1,3,5-tris(3-azido-2-hydroxypropyl)-1,3,5-triazinane-2,4,6-trione | 1000416-74-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: 1,3,5-tris(3-azido-2-hydroxypropyl)-1,3,5-triazinane-2,4,6-trione
• 英文别名: 1,3,5-Tris(3-azido-2-hydroxypropyl)-1,3,5-triazinane-2,4,6-trione
• CAS: 1000416-74-9
• 化学式: C₁₂H₁₈N₁₂O₆
• 分子量: 426.352
• InChiKey: PLHNWSIMIARVMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  165
• 氢给体数：
  3
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (4,4'-((prop-2-yn-1-ylazanediyl)bis(methylene))bis(2-methoxyphenol)) 、 1,3,5-tris(3-azido-2-hydroxypropyl)-1,3,5-triazinane-2,4,6-trione 在 铜 作用下， 以 四氢呋喃 为溶剂， 20.0~85.0 ℃ 、1.72 MPa 条件下， 反应 8.0h， 以82%的产率得到1,3,5-Tris[3-[4-[[bis[(4-hydroxy-3-methoxyphenyl)methyl]amino]methyl]triazol-1-yl]-2-hydroxypropyl]-1,3,5-triazinane-2,4,6-trione
  参考文献：
  名称：

  Copper-Granule-Catalyzed Microwave-Assisted Click Synthesis of Polyphenol Dendrimers

  摘要：

  Syringaldehyde- and vanillin-based antioxidant dendrimers were synthesized via microwave-assisted alkyne-azide 1,3-dipolar cydoaddition using copper granules as a catalyst. The use of Cu(I) as a catalyst resulted in copper contaminated dendrimers. To produce copper-free antioxidant dendrimers for biological applications, Cu(I) was substituted with copper granules. Copper granules were ineffective at both room temperature and under reflux conditions (<5% yield). However, they were an excellent catalyst when dendrimer synthesis was performed under microwave irradiation, giving yields up to 94% within 8 h. ICP-mass analysis of the antioxidant dendrimers obtained with this method showed virtually no copper contamination (9 ppm), which was the same as the background level. The synthesized antioxidants, free from copper contamination, demonstrated potent radical scavenging with IC50 values of less than 3 mu M in the 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay. In comparison, dendrimers synthesized from Cu(I)-catalyzed click chemistry showed a high level of copper contamination (4800 ppm) and no detectable antioxidant activity.

  DOI：

  10.1021/jo401603d
• 作为产物：
  描述：

  1,3,5-三缩水甘油-S-三嗪三酮 在 sodium azide 、 氯化铵 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 以55%的产率得到1,3,5-tris(3-azido-2-hydroxypropyl)-1,3,5-triazinane-2,4,6-trione
  参考文献：
  名称：

  Copper-Granule-Catalyzed Microwave-Assisted Click Synthesis of Polyphenol Dendrimers

  摘要：

  Syringaldehyde- and vanillin-based antioxidant dendrimers were synthesized via microwave-assisted alkyne-azide 1,3-dipolar cydoaddition using copper granules as a catalyst. The use of Cu(I) as a catalyst resulted in copper contaminated dendrimers. To produce copper-free antioxidant dendrimers for biological applications, Cu(I) was substituted with copper granules. Copper granules were ineffective at both room temperature and under reflux conditions (<5% yield). However, they were an excellent catalyst when dendrimer synthesis was performed under microwave irradiation, giving yields up to 94% within 8 h. ICP-mass analysis of the antioxidant dendrimers obtained with this method showed virtually no copper contamination (9 ppm), which was the same as the background level. The synthesized antioxidants, free from copper contamination, demonstrated potent radical scavenging with IC50 values of less than 3 mu M in the 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay. In comparison, dendrimers synthesized from Cu(I)-catalyzed click chemistry showed a high level of copper contamination (4800 ppm) and no detectable antioxidant activity.

  DOI：

  10.1021/jo401603d

文献信息

• Copper-Granule-Catalyzed Microwave-Assisted Click Synthesis of Polyphenol Dendrimers
  作者：Choon Young Lee、Rich Held、Ajit Sharma、Rom Baral、Cyprien Nanah、Dan Dumas、Shannon Jenkins、Samik Upadhaya、Wenjun Du

  DOI：10.1021/jo401603d

  日期：2013.11.15

  Syringaldehyde- and vanillin-based antioxidant dendrimers were synthesized via microwave-assisted alkyne-azide 1,3-dipolar cydoaddition using copper granules as a catalyst. The use of Cu(I) as a catalyst resulted in copper contaminated dendrimers. To produce copper-free antioxidant dendrimers for biological applications, Cu(I) was substituted with copper granules. Copper granules were ineffective at both room temperature and under reflux conditions (<5% yield). However, they were an excellent catalyst when dendrimer synthesis was performed under microwave irradiation, giving yields up to 94% within 8 h. ICP-mass analysis of the antioxidant dendrimers obtained with this method showed virtually no copper contamination (9 ppm), which was the same as the background level. The synthesized antioxidants, free from copper contamination, demonstrated potent radical scavenging with IC50 values of less than 3 mu M in the 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay. In comparison, dendrimers synthesized from Cu(I)-catalyzed click chemistry showed a high level of copper contamination (4800 ppm) and no detectable antioxidant activity.