3-(2-ethoxyphenoxy)-2-mesyloxy-3-phenyl-1-propanol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(2-ethoxyphenoxy)-2-mesyloxy-3-phenyl-1-propanol
• 英文别名: [(1R,2S)-1-(2-ethoxyphenoxy)-3-hydroxy-1-phenylpropan-2-yl] methanesulfonate
• 化学式: C₁₈H₂₂O₆S
• 分子量: 366.435
• InChiKey: WOCIBFTUEOPLOI-ZWKOTPCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  90.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(2-ethoxyphenoxy)-2-mesyloxy-3-phenyl-1-propanol 在 ammonium hydroxide 、 potassium tert-butylate 、 三乙胺 、 红铝 、 甲基三丁基氯化铵 、 碳酸二甲酯 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 异丙醇 、 甲苯 、 叔丁醇 为溶剂， 反应 11.75h， 生成 (R,R)-瑞波西汀
  参考文献：
  名称：

  Process Development and Scale-up for (±)-Reboxetine Mesylate

  摘要：

  Redevelopment of the commercial process for the synthesis of (+/-)-reboxetine methanesulfonate is described. An optimized and efficient process for the synthesis of (+/-)-reboxetine starting from cinnamyl alcohol was developed. The redeveloped process minimizes impurity formation and utilizes simplified processing to substantially improve process yield and throughput, and is suitable for the efficient synthesis of multiton quantities of reboxetine.

  DOI：

  10.1021/op7000063
• 作为产物：
  描述：

  3-(2-ethoxyphenoxy)-2-mesyloxy-3-phenyl-1-(trimethylsilyloxy)propane 在 盐酸 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 0.5h， 以0.33 g的产率得到3-(2-ethoxyphenoxy)-2-mesyloxy-3-phenyl-1-propanol
  参考文献：
  名称：

  Process Development and Scale-up for (±)-Reboxetine Mesylate

  摘要：

  Redevelopment of the commercial process for the synthesis of (+/-)-reboxetine methanesulfonate is described. An optimized and efficient process for the synthesis of (+/-)-reboxetine starting from cinnamyl alcohol was developed. The redeveloped process minimizes impurity formation and utilizes simplified processing to substantially improve process yield and throughput, and is suitable for the efficient synthesis of multiton quantities of reboxetine.

  DOI：

  10.1021/op7000063

文献信息

• Process Development and Scale-up for (±)-Reboxetine Mesylate
  作者：Kevin E. Henegar、Cynthia T. Ball、Carolyn M. Horvath、Keith D. Maisto、Sarah E. Mancini

  DOI：10.1021/op7000063

  日期：2007.5.1

  Redevelopment of the commercial process for the synthesis of (+/-)-reboxetine methanesulfonate is described. An optimized and efficient process for the synthesis of (+/-)-reboxetine starting from cinnamyl alcohol was developed. The redeveloped process minimizes impurity formation and utilizes simplified processing to substantially improve process yield and throughput, and is suitable for the efficient synthesis of multiton quantities of reboxetine.