(R)-1,2-di(furan-3-yl)-2-hydroxyethanone | 915792-22-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-1,2-di(furan-3-yl)-2-hydroxyethanone
• 英文别名: (2R)-1,2-Di-3-furanyl-2-hydroxyethanone；(2R)-1,2-bis(furan-3-yl)-2-hydroxyethanone
• CAS: 915792-22-2
• 化学式: C₁₀H₈O₄
• 分子量: 192.171
• InChiKey: MTSVJIHGNXJKLC-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-糠醛 在 PVA entrapped benzaldehyde lyase from P_. fluorescens 、 焦磷酸硫胺素 、 magnesium sulfate 作用下， 以 正己烷 、 水 为溶剂， 反应 20.0h， 生成 (R)-1,2-di(furan-3-yl)-2-hydroxyethanone 、 (S)-1,2-di(furan-3-yl)-2-hydroxyethanone
  参考文献：
  名称：

  Stereoselective synthesis of novel benzoins catalysed by benzaldehyde lyase in a gel-stabilised two-phase system

  摘要：

  Asymmetric benzoin condensation was performed using recombinant benzaldehyde lyase (BAL) from Pseudomonas fluorescens Biovar I. To enable the conversion of hydrophobic substrates, the enzyme was entrapped in polyvinyl alcohol and suspended in hexane. Compared to the reported application of the biocatalyst in an aqueous phase containing 20% DMSO, the productivity of the resulting gel-stabilised two-phase system was 3-fold better. The entrapment process had an efficiency of > 90%, no enzyme or cofactor was lost during reaction or storage. The entrapped enzyme was stable in hexane for 1 week at 4 degrees C and more than 1 month at -20 degrees C. Without preceding optimisation the novel benzoins (R)-1,2-di(3-furanyl)-2-hydroxyethanone, (R)-2-hydroxy-1,2-di(3-thienyl) ethanone, (R)-1,2-di(4-ethoxyphenyl)-2-hydroxyethanone, (R)-1,2-di(3-ethoxyphenyl)-2-hydroxyethanone, (R)-2-hydroxy-1,2-di(3-tolyl)ethanone, and (R)-1,2-di(benzofuran-2-yl)-2-hydroxyethanone were prepared with yields up to 31.8% and enantiomeric excess > 99%. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.05.082