2-phenyl-4-(D-threo-O-1',2'-isopropylidene-3'-hydroxypropyl)-2H-1,2,3-triazole | 426260-72-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-phenyl-4-(D-threo-O-1',2'-isopropylidene-3'-hydroxypropyl)-2H-1,2,3-triazole
• CAS: 426260-72-2
• 化学式: C₁₄H₁₇N₃O₃
• 分子量: 275.307
• InChiKey: SEQADUNYDKKNQU-CHWSQXEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.45
• 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：
  0.43
• 拓扑面积：
  69.4
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-phenyl-4-(D-threo-O-1',2'-isopropylidene-3'-hydroxypropyl)-2H-1,2,3-triazole 在 溶剂黄146 作用下， 反应 2.0h， 以60%的产率得到2-phenyl-4-(D-threo-1',2',3'-trihydroxypropyl)-2H-1,2,3-triazole
  参考文献：
  名称：

  Novel Lipase-Catalysed Highly Selective Acetylation Studies on d-Arabino- and d-Threo-polyhydroxyalkyltriazoles

  摘要：

  Five 2-phenyl-4-(D-arabino-4'-cycloamino-3-hydroxy-O-1',2'-isopropylidene-butyl)-2H-1,2,3-triazoles. acyclonucleosides containing unnatural bases have been synthesised by opening of the epoxide ring of 2-phenyl-4-(D-arabino-3',4'-epoxy-O-1',2'-isopropylidenebutyl)-2H-1,2.3-triazole with the corresponding cyclic amines in 70-85% yields. The starting arabino-epoxytriazole was prepared in five steps starting from D-glucose in an overall yield of 15%. All the five triazolylacyclonucleosides were unambiguously identified on the basis of their spectral data. The Structure of one of the intermediates. that is 2-phenyl-4-(D-arabino-1',2',3',4'-tetrahydroxybutyl)-2H-1,2.3-triazole was confirmed by its X-ray crystallographic studies. These acyclonucleosides were subjected to antiviral activity evaluation in CEM-SS cell-based anti HIV assay with the lymphocytropic virus strains HIV-1(IIIB) and HIV-1(RF). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00350-9
• 作为产物：
  描述：

  2-phenyl-4-(D-arabino-1',2',3',4'-tetrahydroxybutyl)-2H-1,2,3-triazole 在 sodium tetrahydroborate 、 sodium periodate 、 三氯化铁 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 14.0h， 生成 2-phenyl-4-(D-threo-O-1',2'-isopropylidene-3'-hydroxypropyl)-2H-1,2,3-triazole
  参考文献：
  名称：

  Novel Lipase-Catalysed Highly Selective Acetylation Studies on d-Arabino- and d-Threo-polyhydroxyalkyltriazoles

  摘要：

  Five 2-phenyl-4-(D-arabino-4'-cycloamino-3-hydroxy-O-1',2'-isopropylidene-butyl)-2H-1,2,3-triazoles. acyclonucleosides containing unnatural bases have been synthesised by opening of the epoxide ring of 2-phenyl-4-(D-arabino-3',4'-epoxy-O-1',2'-isopropylidenebutyl)-2H-1,2.3-triazole with the corresponding cyclic amines in 70-85% yields. The starting arabino-epoxytriazole was prepared in five steps starting from D-glucose in an overall yield of 15%. All the five triazolylacyclonucleosides were unambiguously identified on the basis of their spectral data. The Structure of one of the intermediates. that is 2-phenyl-4-(D-arabino-1',2',3',4'-tetrahydroxybutyl)-2H-1,2.3-triazole was confirmed by its X-ray crystallographic studies. These acyclonucleosides were subjected to antiviral activity evaluation in CEM-SS cell-based anti HIV assay with the lymphocytropic virus strains HIV-1(IIIB) and HIV-1(RF). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00350-9