1-octyl-4-phenyl-1H-[1,2,3]triazole | 853052-50-3

• 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-octyl-4-phenyl-1H-[1,2,3]triazole
• 英文别名: 1-octyl-4-phenyl-1,2,3-triazole；1-Octyl-4-phenyl-1H-1,2,3-triazole；1-octyl-4-phenyltriazole
• CAS: 853052-50-3
• 化学式: C₁₆H₂₃N₃
• 分子量: 257.379
• InChiKey: FOGPNMHCDUQVGH-UHFFFAOYSA-N

物化性质

• 熔点：
  78-79 °C
• 沸点：
  403.2±38.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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-octyl-4-phenyl-1H-[1,2,3]triazole 在 lithium diisopropyl amide 、 重水 作用下， 以 四氢呋喃 为溶剂， 生成 1-octyl-4-phenyl-1H-1,2,3-triazole-5-d₁
  参考文献：
  名称：

  Lithiation‐Functionalisation of Triazoles Bearing Electron‐Withdrawing N ‐Substituents: Challenges and Solutions**

  摘要：

  AbstractThe regioselective lithiation of 1,2,3‐triazoles provides an opportunity to introduce additional functionality, however this simple functionalisation strategy using triazoles bearing electron‐withdrawing N‐substituents has not been investigated until now. Herein, we demonstrate that the lithiated triazole intermediates can readily decompose, even at −78 °C. In addition, lithiation‐deuteration studies reveal lithiation can take place competitively on both the triazole and the electron‐withdrawn aryl ring. Careful control of reaction conditions is therefore required to i) minimise decomposition pathways; and ii) facilitate regioselective functionalisation of the triazole.

  DOI：

  10.1002/ejoc.202201459
• 作为产物：
  描述：

  对甲苯磺酸正辛酯 在 sodium azide 、 copper(ll) sulfate pentahydrate 、 potassium carbonate 、 sodium ascorbate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.28h， 生成 1-octyl-4-phenyl-1H-[1,2,3]triazole
  参考文献：
  名称：

  A dicationic, podand-like, ionic liquid water system accelerated copper-catalyzed azide-alkyne click reaction

  摘要：

  In this work, an effective, task specific, dicationic, podand-like ionic liquid was synthesized and applied to improve the capability features of click reaction. Moreover, to broaden the scope and decreasing the serious limitations of preparation methods of organic azides, a simple green procedure for the preparation of alkyl azides, the fundamental starting materials in click reactions, from alcohols under solvent-free conditions and microwave irradiation has been reported, for the first time. (C) 2014 Mohammad Javaherian. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2014.09.005

文献信息

• Direct Synthesis of Organic Azides from Alcohols Using 2-Azido-1,3-dimethyl­imidazolinium Hexafluorophosphate
  作者：Mitsuru Kitamura、Tatsuya Koga、Masakazu Yano、Tatsuo Okauchi

  DOI：10.1055/s-0031-1290958

  日期：2012.6

  Direct synthesis of organic azides from alcohols was developed. Azide transfer of 2-azido-1,3-dimethylimidazolinium hexafluorophosphate (ADMP) to alcohols proceeds to give the corresponding azides under mild reaction conditions, which were easily isolated because the byproducts are highly soluble in water.

  开发了由醇直接合成有机叠氮化物。在温和的反应条件下，2-叠氮基-1,3-二甲基咪唑啉鎓六氟磷酸酯 (ADMP) 的叠氮化物转移到醇中，得到相应的叠氮化物，由于副产物高度溶于水，因此很容易分离。
• Impregnated copper ferrite on mesoporous graphitic carbon nitride: An efficient and reusable catalyst for promoting ligand‐free click synthesis of diverse 1,2,3‐triazoles and tetrazoles
  作者：Dariush Khalili、Meysam Rezaee

  DOI：10.1002/aoc.5219

  日期：2019.11

  Magnetic CuFe2O4/g‐C3N4 hybrids were synthesized through a facile method and their catalytic performances were evaluated in click chemistry for the first time. The structural and morphological characterization of prepared materials was carried out by different techniques such as X‐ray diffraction, high‐resolution transmission electron microscopy, field emission scanning electron microscopy, Fourier

