3-(4-{[tert-Butyl(dimethyl)silyl]oxy}phenyl)prop-2-en-1-ol | 143692-99-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: 3-(4-{[tert-Butyl(dimethyl)silyl]oxy}phenyl)prop-2-en-1-ol
• 英文别名: 3-[4-[tert-butyl(dimethyl)silyl]oxyphenyl]prop-2-en-1-ol
• CAS: 143692-99-3
• 化学式: C₁₅H₂₄O₂Si
• 分子量: 264.44
• InChiKey: PCPHHMMSUYZESW-UHFFFAOYSA-N

物化性质

• 沸点：
  340.2±30.0 °C(Predicted)
• 密度：
  0.978±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.08
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  、 3-(4-{[tert-Butyl(dimethyl)silyl]oxy}phenyl)prop-2-en-1-ol 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 C₂₉H₄₂O₁₁Si
  参考文献：
  名称：

  Laccase-catalyzed dimerization of glycosylated lignols

  摘要：

  Phenylpropanoid glucosides (PPGs) are naturally occurring and bioactive phenolic derivatives, largely distributed in plants. In this work different PPGs have been chemically or enzymatically synthesized from the lignols coniferyl and p-coumaryl alcohols as substrates for a lactase-catalyzed oxidative coupling. The biooxidation of these PPGs has been investigated here and novel dihydrobenzofuran-based structurally modified analogues have been isolated and characterized. Specifically, the presence of a carbohydrate moiety increased the water solubility of these compounds and reduced the number of dimeric products, as pinoresinol-like structures could not be formed. Looking for a possible sugar-promoted stereochemical enrichment of the obtained diastereomeric mixtures of dimers, different carbohydrate moieties (D-glucose, L-glucose and the disaccharide rutinose) were considered and the respective d.e. values of the dimeric products were measured by H-1 NMR and HPLC. However, it was found that the sugar substituent had a minor effect on the stereochemical outcome of the radical coupling reactions, the best measured result being a d.e. value of 21%. (C) 2016 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2016.10.019