1-benzyl-1'-(4-tert-butylbenzyl)-5'-iodo-1H,1'H-4,4'-bis(1,2,3-triazole) | 1218787-72-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-benzyl-1'-(4-tert-butylbenzyl)-5'-iodo-1H,1'H-4,4'-bis(1,2,3-triazole)
• CAS: 1218787-72-4
• 化学式: C₂₂H₂₃IN₆
• 分子量: 498.369
• InChiKey: VVWXLZZWVMCALJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.54
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  61.42
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-benzyl-1'-(4-tert-butylbenzyl)-5'-iodo-1H,1'H-4,4'-bis(1,2,3-triazole) 、 丙烯酸甲酯（MA） 在 palladium diacetate 、 碳酸氢钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以66%的产率得到1-benzyl-1'-(4-tert-butylbenzyl)-5'-(E)-[2-(methoxycarbonyl)-ethenyl]-1H,1'H-4,4'-bi-1,2,3-triazole
  参考文献：
  名称：

  “Click” Synthesis of Nonsymmetrical Bis(1,2,3-triazoles)

  摘要：

  Unsymmetrically 1,1'-disubstituted 4,4'-bis-1H-1,2,3-triazoles 4 have been prepared from 4-ethynyl-1,2,3-triazoles 5 and azides. Following a "double-click" strategy, two complementary approaches were implemented for the preparation of the key 4-ethynyltriazole intermediates 5: (a) the stepwise Swern oxidation/Ohira-Bestman alkynylation of readily available 4-hydroxymethyl-1,2,3-triazoles 8 and (b) the stepwise cycloaddition of TMS-1,4-butadlyne 9. The method is highlighted by its compatibility with orthogonally protected and functionalized saccharide-peptide hybrids and its ability to be extended to the trisubstituted counterparts 12.

  DOI：

  10.1021/ol1003127
• 作为产物：
  描述：

  4-叔丁基苄基叠氮 、 1-benzyl-4-ethynyl-1H-1,2,3-triazole 在 N-溴代丁二酰亚胺(NBS) 、 copper(l) iodide 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以50%的产率得到1-benzyl-1'-(4-tert-butylbenzyl)-5'-iodo-1H,1'H-4,4'-bis(1,2,3-triazole)
  参考文献：
  名称：

  “Click” Synthesis of Nonsymmetrical Bis(1,2,3-triazoles)

  摘要：

  Unsymmetrically 1,1'-disubstituted 4,4'-bis-1H-1,2,3-triazoles 4 have been prepared from 4-ethynyl-1,2,3-triazoles 5 and azides. Following a "double-click" strategy, two complementary approaches were implemented for the preparation of the key 4-ethynyltriazole intermediates 5: (a) the stepwise Swern oxidation/Ohira-Bestman alkynylation of readily available 4-hydroxymethyl-1,2,3-triazoles 8 and (b) the stepwise cycloaddition of TMS-1,4-butadlyne 9. The method is highlighted by its compatibility with orthogonally protected and functionalized saccharide-peptide hybrids and its ability to be extended to the trisubstituted counterparts 12.

  DOI：

  10.1021/ol1003127