4-(D-manno-pentitol-1-yl)-2-phenyl-2H-1,2,3-triazole | 918412-35-8

• 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-(D-manno-pentitol-1-yl)-2-phenyl-2H-1,2,3-triazole
• 英文别名: (1R)-1-(2-phenyl-2H-[1,2,3]triazol-4-yl)-D-arabitol；(1R)-1-(2-Phenyl-2H-[1,2,3]triazol-4-yl)-D-arabit；(1R,2R,3R,4R)-1-(2-phenyltriazol-4-yl)pentane-1,2,3,4,5-pentol
• CAS: 918412-35-8
• 化学式: C₁₃H₁₇N₃O₅
• 分子量: 295.295
• InChiKey: VHHMUCUXNAQPMW-FDYHWXHSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  132
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 4-(D-manno-pentitol-1-yl)-2-phenyl-2H-1,2,3-triazole 在 吡啶 作用下， 反应 48.0h， 以70 mg的产率得到4-(1,2,3,4,5-penta-O-acetyl-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
• 作为产物：
  描述：

  D-manno-[2]heptosulose-bis-phenylhydrazone 生成 4-(D-manno-pentitol-1-yl)-2-phenyl-2H-1,2,3-triazole
  参考文献：
  名称：

  Ettel; Liebster, Collection of Czechoslovak Chemical Communications, 1949, vol. 14, p. 80,89

  摘要：

  DOI：

文献信息

• The Action of Copper Sulfate on the Phenylosazones of the Sugars. IV. The Phenylosotriazoles of Some Heptoses
  作者：W. T. Haskins、Raymond M. Hann、C. S. Hudson

  DOI：10.1021/ja01197a023

  日期：1947.5