1-辛基-5-苯基-1H-[1,2,3]三唑 | 1009089-58-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-辛基-5-苯基-1H-[1,2,3]三唑
• 英文名称: 1-octyl-5-phenyl-1H-[1,2,3]triazole
• 英文别名: 1-octyl-5-phenyl-1H-1,2,3-triazole
• CAS: 1009089-58-0
• 化学式: C₁₆H₂₃N₃
• 分子量: 257.379
• InChiKey: KNMSJZQSGHDYCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.31
• 重原子数：
  19.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  30.71
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  2-(benzo[d]thiazol-2-ylsulfonyl)-1-phenylethan-1-ol 在 吡啶 、 甲基磺酰氯 作用下， 以 水 为溶剂， 反应 10.0h， 生成 1-辛基-5-苯基-1H-[1,2,3]三唑
  参考文献：
  名称：

  A Metal-Free, Aqueous and General Route to 1,5-Disubstituted-1,2,3-triazoles: ‘Reversed Regioisomeric’ 1,3-Dipolar Cycloaddition of Azides and Vinyl Sulfones

  摘要：

  首次报道了一种无金属的基于乙烯基磺酰的1,5-二取代-1,2,3-三唑的合成方法。这些三唑可以通过在水相中加热回流甲基取代的乙烯基磺酰和有机叠氮化合物的混合物，以区域选择性的方式轻易形成。这条强大且实用的路线有潜力用于合成复杂的1,5-二取代-1,2,3-三唑。

  DOI：

  10.1055/s-0030-1260306

文献信息

• Cu²⁺-doped zeolitic imidazolate frameworks (ZIF-8): efficient and stable catalysts for cycloadditions and condensation reactions
  作者：Aleksandra Schejn、Abdelhay Aboulaich、Lavinia Balan、Véronique Falk、Jacques Lalevée、Ghouti Medjahdi、Lionel Aranda、Kevin Mozet、Raphaël Schneider

  DOI：10.1039/c4cy01505c

  日期：——

  Condensations and cycloadditions can be catalyzed by newly synthesized Cu-doped zeolitic imidazolate frameworks (ZIFs). The catalysts were well characterized and reusable.

  凝聚和环加成可以通过新合成的Cu掺杂沸石咪唑酸盐骨架（ZIFs）进行催化。这些催化剂经过了良好的表征，可重复使用。
• A recyclable ruthenium(ii) complex supported on magnetic nanoparticles: a regioselective catalyst for alkyne–azide cycloaddition
  作者：Dong Wang、Lionel Salmon、Jaime Ruiz、Didier Astruc

  DOI：10.1039/c3cc43048k

  日期：——

  A magnetically separable ruthenium catalyst was synthesized through immobilizing a pentamethylcyclopentadienyl ruthenium complex on iron oxide nanoparticles. The catalyst is highly active and selective for the synthesis of 1,5-disubstituted 1,2,3-trizoles via cycloaddition of alkynes and organic azides and can be recycled at least 5 times.

  通过将五甲基环戊二烯基钌络合物固定在氧化铁纳米颗粒上来合成可磁分离的钌催化剂。该催化剂对炔烃和有机叠氮化物的环加成反应具有很高的活性，对合成1,5-二取代的1,2,3-三唑具有选择性，可循环使用至少5次。
• A general route to 1,5-disubstituted 1,2,3-triazoles with alkyl/alkyl, alkyl/aryl, aryl/aryl combinations: a metal-free, regioselective, one-pot three component approach
  作者：Santu Dey、Tanmaya Pathak

  DOI：10.1039/c3ra47062h

  日期：——

  An experimentally simple one-pot reaction, affording 1,5-disubstituted 1H-1,2,3-triazoles in good to excellent yields by combining vinyl sulfones, sodium azide and alkyl bromides, -tosylates, -mesylates or aryl amines, -iodides is reported. The organic azides, generated in situ react with vinyl sulfones in a regioselective fashion in the absence of metal ions. Unlike many of the recently reported strategies, this method is capable of generating alkyl/alkyl, alkyl/aryl and aryl/aryl containing 1,5-disubstituted 1,2,3-triazoles under simple reaction conditions.

  本报告介绍了一种实验简单的一锅反应，通过将乙烯基砜、叠氮化钠和烷基溴化物、-对甲苯磺酸盐、-甲磺酸盐或芳基胺、-碘化物结合在一起，可以得到 1,5-二取代的 1H-1,2,3-三唑，收率从良好到极佳。在没有金属离子的情况下，原位生成的有机叠氮化物以区域选择性的方式与乙烯基砜发生反应。与最近报道的许多策略不同，这种方法能够在简单的反应条件下生成烷基/烷基、烷基/芳基和芳基/芳基的 1,5 二甲基 1,2,3 三唑。
• Copper(I)-Catalyzed Direct Arylation of 1,4-Disubstituted 1,2,3-Triazoles with Aryl Iodides
  作者：Shin-ichi Fukuzawa、Eiji Shimizu、Kenichi Ogata

  DOI：10.3987/com-08-11546

  日期：——

  Treatment of 1,4-disubstituted 1,2,3-triazoles with aryl iodides in the presence of a catalytic amount of copper chloride and lithium tert-butoxide (stoichiometric) in DMF at 140 degrees C leads to arylation at the 5-position. Various combinations of substituted aryl iodides and 1,4-disubstituted 1,2,3-triazoles bearing functional groups were found to be compatible.
• A tunable route to oxidative and eliminative [3+2] cycloadditions of organic azides with nitroolefins: CuO nanoparticles catalyzed synthesis of 1,2,3-triazoles under solvent-free condition
  作者：D. Gangaprasad、J. Paul Raj、T. Kiranmye、R. Sasikala、K. Karthikeyan、S. Kutti Rani、J. Elangovan

  DOI：10.1016/j.tetlet.2016.06.004

  日期：2016.7

  A regioselective and tunable synthesis of 1,5-disubstituted 1,2,3-triazloles from oxidative and eliminative [3+2] cycloadditions of nitroolefins and organic azides under solvent-free condition in the presence and absence of commercially available CuO nanoparticle catalyst is described. In the presence of the catalyst under solvent-free condition, nitro group is retained in the product while it gets eliminated in the absence of the catalyst. (C) 2016 Elsevier Ltd. All rights reserved.