1,4-dihexyl-1,2,3-triazole | 936475-46-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,4-dihexyl-1,2,3-triazole
• 英文别名: 1,4-Dihexyl-1,2,3-triazole；1,4-dihexyltriazole
• CAS: 936475-46-6
• 化学式: C₁₄H₂₇N₃
• 分子量: 237.388
• InChiKey: LDENVAIVIQFYPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  17
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  1,4-dihexyl-1,2,3-triazole 以 二氯甲烷 、 乙腈 为溶剂， 反应 53.0h， 生成
  参考文献：
  名称：

  Wingtip substituents tailor the catalytic activity of ruthenium triazolylidene complexes in base-free alcohol oxidation

  摘要：

  一系列包含不同芳基和烷基侧翼基团的1,2,3-三唑啉二烯配体的RuII（η6-芳烃）配合物已通过NMR光谱、微量分析以及在一种情况下的X射线衍射得以制备和表征。所有配合物均是活性的醇氧化为相应醛/酮的催化剂前体，无需添加氧化剂或碱。侧翼基团对催化活性有直接影响，烷基侧翼基团提供最活跃的物种，而芳基侧翼基团导致较低的活性。氮键合的苯基是抑制性最强的侧翼基团，因为环金属化作用。观察到芳烃解离作为潜在的催化剂失活途径。

  DOI：

  10.1039/c3dt32939a
• 作为产物：
  描述：

  溴己烷 在 sodium azide 、 三[(1-苄基-1H-1,2,3-三唑-4-基)甲基]胺 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.33h， 生成 1,4-dihexyl-1,2,3-triazole
  参考文献：
  名称：

  A Triazolium‐Anchored Self‐Immolative Linker Enables Self‐Assembly‐Driven siRNA Binding and Esterase‐Induced Release

  摘要：

  AbstractThe increased importance of RNA‐based therapeutics comes with a need to develop next‐generation stimuli‐responsive systems capable of binding, transporting and releasing RNA oligomers. In this work, we describe triazolium‐based amphiphiles capable of siRNA binding and enzyme‐responsive release of the nucleic acid payload. In aqueous medium, the amphiphile self‐assembles into nanocarriers that can disintegrate upon the addition of esterase. Key to the molecular design is a self‐immolative linker that is anchored to the triazolium moiety and acts as a positively‐charged polar head group. We demonstrate that addition of esterase leads to a degradation cascade of the linker, leaving the neutral triazole compound unable to form complexes and therefore releasing the negatively‐charged siRNA. The reported molecular design and overall approach may have broad utility beyond this proof‐of‐principle study, because the underlying CuAAC “click” chemistry allows bringing together three groups very efficiently as well as cleaving off one of the three groups under the mild action of an esterase enzyme.

  DOI：

  10.1002/chem.202203311

文献信息

• “Click” 1,2,3-triazoles as tunable ligands for late transition metal complexes
  作者：Bart M. J. M. Suijkerbuijk、Bas N. H. Aerts、Harm P. Dijkstra、Martin Lutz、Anthony L. Spek、Gerard van Koten、Robertus J. M. Klein Gebbink

  DOI：10.1039/b701978p

  日期：——

  The potential of “click” 1,2,3-triazoles to act as mono-dentate ligands in late transition metal complexes is explored relative to other commonly-used Lewis bases and it is shown that their coordination strength, determined by their 1- and 4-substituents, is easily tunable.

  探讨了“点击”1,2,3-三唑作为过渡金属复杂物中单齿配体的潜力，并与其他常用的路易斯碱进行比较，结果表明其配位强度由其位于1位和4位的取代基决定，并且可以轻松调节。
• A One-Pot Synthesis of Constitutionally Unsymmetrical Rotaxanes Using Sequential CuI-Catalyzed Azide–Alkyne Cycloadditions
  作者：Jason M. Spruell、William R. Dichtel、James R. Heath、J. Fraser Stoddart

  DOI：10.1002/chem.200800067

  日期：2008.5.9

  A one-pot sequential Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) strategy is presented for the synthesis of constitutionally unsymmetrical cyclobis(paraquat-p-phenylene)-based rotaxanes in good yields from simple starting materials. The methodology consists of performing multiple CuAAC reactions to stopper a pseudorotaxane in a stepwise manner, the order of which is controlled through silyl-protection

