1-O-[2-(but-2-ynoyl)ethyl]-D-glucopyranose | 1228048-68-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-[2-(but-2-ynoyl)ethyl]-D-glucopyranose
• CAS: 1228048-68-7
• 化学式: C₁₂H₁₈O₈
• 分子量: 290.27
• InChiKey: SRDWHUHBYQOTKH-AZMJIDJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.63
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  125.68
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1-O-[2-(but-2-ynoyl)ethyl]-D-glucopyranose 在 [,14-bis(diphenylphosphino)butane] (1,5-cyclooctadiene)rhodium(I) tetrafluoroborate 、 氢气 作用下， 以 氘代丙酮 、 氘代甲醇 为溶剂， 生成 1-O-[2-(cis-but-2-enoyl)ethyl]-β-D-glucopyranose 、 1-O-[2-(cis-but-2-enoyl)ethyl]-α-D-glucopyranose
  参考文献：
  名称：

  Para-hydrogenated Glucose Derivatives as Potential ¹³C-Hyperpolarized Probes for Magnetic Resonance Imaging

  摘要：

  A set of molecules in which a glucose moiety is bound to a hydrogenable synthon has been synthesized and evaluated for hydrogenation reactions and for the corresponding para-hydrogen-induced polarization (PHIP) effects, in order to select suitable candidates for an in vivo magnetic resonance imaging (MRI) method for the assessment of glucose cellular uptake. It has been found that amidic derivatives do not yield any polarization enhancement, probably due to singlet-triplet state mixing along the reaction pathway. In contrast, ester derivatives are hydrogenated in high yield and afford enhanced H-1 and C-13 NMR spectra after para-hydrogenation. The obtained PHIP patterns are discussed and explained on the basis of the calculated spin level populations in the para-hydrogenated products. These molecules may find interesting applications in C-13 MRI as hyperpolarized probes for assessing the activity of glucose transporters in cells.

  DOI：

  10.1021/ja101399q