1-benzyl-4-butyl-5-phenyl-1H-1,2,3-triazole | 1379671-46-1

• 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-benzyl-4-butyl-5-phenyl-1H-1,2,3-triazole
• 英文别名: 1-Benzyl-4-butyl-5-phenyltriazole；1-benzyl-4-butyl-5-phenyltriazole
• CAS: 1379671-46-1
• 化学式: C₁₉H₂₁N₃
• 分子量: 291.396
• InChiKey: DUPMSAKOEUPCII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  溴甲苯 在 sodium azide 、 2,6-二叔丁基-4-甲基苯酚 、 morpholinium para-toluenesulfonate 作用下， 以 水 、 丙酮 、 甲苯 为溶剂， 反应 79.0h， 生成 1-benzyl-4-butyl-5-phenyl-1H-1,2,3-triazole
  参考文献：
  名称：

  无金属三组分反应用于区域选择性合成1,4,5-三取代的1,2,3-三唑

  摘要：

  本文描述了一种无金属的三组分反应，该反应可从容易获得的结构单元（如醛，硝基烷和有机叠氮化物）中合成1,4,5-三取代的1,2,3-三唑。该过程是通过甲酰基与硝基化合物的有机催化的Knoevenagel缩合实现的，然后将叠氮化物进行1,3-偶极环加成反应生成活化的烯烃。该反应具有优异的底物范围，并且以高收率和区域选择性获得产物。该方法可用于合成稠合的三唑杂环和具有几个三唑部分的材料。

  DOI：

  10.1002/anie.201403453

文献信息

• Pd-NHC-Catalyzed Direct Arylation of 1,4-Disubstituted 1,2,3-Triazoles with Aryl Halides
  作者：Tao He、Min Wang、Pinhua Li、Lei Wang

  DOI：10.1002/cjoc.201100275

  日期：2012.4

  highly efficient method for the synthesis of unsymmetrical multi‐substituted 1,2,3‐triazoles via a direct Pd‐NHC system catalyzed C(5)‐arylation of 1,4‐disubstituted triazoles, which are readily accessible via "click" chemistry has been developed. It is important to note that CH bond functionalizations of 1,2,3‐triazoles with a variety of differently substituted aryl iodides and bromides as electrophiles

  一种通过直接的Pd-NHC系统催化不对称多取代1,2,3-三唑的高效方法，催化1,4-二取代三唑的C（5）芳基化，可通过“点击”化学轻松获得已经被开发出来。重要的是要注意，通过这种催化体系，可以在空气中100°C的较温和的反应温度下，通过该催化体系方便地实现1,2,3-三唑与各种不同取代的芳基碘化物和溴化物的CH键官能化。 。
• C–H arylations of 1,2,3-triazoles by reusable heterogeneous palladium catalysts in biomass-derived γ-valerolactone
  作者：Xu Tian、Fanzhi Yang、Dace Rasina、Michaela Bauer、Svenja Warratz、Francesco Ferlin、Luigi Vaccaro、Lutz Ackermann

  DOI：10.1039/c6cc03468c

  日期：——

  C-H arylations were accomplished with a user-friendly heterogeneous palladium catalyst in the biomass-derived [gamma]-valerolactone (GVL) as an environmentally-benign reaction medium. The user-friendly protocol was characterized by ample substrate scope and...

  在用户友好的非均相钯催化剂中，在环境友好的反应介质中，在生物质衍生的γ-戊内酯（GVL）中实现CH芳基化。该用户友好协议的特点是具有足够的承印物范围和...
• Synthesis of 1,4,5-Trisubstituted 1,2,3-Triazoles Amicable for Automation
  作者：Mitta Kavitha、Bodugam Mahipal、Prathama Mainkar、Srivari Chandrasekhar

  DOI：10.2174/1386207311316080009

  日期：2013.8.1

  A three-component 3+2 cycloaddition reaction followed by Suzuki coupling reaction was carried out to synthesize a library of compounds using automation (parallel synthesizer). Scaffolds that are unexplored in literature were used for the synthesis of library. The iodo-triazoles formed by 3+2 cycloaddition reaction were coupled with boronic acids to get tri-substituted triazoles.

  进行三组分3 + 2环加成反应，然后进行Suzuki偶联反应，以使用自动化（并行合成仪）合成化合物库。文献中尚未探索的支架用于文库的合成。通过3 + 2环加成反应形成的碘代三唑与硼酸偶合得到三取代的三唑。
• ‘Green’ synthesis of 1,4-disubstituted 5-iodo-1,2,3-triazoles under neat conditions, and an efficient approach of construction of 1,4,5-trisubstituted 1,2,3-triazoles in one pot
  作者：Dong Wang、Si Chen、Baohua Chen

  DOI：10.1016/j.tetlet.2014.10.128

  日期：2014.12

  An environmentally friendly and efficient method for synthesis of 1,4-disubstituted 5-iodo-1,2,3-triazoles through [Cu(phen)(PPh3)2]NO3-catalyzed cycloaddition of organic azides and iodoalkynes under solvent-free conditions was developed. Based on this, a one-pot method for the synthesis of fully substituted 1,2,3-triazoles via cycloaddition/Suzuki reactions was also demonstrated in this report.

  在溶剂-溶剂中通过[Cu（phen）（PPh 3）2 ] NO 3催化有机叠氮化物和碘代炔烃环加成合成1,4-二取代的5-碘-1,2,3-三唑的环保，高效方法自由条件得以发展。在此基础上，本报告还证明了一锅法通过环加成/铃木反应合成完全取代的1,2,3-三唑。
• Cu/Pd-Catalyzed, Three-Component Click Reaction of Azide, Alkyne, and Aryl Halide: One-Pot Strategy toward Trisubstituted Triazoles
  作者：Fang Wei、Haoyu Li、Chuanling Song、Yudao Ma、Ling Zhou、Chen-Ho Tung、Zhenghu Xu

  DOI：10.1021/acs.orglett.5b01342

  日期：2015.6.5

  A Cu/Pd-catalyzed, three-component click reaction of azide, alkyne, and aryl halide has been developed. By using this Cu/Pd transmetalation relay catalysis, a variety of 1,4,5-trisubstituted 1,2,3-triazoles were quickly assembled in one step in high yields with complete regioselectivity, just like assembling Lego bricks. Notably, different from the well-established CuAAC click reactions only working on terminal alkynes, this reaction offers an alternative solution for the problem of the click reaction of internal alkynes.