5-(β-D-glucopyranosylsulfanyl)-1,10-phenanthroline | 1335009-49-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(β-D-glucopyranosylsulfanyl)-1,10-phenanthroline
• 英文别名: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(1,10-phenanthrolin-5-ylsulfanyl)oxane-3,4,5-triol
• CAS: 1335009-49-8
• 化学式: C₁₈H₁₈N₂O₅S
• 分子量: 374.417
• InChiKey: PVBHXZUYZSPDPZ-IKGUUIFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  141
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  sodium 1-thio-β-D-glucopyranoside 、 5,6-环氧-5,6-二氢-[1,10]菲咯啉 以 乙醇 为溶剂， 反应 36.0h， 以64%的产率得到5-(β-D-glucopyranosylsulfanyl)-1,10-phenanthroline
  参考文献：
  名称：

  Convenient synthesis of 5-aryl(alkyl)sulfanyl-1,10-phenanthrolines from 5,6-epoxy-5,6-dihydro-1,10-phenanthroline, and their activity towards fungal β-d-glycosidases

  摘要：

  A broad series of novel 5-aryl(alkyl)sulfanyl-1,10-phenanthrolines has been prepared by a new simple procedure: a treatment of the commercially available 5,6-epoxy-5,6-dihydro-1,10-phenanthroline with various thiols in the presence of a base. Other functional groups attached to the thiol allow a use of the products as building blocks in synthesis of versatile ligands and in functionalization of surfaces. The synthesized phenanthrolines showed a moderate ability as activators or inhibitors of fungal beta-D-glucosidases and beta-D-galactosidases. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.07.058