2-（3-羟基-1-苯基丙基）-4-（羟甲基）苯酚 | 1312416-97-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-（3-羟基-1-苯基丙基）-4-（羟甲基）苯酚
• 英文名称: Benzenepropanol, 2-hydroxy-5-(hydroxymethyl)-gamma-phenyl-
• 英文别名: 4-(hydroxymethyl)-2-(3-hydroxy-1-phenylpropyl)phenol
• CAS: 1312416-97-9
• 化学式: C₁₆H₁₈O₃
• 分子量: 258.317
• InChiKey: HDFWTWKNWQIGHZ-UHFFFAOYSA-N

物化性质

• 沸点：
  481.9±40.0 °C(Predicted)
• 密度：
  1.216±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-(羟基甲基)-4-苯基苯并二氢吡喃-2-醇 在 magnesium sulfate 、 sodium tetrahydroborate 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 2-（3-羟基-1-苯基丙基）-4-（羟甲基）苯酚
  参考文献：
  名称：

  The Lactol Route to Fesoterodine: An Amine-Promoted Friedel–Crafts Alkylation on Commercial Scale

  摘要：

  We report the discovery and optimization of an amine-promoted Friedel-Crafts alkylation of cinnamaldehyde with 4-hydroxymethyl phenol. This reaction has been used successfully on commercial scale (200 kg) in the context of the manufacture of fesoterodine, a muscarinic antagonist used for the treatment of overactive bladder. Reductive aminations of diisopropylamine and lactol 4 are also discussed, as well as the resolution of the racemic amine rac-2 into its enantiomerically pure form.

  DOI：

  10.1021/op200107g

文献信息

• The Lactol Route to Fesoterodine: An Amine-Promoted Friedel–Crafts Alkylation on Commercial Scale
  作者：Olivier Dirat、Andrew J. Bibb、Colin M. Burns、Graham D. Checksfield、Barry R. Dillon、Stuart E. Field、Steven J. Fussell、Stuart P. Green、Clive Mason、Jinu Mathew、Suju Mathew、Ian B. Moses、Petar I. Nikiforov、Alan J. Pettman、Flavien Susanne

  DOI：10.1021/op200107g

  日期：2011.9.16

  We report the discovery and optimization of an amine-promoted Friedel-Crafts alkylation of cinnamaldehyde with 4-hydroxymethyl phenol. This reaction has been used successfully on commercial scale (200 kg) in the context of the manufacture of fesoterodine, a muscarinic antagonist used for the treatment of overactive bladder. Reductive aminations of diisopropylamine and lactol 4 are also discussed, as well as the resolution of the racemic amine rac-2 into its enantiomerically pure form.