1-benzyl-1'-(4-tert-butylbenzyl)-5'-(E)-[2-(methoxycarbonyl)-ethenyl]-1H,1'H-4,4'-bi-1,2,3-triazole | 1218787-73-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-benzyl-1'-(4-tert-butylbenzyl)-5'-(E)-[2-(methoxycarbonyl)-ethenyl]-1H,1'H-4,4'-bi-1,2,3-triazole
• 英文别名: methyl (E)-3-[5-(1-benzyltriazol-4-yl)-3-[(4-tert-butylphenyl)methyl]triazol-4-yl]prop-2-enoate
• CAS: 1218787-73-5
• 化学式: C₂₆H₂₈N₆O₂
• 分子量: 456.547
• InChiKey: GRUNHVRBEZAAKW-CCEZHUSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  87.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  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

文献信息

• “Click” Synthesis of Nonsymmetrical Bis(1,2,3-triazoles)
  作者：Jesus M. Aizpurua、Itxaso Azcune、Raluca M. Fratila、Eva Balentova、Maialen Sagartzazu-Aizpurua、Jose I. Miranda

  DOI：10.1021/ol1003127

  日期：2010.4.2

  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.