1-(4-chlorophenyl)-2-(4-p-tolyl-1H-1,2,3-triazol-1-yl)ethanone | 1150635-22-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-chlorophenyl)-2-(4-p-tolyl-1H-1,2,3-triazol-1-yl)ethanone
• 英文别名: 1-(4-chlorophenyl)-2-[4-(4-methylphenyl)triazol-1-yl]ethanone
• CAS: 1150635-22-5
• 化学式: C₁₇H₁₄ClN₃O
• 分子量: 311.771
• InChiKey: GUNLZKFSGRRUOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  47.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-甲苯基乙炔 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium azide 、 copper(II) sulfate 、 sodium ascorbate 作用下， 以 水 为溶剂， 反应 1.0h， 生成 1-(4-chlorophenyl)-2-(4-p-tolyl-1H-1,2,3-triazol-1-yl)ethanone
  参考文献：
  名称：

  Click chemistry inspired one-pot synthesis of 1,4-disubstituted 1,2,3-triazoles and their Src kinase inhibitory activity

  摘要：

  Two classes of 1,4-disubstituted 1,2,3-triazoles were synthesized using one-pot reaction of alpha-tosyloxy ketones/alpha-halo ketones, sodium azide, and terminal alkynes in the presence of aq PEG (1: 1, v/v) using the click chemistry approach and evaluated for Src kinase inhibitory activity. Structure-activity relationship analysis demonstrated that insertion of C6H5- and 4-CH3C6H4- at position 4 for both classes and less bulkier aromatic group at position 1 in class 1 contribute critically to the modest Src inhibition activity (IC50 = 32-43 mu M) of 1,4-disubstituted 1,2,3-triazoles. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.10.121

文献信息

• Greener and Expeditious Synthesis of 1,4-Disubstituted 1,2,3-Triazoles from Terminal Acetylenes and in situ Generated α-Azido Ketones
  作者：Dalip Kumar、Gautam Patel、V. Reddy

  DOI：10.1055/s-0028-1087556

  日期：2009.2

  A convenient and mild protocol for the one-pot regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles in aqueous PEG 400 has been reported. The methodology involves the one-pot reaction ofa-bromo ketones, sodium azide, and terminal acetylenes catalyzed by Cu(I) in aqueous PEG 400 at room temperature. Prominent features of our approach are mild reaction conditions, use of readily available α-bromo

  已经报道了一种在水性 PEG 400 中一锅区域选择性合成 1,4-二取代 1,2,3-三唑的方便和温和的协议。该方法涉及在室温下在水性 PEG 400 中由 Cu(I) 催化的 α-溴酮、叠氮化钠和末端乙炔的一锅反应。我们方法的突出特点是反应条件温和、使用容易获得的 α-溴化合物、水性 PEG 400 作为良性反应介质、避免分离不稳定的 α-叠氮酮、简单的后处理和良好的收率。
• Click chemistry inspired one-pot synthesis of 1,4-disubstituted 1,2,3-triazoles and their Src kinase inhibitory activity
  作者：Dalip Kumar、V. Buchi Reddy、Anil Kumar、Deendayal Mandal、Rakesh Tiwari、Keykavous Parang

  DOI：10.1016/j.bmcl.2010.10.121

  日期：2011.1

  Two classes of 1,4-disubstituted 1,2,3-triazoles were synthesized using one-pot reaction of alpha-tosyloxy ketones/alpha-halo ketones, sodium azide, and terminal alkynes in the presence of aq PEG (1: 1, v/v) using the click chemistry approach and evaluated for Src kinase inhibitory activity. Structure-activity relationship analysis demonstrated that insertion of C6H5- and 4-CH3C6H4- at position 4 for both classes and less bulkier aromatic group at position 1 in class 1 contribute critically to the modest Src inhibition activity (IC50 = 32-43 mu M) of 1,4-disubstituted 1,2,3-triazoles. (c) 2010 Elsevier Ltd. All rights reserved.