3-hydroxy-2-[5-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]thiophen-2-yl]chromen-4-one | 1190883-40-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3-hydroxy-2-[5-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]thiophen-2-yl]chromen-4-one
• CAS: 1190883-40-9
• 化学式: C₁₈H₁₆O₆S
• 分子量: 360.387
• InChiKey: RLSAEKMBVSCDGB-CYZMBNFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  125
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 以85%的产率得到3-hydroxy-2-[5-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]thiophen-2-yl]chromen-4-one
  参考文献：
  名称：

  Efficient Synthesis of Ratiometric Fluorescent Nucleosides Featuring 3-Hydroxychromone Nucleobases

  摘要：

  The synthesis of a novel class of fluorescent nucleosides featuring 2-aryl-3-hydroxychromones (3-HC) as base analogues is described. Nucleoside la bearing the 2-thienyl-3-HC nucleobase was prepared using sequential aryl-aldol condensation/cycloetherification or a Friedel-Crafts glycosylation as key steps. The synthesis of the triazolyl derivative 1b was achieved using a convergent 1,3-dipolar cycloaddition strategy. Fluorescence studies show that 3-HC-thienyl-nucleoside la displays high sensitivity of its dual emission to polarity changes and therefore is highly promising for nucleic acid labelling. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.07.021