1-(1-(n-octyl)-1H-1,2,3-triazol-4-yl)-2-phenylethanone | 1345823-30-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(1-(n-octyl)-1H-1,2,3-triazol-4-yl)-2-phenylethanone
• 英文别名: 1-(1-Octyltriazol-4-yl)-2-phenyl-ethanone；1-(1-octyltriazol-4-yl)-2-phenylethanone
• CAS: 1345823-30-4
• 化学式: C₁₈H₂₅N₃O
• 分子量: 299.416
• InChiKey: NEIKOWPQBLXIFZ-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：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  47.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(1-(n-octyl)-1H-1,2,3-triazol-4-yl)-2-phenylethanone 在 copper(l) iodide 、 新铜试剂 作用下， 以 乙腈 为溶剂， 以48%的产率得到1-(1-octyl-1H-1,2,3-triazol-4-yl)-2-phenylethane-1,2-dione
  参考文献：
  名称：

  以三唑为分子内辅助基团的好氧铜催化氧化合成α,β-二酮三唑

  摘要：

  用 CuCl2 或 CuI/2,9-二甲基-1,10-菲咯啉在 80°C 的空气中以良好的产率将 α-酮三唑催化氧化为 α,β-二酮三唑。研究表明，三唑基团参与与铜的络合并有利于氧化。

  DOI：

  10.1002/ejoc.201101346
• 作为产物：
  描述：

  1-溴辛烷 在 sodium azide 、 sodium ascorbate 、 copper dichloride 作用下， 以 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 1-(1-(n-octyl)-1H-1,2,3-triazol-4-yl)-2-phenylethanone
  参考文献：
  名称：

  Synthesis and biological activities of triazole derivatives as inhibitors of InhA and antituberculosis agents

  摘要：

  InhA, the enoyl reductase from the mycobacterial type II fatty acid biosynthesis pathway, is a target for the development of novel drugs against tuberculosis. We exploited copper-catalyzed [3+2] cycloaddition between alkynes and different azides to afford 1,4-disubstituted triazole or alpha-ketotriazole derivatives. Several compounds bearing a lipophilic chain mimicking the substrate were able to inhibit InhA. Among them, 1-dodecyl-4-phenethyl-1H-1,2,3-triazole displayed a minimum inhibitory concentration inferior to 2 mu g/mL against Mycobacterium tuberculosis H37Rv. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.09.013

文献信息

• Synthesis and evaluation of α-ketotriazoles and α,β-diketotriazoles as inhibitors of Mycobacterium tuberculosis
  作者：Christophe Menendez、Frédéric Rodriguez、Ana Luisa de Jesus Lopes Ribeiro、Francesca Zara、Céline Frongia、Valérie Lobjois、Nathalie Saffon、Maria Rosalia Pasca、Christian Lherbet、Michel Baltas

  DOI：10.1016/j.ejmech.2013.06.042

  日期：2013.11

  Two series of alpha-ketotriazole and alpha,beta-diketotriazole derivatives were synthesized and evaluated for antitubercular and cytotoxic activities. Among them, two alpha,beta-diketotriazole compounds, 6b and 9b, exhibited good activities (minimum inhibitory concentration = 7.6 mu M and 6.9 mu M, respectively) on Mycobacterium tuberculosis and multi-drug resistant M. tuberculosis strains and presented no cytotoxicity (IC50 > 50 mu M) on colorectal cancer HCT116 and normal fibroblast GM637H cell lines. These two compounds represent promising leads for further optimization. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Synthesis and biological activities of triazole derivatives as inhibitors of InhA and antituberculosis agents
  作者：Christophe Menendez、Sylvain Gau、Christian Lherbet、Frédéric Rodriguez、Cyril Inard、Maria Rosalia Pasca、Michel Baltas

  DOI：10.1016/j.ejmech.2011.09.013

  日期：2011.11

  InhA, the enoyl reductase from the mycobacterial type II fatty acid biosynthesis pathway, is a target for the development of novel drugs against tuberculosis. We exploited copper-catalyzed [3+2] cycloaddition between alkynes and different azides to afford 1,4-disubstituted triazole or alpha-ketotriazole derivatives. Several compounds bearing a lipophilic chain mimicking the substrate were able to inhibit InhA. Among them, 1-dodecyl-4-phenethyl-1H-1,2,3-triazole displayed a minimum inhibitory concentration inferior to 2 mu g/mL against Mycobacterium tuberculosis H37Rv. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Synthesis of α,β-Diketotriazoles by Aerobic Copper-Catalyzed Oxygenation with Triazole as an Intramolecular Assisting Group
  作者：Christophe Menendez、Sylvain Gau、Sonia Ladeira、Christian Lherbet、Michel Baltas

  DOI：10.1002/ejoc.201101346

  日期：2012.1

  The catalytic oxidation of α-ketotriazoles to α,β-diketotriazoles was performed with CuCl2 or CuI/2,9-dimethyl-1,10-phenanthroline in air at 80 °C in good yields. Studies showed that the triazole group participates in complexation to the copper and favors oxidation.

  用 CuCl2 或 CuI/2,9-二甲基-1,10-菲咯啉在 80°C 的空气中以良好的产率将 α-酮三唑催化氧化为 α,β-二酮三唑。研究表明，三唑基团参与与铜的络合并有利于氧化。