4-hexyl-1-phenethyl-1H-1,2,3-triazole | 1049744-13-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-hexyl-1-phenethyl-1H-1,2,3-triazole
• 英文别名: 4-Hexyl-1-phenethyl-triazole；4-hexyl-1-(2-phenylethyl)triazole
• CAS: 1049744-13-9
• 化学式: C₁₆H₂₃N₃
• 分子量: 257.379
• InChiKey: VABKKSKNMCMUIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 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：

  4-hexyl-1-phenethyl-1H-1,2,3-triazole 在 copper dichloride 、 三甲基乙酸 作用下， 以 neat (no solvent) 为溶剂， 反应 46.0h， 以62%的产率得到5-chloro-4-hexyl-1-phenethyl-1H-1,2,3-triazole
  参考文献：
  名称：

  无溶剂新戊酸/氯化铜共同促进 1,2,3-三唑的氯化

  摘要：

  通过在新戊酸中使用氯化铜 (II)，直接从 5H 取代的 1,2,3-三唑在 1,2,3-三唑的 5-位上开发了一种新的氯化反应。因此，一系列三唑以低到高的收率被氯化。

  DOI：

  10.1055/s-0032-1317446
• 作为产物：
  描述：

  乙基溴苯 在 sodium azide 、 copper(II) sulfate 、 sodium ascorbate 、 sodium iodide 作用下， 以 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 24.0h， 生成 4-hexyl-1-phenethyl-1H-1,2,3-triazole
  参考文献：
  名称：

  Chemical synthesis and biological evaluation of triazole derivatives as inhibitors of InhA and antituberculosis agents

  摘要：

  A series of triazoles have been prepared and evaluated as inhibitors of InhA as well as inhibitors of Mycobacterium tuberculosis H37Rv. Several of these new compounds possess a good activity against InhA, particularly compounds 17 and 18 for which molecular docking has been performed. Concerning their activities against M. tuberculosis H37Rv strain, two of them, 3 and 12, were found to be good inhibitors with MIC values of 0.50 and 0.25 mu g/ml, respectively. Particularly, compound 12 presenting the best MIC value of all compounds tested (0.6 mu M) is totally inactive against InhA. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.03.029

文献信息

• An efficient Cu-catalyzed azide–alkyne cycloaddition (CuAAC) reaction in aqueous medium with a zwitterionic ligand, betaine
  作者：Jung-Ah Shin、Su-Jin Oh、Hee-Yoon Lee、Yeong-Gweon Lim

  DOI：10.1039/c7cy00518k

  日期：——

  Cu-catalyzed azide–alkyne cycloaddition reaction in aqueous medium was dramatically accelerated by a simple zwitterionic additive, betaine, at ambient temperature. In the presence of betaine, 1,4-disubstituted-1,2,3-triazoles were obtained from azides and terminal alkynes in excellent yields under 2.5–200 ppm levels of Cu(I) in water. This method resulted in the remarkable reduction of the Cu(I) concentration

  在环境温度下，简单的两性离子添加剂甜菜碱可显着促进水介质中铜催化的叠氮化物-炔烃环加成反应。在甜菜碱存在的情况下，在2.5–200 ppm的水中铜（I）水平下，叠氮化物和末端炔烃可得到1,4-二取代-1,2,3-三唑。该方法导致Cu （I）浓度显着降低至ppm级。该方案的优点包括使用常规的Cu催化体系和可商购获得的甜菜碱，该甜菜碱对生物应用通常是无毒的。因此，这种有效的催化体系应在生命科学研究和材料科学中具有广泛的应用。
• A Rapid Click Chemistry Using Beta-Cyclodextrin Immobilized on Glass Micro-Particles
  作者：Muhammad Nazir Tahir、Riaz-ul Qamar、Petra Mischnick、Jaebum Kim、Seunho Jung

  DOI：10.2174/1570178611310040008

  日期：2013.4.30

  The surface of glass micro-particle (GMP) was functionalized with β-cyclodextrin (→ GMP-β-CD) and was characterized by X-ray photoelectron spectroscopy (XPS). GMP-β-CD was used as a phase transfer catalyst for click reactions of aromatic azides with terminal acetylenes. For click reaction of benzyl azide and phenyl acetylene, reaction time was decreased from 5.8 h to 10 min when 0.8g GMP-β-CD /mmol of benzyl azide was added. The modified surface of GMP-β-CD showed no change or degradation after repeated use as confirmed from XPS analysis after 10 cycles.

  玻璃微粒（GMP）的表面经过β-环状糊精功能化（→ GMP-β-CD），并通过X射线光电子能谱（XPS）进行表征。GMP-β-CD被用作芳香族叠氮化物与末端炔烃之间点击反应的相转移催化剂。对于苄基叠氮化物和苯烯的点击反应，当加入0.8克GMP-β-CD/毫摩尔苄基叠氮化物时，反应时间从5.8小时减少到10分钟。经过10个循环后的XPS分析确认，GMP-β-CD的改性表面在重复使用后没有变化或降解。
• Copper-Catalyzed Azide–Alkyne Cycloaddition Reaction in Water Using Cyclodextrin as a Phase Transfer Catalyst
  作者：Jung-Ah Shin、Yeong-Gweon Lim、Kyung-Hee Lee

  DOI：10.1021/jo3000095

  日期：2012.4.20

  1,4-Disubstituted-1,2,3-triazoles were obtained in excellent yields from azides and terminal alkynes in H2O in the presence of catalytic amount of beta-cyclodextrin as a phase transfer catalyst. Also, a one-pot CuAAC reaction was carried out successfully, affording 1,4-disubstituted-1,2,3-triazoles in good to high yields starting from an alkyl bromide, sodium azide, and terminal alkyne.
• Chemical synthesis and biological evaluation of triazole derivatives as inhibitors of InhA and antituberculosis agents
  作者：Christophe Menendez、Aurélien Chollet、Frédéric Rodriguez、Cyril Inard、Maria Rosalia Pasca、Christian Lherbet、Michel Baltas

  DOI：10.1016/j.ejmech.2012.03.029

  日期：2012.6

  A series of triazoles have been prepared and evaluated as inhibitors of InhA as well as inhibitors of Mycobacterium tuberculosis H37Rv. Several of these new compounds possess a good activity against InhA, particularly compounds 17 and 18 for which molecular docking has been performed. Concerning their activities against M. tuberculosis H37Rv strain, two of them, 3 and 12, were found to be good inhibitors with MIC values of 0.50 and 0.25 mu g/ml, respectively. Particularly, compound 12 presenting the best MIC value of all compounds tested (0.6 mu M) is totally inactive against InhA. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Solvent-Free Pivalic Acid/Copper Chloride Jointly Promoted Chlorination of 1,2,3-Triazoles
  作者：Christian Lherbet、Michel Baltas、Christophe Menendez、Nathalie Saffon

  DOI：10.1055/s-0032-1317446

  日期：——

  A novel chlorination reaction on the 5-position of 1,2,3-triazoles, directly from 5H-substituted 1,2,3-triazoles was developed by using copper(II) chloride in pivalic acid. A series of triazoles were thus chlorinated in low to good yields.

  通过在新戊酸中使用氯化铜 (II)，直接从 5H 取代的 1,2,3-三唑在 1,2,3-三唑的 5-位上开发了一种新的氯化反应。因此，一系列三唑以低到高的收率被氯化。