  提出了一锅顺序Cu（I）催化的叠氮化物-炔烃环加成（CuAAC）策略，用于从简单的起始原料以高收率合成结构不对称的基于环双（百草枯-对苯撑）的轮烷。该方法包括逐步进行多个CuAAC反应以终止假轮烷，其顺序通过末端炔基的甲硅烷基保护和Ag（I）催化的脱保护作用来控制。两亲性支链[4]轮烷的合成突出了该方法。该方法提高了访问越来越复杂的机械互锁化合物以在设备中用作复杂和功能性分子机械的能力。
• Direct Synthesis of Mesoionic Carbene (MIC)-Stabilized Gold Nanoparticles from 1,2,3-Triazolium Salts
  作者：Alexandre Porcheron、Omar Sadek、Salem Ba Sowid、Nathalie Bridonneau、Laura Hippolyte、Dimitri Mercier、Philippe Marcus、Lukmonjon Mutalliev、Clément Chauvier、Corinne Chanéac、Louis Fensterbank、François Ribot

  DOI：10.1021/acs.chemmater.3c01162

  日期：2023.9.12

  through the use of thiols and imidazolylidene N-heterocyclic carbene-capping ligands. Herein, we report that mesoionic carbene (MIC) ligands, based on the 1,2,3-triazol-5-ylidene scaffold, allow the expeditive preparation of AuNPs of very high stability through a simple and straightforward one-pot protocol directly from triazolium salts and separated Au(III) sources. Control over the size of AuNPs has

  过去几年，金纳米粒子 (AuNP) 的稳定化和功能化方面取得了重大成就，主要是通过使用硫醇和咪唑基 N-杂环卡宾封端配体。在此，我们报道了基于 1,2,3-三唑-5-亚基支架的介离子卡宾 (MIC) 配体，可以通过简单直接的一锅法直接从三唑快速制备具有非常高稳定性的 AuNP盐和分离的 Au(III) 源。通过改变 Au/配体比例以及三唑鎓盐的性质可以控制 AuNP 的尺寸，通过点击化学轻松合成 MIC 前体有利于后者。13这些 MIC-AuNP 的表征13C固态(ss) NMR和X射线光电子能谱(XPS)暗示仅包含Au(0)的纳米粒子表面上仅存在MIC。
• Heterogeneous Catalysis through Microcontact Printing
  作者：Jason M. Spruell、Bonnie A. Sheriff、Dorota I. Rozkiewicz、William R. Dichtel、Rosemary D. Rohde、David N. Reinhoudt、J. Fraser Stoddart、James R. Heath

  DOI：10.1002/anie.200803480

  日期：2008.12.8
• Wingtip substituents tailor the catalytic activity of ruthenium triazolylidene complexes in base-free alcohol oxidation
  作者：Daniel Canseco-Gonzalez、Martin Albrecht

  DOI：10.1039/c3dt32939a

  日期：——

  A series of RuII (η6-arene) complexes with 1,2,3-triazolylidene ligands comprising different aryl and alkyl wingtip groups have been prepared and characterized by NMR spectroscopy, microanalysis, and in one case by X-ray diffraction. All complexes are active catalyst precursors for the oxidation of alcohols to the corresponding aldehydes/ketones without the need of an oxidant or base as additive. The wingtip groups have a direct impact on the catalytic activity, alkyl wingtips providing the most active species while aryl wingtip groups induce lower activity. An N-bound phenyl group was the most inhibiting wingtip group due to cyclometalation. Arene dissociation was observed as a potential catalyst deactivation pathway.

  一系列包含不同芳基和烷基侧翼基团的1,2,3-三唑啉二烯配体的RuII（η6-芳烃）配合物已通过NMR光谱、微量分析以及在一种情况下的X射线衍射得以制备和表征。所有配合物均是活性的醇氧化为相应醛/酮的催化剂前体，无需添加氧化剂或碱。侧翼基团对催化活性有直接影响，烷基侧翼基团提供最活跃的物种，而芳基侧翼基团导致较低的活性。氮键合的苯基是抑制性最强的侧翼基团，因为环金属化作用。观察到芳烃解离作为潜在的催化剂失活途径。