  通过简便的方法合成了磁性CuFe 2 O 4 / g-C 3 N 4杂化物，并首次在点击化学中评估了它们的催化性能。所制备材料的结构和形态表征是通过不同的技术进行的，例如X射线衍射，高分辨率透射电子显微镜，场发射扫描电子显微镜，傅立叶红外光谱，振动样品磁力分析，热重分析和N 2吸附–解吸分析（Brunauer-Emmett-Teller表面积）。磁性CuFe 2 O 4 / g‐C 3 N 4的利用率使用烷基卤和环氧化物作为叠氮化物前体，可在水中进行一锅叠氮化物-炔烃环加成反应中获得优异性能，而无需任何其他试剂。本系统的范围很广，对于大环三唑以及四唑的合成特别实用。此外，该催化系统具有便利的条件，特别是在低催化剂负载量下易于获得各种重要产品，并且易于操作和分离的方法，可高度满足“绿色点击化学”的要求。
• Phosphoramidite accelerated copper(i)-catalyzed [3 + 2] cycloadditions of azides and alkynes
  作者：Lachlan S. Campbell-Verduyn、Leila Mirfeizi、Rudi A. Dierckx、Philip H. Elsinga、Ben L. Feringa

  DOI：10.1039/b822994e

  日期：——

  Monodentate phosphoramidite ligands are used to accelerate the copper(i)-catalyzed 1,3-dipolar cycloaddition of azides and alkynes (CuAAC) rapidly yielding a wide variety of functionalized 1,4-disubstituted-1,2,3-triazoles; Cu(i) and Cu(ii) salts both function as the copper source in aqueous solution to provide excellent yields.

  单齿亚磷酰胺配体可用于加速铜（i）催化的叠氮化物和炔烃（CuAAC）的1,3-偶极环加成反应，从而迅速生成各种官能化的1,4-二取代-1,2,3-三唑。Cu（i）和Cu（ii）盐均充当水溶液中的铜源，以提供优异的收率。
• Visible‐Light‐Mediated Click Chemistry for Highly Regioselective Azide–Alkyne Cycloaddition by a Photoredox Electron‐Transfer Strategy
  作者：Zheng‐Guang Wu、Xiang‐Ji Liao、Li Yuan、Yi Wang、You‐Xuan Zheng、Jing‐Lin Zuo、Yi Pan

  DOI：10.1002/chem.202000252

  日期：2020.5.4

  Click chemistry focuses on the development of highly selective reactions using simple precursors for the exquisite synthesis of molecules. Undisputedly, the CuI -catalyzed azide-alkyne cycloaddition (CuAAC) is one of the most valuable examples of click chemistry, but it suffers from some limitations as it requires additional reducing agents and ligands as well as cytotoxic copper. Here, we demonstrate

  Click化学专注于使用简单的前体进行分子的精细合成的高选择性反应的开发。毋庸置疑，CuI催化的叠氮化物-炔烃环加成（CuAAC）是点击化学最有价值的例子之一，但由于需要额外的还原剂和配体以及细胞毒性铜，因此受到一些限制。在这里，我们展示了一种新颖的叠氮化物-炔烃环加成反应的策略，该策略涉及光氧化还原电子转移自由基机理，而不是传统的金属催化配位过程。这种新开发的光催化的叠氮化物-炔烃环加成反应可以在室温下，在空气和可见光存在的条件下，在温和条件下进行，显示出良好的官能团耐受性，优异的原子经济性，高达99％的高收率，和绝对的区域选择性，提供了各种1,4-二取代的1,2,3-三唑衍生物，包括生物活性分子和药物。使用可回收的光催化剂，太阳能和水作为溶剂，使该光催化系统具有可持续性和环境友好性。此外，叠氮化物-炔烃环加成反应可以在具有优异区域选择性的无金属催化剂的存在下进行光催化，这代表了点击化学
• Dual roles of substituted thiourea as reductant and ligand in CuAAC reaction
  作者：Siyu Wang、Kai Jia、Jiajia Cheng、Yu Chen、Yaofeng Yuan

  DOI：10.1016/j.tetlet.2017.08.029

  日期：2017.9

  efficient catalytic system, CuSO4·5H2O/1-(4-methoxyphenyl)-3-phenylthiourea, for the copper(I)-catalyzed azide–alkyne cycloaddition reaction (CuAAC) was discovered. In the above catalytic system, substituted thiourea acts both as a reductant and a ligand. CuSO4·5H2O/1-(4-methoxyphenyl)-3-phenylthiourea is both an economical and efficient catalyst for the CuAAC reaction. In addition, the new catalytic system

  发现了一种高效的催化体系CuSO 4 ·5H 2 O / 1-（4-甲氧基苯基）-3-苯基硫脲，用于铜（I）催化的叠氮化物-炔烃环加成反应（CuAAC）。在上述催化体系中，取代的硫脲既充当还原剂又充当配体。CuSO 4 ·5H 2 O / 1-（4-甲氧基苯基）-3-苯基硫脲是CuAAC反应的经济有效的催化剂。此外，新的催化系统具有有利的功能，包括温和的绿色反应条件以及广泛的底物相容性。用CuSO 4 ·5H 2制备了各种具有良好产率的1,4-二取代的1,2,3-三唑O / 1-（4-甲氧基苯基）-3-苯基硫脲在水溶液中的催化体系。