叠氮化物和炔烃的Huisgen 1,3-偶极环加成反应具有很高的活性。在温和的条件下以高收率生产了各种相应的1,2,3-三唑。该催化剂易于回收并再用于十个反应循环，没有观察到明显的催化活性损失。
• Harnessing the Dual Properties of Thiol-Grafted Cellulose Paper for Click Reactions: A Powerful Reducing Agent and Adsorbent for Cu
  作者：Jordi Rull-Barrull、Martin d'Halluin、Erwan Le Grognec、François-Xavier Felpin

  DOI：10.1002/anie.201606760

  日期：2016.10.17

  new approach exploiting the dual properties of thiol‐grafted cellulose paper for promoting copper‐catalyzed [3+2]‐cycloadditions of organic azides with alkynes and adsorbing residual copper species in solution was developed. The thiol‐grafted cellulose paper, used as a paper strip, effects the reduction of CuII to catalytically active CuI and acts as a powerful adsorbent for copper, thereby facilitating

  开发了一种新方法，该方法利用硫醇接枝纤维素纸的双重特性来促进炔烃与有机叠氮化物的铜催化[3 + 2]-环加成反应，并吸附溶液中的残留铜物种。用作纸带的硫醇接枝纤维素纸可将Cu II还原为催化活性Cu I，并作为强力的铜吸附剂，从而简化了后处理过程，并使粗混合物几乎不含铜残留物一次过滤后。
• Copper-Catalyzed Three-Component Tandem Reaction of Alkynes, α-Diazo Esters, and TMSN₃ to Access N-Substituted 1,2,3-Triazoles
  作者：Yufen Lv、Zhiwei Wang、Lianhui Song、Jindong Hao、Shuyun Zhu、Huilan Yue、Wei Wei、Dong Yi

  DOI：10.1021/acs.joc.3c02112

  日期：2023.12.15

  An efficient copper-catalyzed three-component tandem reaction of alkynes, α-diazo esters, and TMSN3 to construct triazoles has been developed. Through this strategy, a number of diverse N-substituted 1,2,3-triazoles were conveniently obtained in moderate to good yields from simple and readily available starting materials using K2CO3 as the base. The mechanism of the tandem Cu-catalyzed azide–alkyne

  开发了一种高效的铜催化炔烃、α-重氮酯和 TMSN 3的三组分串联反应来构建三唑。通过该策略，使用K 2 CO 3作为碱，从简单易得的起始原料中以中等至良好的收率方便地获得了多种不同的N-取代1,2,3-三唑。研究了串联铜催化叠氮化物-炔烃环加成（CuAAC）和铜类碳烯参与的 C-N 偶联反应的机理。
• Pyridinyl-triazole ligand systems for highly efficient CuI-catalyzed azide-alkyne cycloaddition
  作者：Lei Zheng、Ye Wang、Xianggao Meng、Yunfeng Chen

  DOI：10.1016/j.catcom.2020.106165

  日期：2021.1

  N1/N2-substituted 2-(NH-1,2,3-triazol-4-yl)pyridines) were found to be superior ligands for CuI-catalyzed azide-alkyne cycloaddition (CuAAC) reactions. Low catalyst loadings, short reaction times, facile catalyst recyclability, ambient temperature, and open-flask conditions made this catalytic system very practical. The iodide anions could form iodine bridges to construct stable dinuclear Cu(I) complexes with these

  吡啶基-三唑配体系统（包括N 2 -2-吡啶基1,2,3-三唑和N 1 / N 2取代的2-（NH（1,2,3-三唑-4-基）吡啶被发现是CuI催化的叠氮化物-炔烃环加成（CuAAC）反应的优良配体。催化剂负载量低，反应时间短，催化剂易于回收利用，环境温度和开瓶条件使该催化系统非常实用。碘化物阴离子可形成碘桥，与这些配体一起构建稳定的双核Cu（I）配合物，这是实现高催化活性的关键。虽然CuBr和CuCl不适合该配体系统，因为Br和Cl原子的尺寸不合适，无法形成相应的双核Cu（I）配合物。
• Synthesis and biological evaluation of new N-acyl-homoserine-lactone analogues, based on triazole and tetrazole scaffolds, acting as LuxR-dependent quorum sensing modulators
  作者：Mohamad Sabbah、Fanny Fontaine、Lucie Grand、Mohamed Boukraa、Mohamed L. Efrit、Alain Doutheau、Laurent Soulère、Yves Queneau

  DOI：10.1016/j.bmc.2012.06.007

  日期：2012.8

  New analogues of N-acyl-homoserine-lactone (AHL), in which the amide was replaced by a triazole or tetrazole ring, were prepared and tested for their activity as LuxR-dependent QS modulators. Several compounds showed a level of antagonistic or agonistic activity, notably some 1,4-triazolic and 1,5-tetrazolic derivatives, whereas the 2,5-tetrazolic compounds were inactive. In 1,5-tetrazoles, substituted with butyrolactone and an alkyl chain, the activity was reversed, depending on the connection between the lactone and the tetrazole. The C-N connected compounds were agonists whereas the C-C connected ones were antagonists. (C) 2012 Elsevier Ltd. All rights reserved.