(S)-1-(benzyloxy)-3-(4-phenyl-[1,2,3]triazol-1-yl)propan-2-ol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (S)-1-(benzyloxy)-3-(4-phenyl-[1,2,3]triazol-1-yl)propan-2-ol
• 英文别名: (2S)-1-phenylmethoxy-3-(4-phenyltriazol-1-yl)propan-2-ol
• 化学式: C₁₈H₁₉N₃O₂
• 分子量: 309.368
• InChiKey: RVXUMCJBZRUYAN-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  60.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (S)-苄氧甲基环氧乙烷 、 苯乙炔 在 copper(l) iodide 、 sodium azide 作用下， 以 various solvent(s) 为溶剂， 反应 16.0h， 以91%的产率得到(S)-1-(benzyloxy)-3-(4-phenyl-[1,2,3]triazol-1-yl)propan-2-ol
  参考文献：
  名称：

  Tandem Epoxide or Aziridine Ring Opening by Azide/Copper Catalyzed [3+2] Cycloaddition:  Efficient Synthesis of 1,2,3-Triazolo β-Hydroxy or β-Tosylamino Functionality Motif

  摘要：

  [Graphics]A novel and practical procedure for the synthesis of small molecules possessing beta-hydroxy or N-tosylamino 1,2,3-triazole motif by azidation of epoxides or N-tosylaziridines with sodium azide followed by "click reaction" using eco-friendly PEG-400 as a reaction medium in the presence of 5 mol % of CuI is described. Enantiomerically pure epoxide and N-tosylaziridines were afforded in high yield with excellent ee values maintaining complete stereospecificity.

  DOI：

  10.1021/jo701724f

文献信息

• Tandem Epoxide or Aziridine Ring Opening by Azide/Copper Catalyzed [3+2] Cycloaddition:  Efficient Synthesis of 1,2,3-Triazolo β-Hydroxy or β-Tosylamino Functionality Motif
  作者：Gullapalli Kumaraswamy、Kukkadapu Ankamma、Arigala Pitchaiah

  DOI：10.1021/jo701724f

  日期：2007.12.1

  [Graphics]A novel and practical procedure for the synthesis of small molecules possessing beta-hydroxy or N-tosylamino 1,2,3-triazole motif by azidation of epoxides or N-tosylaziridines with sodium azide followed by "click reaction" using eco-friendly PEG-400 as a reaction medium in the presence of 5 mol % of CuI is described. Enantiomerically pure epoxide and N-tosylaziridines were afforded in high yield with excellent ee values maintaining complete stereospecificity.