1-benzyl-N-prop-2-ynyltriazole-4-carboxamide | 1245932-54-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-benzyl-N-prop-2-ynyltriazole-4-carboxamide
• CAS: 1245932-54-0
• 化学式: C₁₃H₁₂N₄O
• 分子量: 240.264
• InChiKey: BVQXAGMZUYWYCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  59.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-benzyl-N-prop-2-ynyltriazole-4-carboxamide 、 苄基叠氮 在 copper(l) iodide 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到1-benzyl-N-[(1-benzyltriazol-4-yl)methyl]triazole-4-carboxamide
  参考文献：
  名称：

  Chemoselective preparation of disymmetric bistriazoles from bisalkynes

  摘要：

  Best of both worlds, molecules bearing two alkyne groups, activated and unactivated, can selectively react on the activated one in a copper-free version of Huisgen's reaction to form a first triazole ring, with a good selectivity toward the 1,4-isomer, which is solely isolated by a simple trituration procedure. The other alkyne function is then submitted to the selective reaction using a polymer-supported copper(I) catalyst to form a second triazole ring. This gave access to disymmetric bistriazoles without the need of protection using simple, easy, and fast procedures. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.11.141
• 作为产物：
  描述：

  溴甲苯 在 sodium azide 作用下， 以 neat (no solvent) 为溶剂， 反应 18.0h， 生成 1-benzyl-N-prop-2-ynyltriazole-4-carboxamide
  参考文献：
  名称：

  Synthesis and in vitro evaluation of potential anticancer activity of mono- and bis-1,2,3-triazole derivatives of bis-alkynes

  摘要：

  In order to find new molecules with cytotoxic activity against cancer cells, we prepared bis-akyne amides derived from propiolic acid. The bis-alkynes were then transformed in their mono-1,2,3-triazole analogs onto the amide side, due to its greater reactivity, using a catalyst-free Huisgen's reaction. The mono-triazoles were then subjected to the copper (I)-catalyzed version of the previous reaction (CuAAC), using a supported catalyst, to produce bis-triazoles. All products were obtained pure after simple trituration or filtration procedures. All synthetic compounds were tested in vitro for their cytotoxic activity using B16 melanoma cells. Four compounds (7, 23, 25 and 33) showed activities in the micromolar range (<21 mu M) whereas three compounds (3, 22 and 38) presented activity at low micromolar concentrations (<10 mu M), and two analogs (2 and 13) were active at nanomolar levels (<1 mu M). (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.12.025

文献信息

• On the reactivity of activated alkynes in copper and solvent-free Huisgen’s reaction
  作者：Hichem Elamari、Ibtissem Jlalia、Charlotte Louet、Jean Herscovici、Faouzi Meganem、Christian Girard

  DOI：10.1016/j.tetasy.2010.06.013

  日期：2010.5

  Terminal alkynes substituted by a carbonyl-type electron-withdrawing group have been found to undergo Huisgen's cycloaddition with azides at room temperature in a solvent-free manner; without a need of either heating or catalysis. Metallic salts, other than the copper ones also efficiently catalyzed the reactions. The yields were good and the products isolated mainly as their 1,4-disubstituted isomer. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis and in vitro evaluation of potential anticancer activity of mono- and bis-1,2,3-triazole derivatives of bis-alkynes
  作者：Hichem Elamari、Riadh Slimi、Guy G. Chabot、Lionel Quentin、Daniel Scherman、Christian Girard

  DOI：10.1016/j.ejmech.2012.12.025

  日期：2013.2

  In order to find new molecules with cytotoxic activity against cancer cells, we prepared bis-akyne amides derived from propiolic acid. The bis-alkynes were then transformed in their mono-1,2,3-triazole analogs onto the amide side, due to its greater reactivity, using a catalyst-free Huisgen's reaction. The mono-triazoles were then subjected to the copper (I)-catalyzed version of the previous reaction (CuAAC), using a supported catalyst, to produce bis-triazoles. All products were obtained pure after simple trituration or filtration procedures. All synthetic compounds were tested in vitro for their cytotoxic activity using B16 melanoma cells. Four compounds (7, 23, 25 and 33) showed activities in the micromolar range (<21 mu M) whereas three compounds (3, 22 and 38) presented activity at low micromolar concentrations (<10 mu M), and two analogs (2 and 13) were active at nanomolar levels (<1 mu M). (C) 2012 Elsevier Masson SAS. All rights reserved.
• Chemoselective preparation of disymmetric bistriazoles from bisalkynes
  作者：Hichem Elamari、Faouzi Meganem、Jean Herscovici、Christian Girard

  DOI：10.1016/j.tetlet.2010.11.141

  日期：2011.2

  Best of both worlds, molecules bearing two alkyne groups, activated and unactivated, can selectively react on the activated one in a copper-free version of Huisgen's reaction to form a first triazole ring, with a good selectivity toward the 1,4-isomer, which is solely isolated by a simple trituration procedure. The other alkyne function is then submitted to the selective reaction using a polymer-supported copper(I) catalyst to form a second triazole ring. This gave access to disymmetric bistriazoles without the need of protection using simple, easy, and fast procedures. (C) 2010 Elsevier Ltd. All rights reserved.