4-(2,5-anhydro-D-manno-pentitol-1-yl)-2-phenyl-2H-1,2,3-triazole | 210108-61-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(2,5-anhydro-D-manno-pentitol-1-yl)-2-phenyl-2H-1,2,3-triazole
• CAS: 210108-61-5
• 化学式: C₁₃H₁₅N₃O₄
• 分子量: 277.28
• InChiKey: NWKCPZUORZBNJM-FDYHWXHSSA-N

物化性质

• 熔点：
  176-177 °C
• 沸点：
  569.2±60.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.58
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  100.63
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  4-(2,5-anhydro-D-manno-pentitol-1-yl)-2-phenyl-2H-1,2,3-triazole 在 吡啶 、 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 反应 17.0h， 生成 4-(1-O-acetyl-2,5-anhydro-3,4-O-isopropylidene-D-manno-pentitol-1-yl)-2-phenyl-2H-1,2,3-triazole
  参考文献：
  名称：

  Homo-C-Nucleoside Analogs† II. Synthesis and Anomeric Configuration of 4-(2,5-Anhydro-D-Gluco-PEntitol-1-YL)-2-Phenyl2H-1,2,3-Triazole††

  摘要：

  Treatment of 4-(D-gluco-pentitol-1-yl)-2-phenyl-2H-1,2,3-triazole (1) with p-toluenesulfonyl chloride in pyridine solution, afforded the homo-C-nucleoside analog, 4-(2,5-anhydro-D-gluco-pentitol-1-yl)-2-phenyl-2H-1,2,3-triazole (2) as well as its partial p-toluenesulfonyl derivative (3). 4-(5-Chloro-5-deoxy-D-gluco-pentitol-1-yl)2-phenyl-2H-1,2,3-triazole (8), was isolated as a byproduct from the reaction. The structure and anomeric configuration of 2 was determined by acylation, H-1, C-13 NMR, and NOE, spectroscopy as well as mass spectrometry.

  DOI：

  10.1080/07328319808004234
• 作为产物：
  描述：

  4-(D-manno-pentitol-1-yl)-2-phenyl-2H-1,2,3-triazole 在 吡啶 作用下， 反应 48.0h， 以10%的产率得到4-(5-chloro-5-deoxy-D-manno-pentitol-1-yl)-2-phenyl-2H-1,2,3-triazole
  参考文献：
  名称：

  Homo-C-nucleoside analogs III. Studies on the base-catalyzed dehydrative cyclization of 4-(d-manno-pentitol-1-yl)-2-phenyl-2H-1,2,3-triazole

  摘要：

  Treatment of 4-(D-manno-pentitol-1-yl)-2-phenyl-2H-1,2,3-triazole with one molar equivalent of 2,4,6-triisopropylbenzenesulfonyl chloride (TIBSCl) in pyridine solution afforded the homo-C-nucleoside analog; 4-(2,5-anhydro-D-manno-pentitol-1-yl)-2-phenyl-2H-1,2,3-triazole in 54% yield and 4-(alpha-D-arabinopyranosyl)-2-phenyl-2H1,2,3-triazole analog in 3% yield. The 4-(5-O-triisopropylbenzenesulfonyl)-D-manno-pentitol-1-yl)-2-phenyl-2H-1,2,3-triazole analog was isolated as an intermediate and identified as its tetra-O-acetyl derivative. The 4-(5-chloro-5-deoxy-D-manno-pentitol-1-yl)-2-phenyl-2H-1,2,3-triazole analog was isolated as a byproduct. The structure and anomeric configuration of the products were determined by acylation, NMR spectroscopy, and mass spectrometry. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.06.014