(S)-1-(3,4-difluorophenoxy)-3-(4-(methylamino)piperidin-1-yl)propan-2-ol | 1425504-51-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (S)-1-(3,4-difluorophenoxy)-3-(4-(methylamino)piperidin-1-yl)propan-2-ol
• 英文别名: (2S)-1-(3,4-difluorophenoxy)-3-[4-(methylamino)piperidin-1-yl]propan-2-ol
• CAS: 1425504-51-3
• 化学式: C₁₅H₂₂F₂N₂O₂
• 分子量: 300.349
• InChiKey: MTDLMGIYWYDXGQ-LBPRGKRZSA-N

物化性质

• 沸点：
  429.4±45.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  44.7
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-氯苯并噻唑 、 (S)-1-(3,4-difluorophenoxy)-3-(4-(methylamino)piperidin-1-yl)propan-2-ol 以 水 为溶剂， 反应 0.5h， 以83%的产率得到(2S)-1-[4-(1,3-苯并噻唑-2-基-甲基氨基)哌啶-1-基]-3-(3,4-二氟苯氧基)丙-2-醇
  参考文献：
  名称：

  Protecting group-Free Concise Synthesis of (RS)/(S)-Lubeluzole

  摘要：

  Three new, concise, and protecting group-free synthetic routes for (RS)- and (S)-lubeluzole are reported in higher (46-62%) overall yields compared to the reported procedures (6-35%). The key steps involve C-N bond formation via epoxide aminolysis and nucleophilic substitution of 2-chlorobenzothiazole with suitably designed precursor amines and are performed in aqueous medium. Water offers an advantage in promoting the reactions compared to organic solvents and its role Is envisaged as hydrogen-bond mediated electrophile-nucleophile dual activation.

  DOI：

  10.1021/ol302601b
• 作为产物：
  描述：

  4-哌啶酮 在 titanium(IV) isopropylate 、 三乙胺 作用下， 以 乙醇 、 水 为溶剂， 反应 22.0h， 生成 (S)-1-(3,4-difluorophenoxy)-3-(4-(methylamino)piperidin-1-yl)propan-2-ol
  参考文献：
  名称：

  Protecting group-Free Concise Synthesis of (RS)/(S)-Lubeluzole

  摘要：

  Three new, concise, and protecting group-free synthetic routes for (RS)- and (S)-lubeluzole are reported in higher (46-62%) overall yields compared to the reported procedures (6-35%). The key steps involve C-N bond formation via epoxide aminolysis and nucleophilic substitution of 2-chlorobenzothiazole with suitably designed precursor amines and are performed in aqueous medium. Water offers an advantage in promoting the reactions compared to organic solvents and its role Is envisaged as hydrogen-bond mediated electrophile-nucleophile dual activation.

  DOI：

  10.1021/ol302601b

文献信息

• Org Lett 2013, 15, 1158-1161. support infor
  作者：

  DOI：——

  日期：——
• Org Lett 2013, 15, 1158-1161
  作者：

  DOI：——

  日期：——
• Protecting group-Free Concise Synthesis of (<i>RS</i>)/(<i>S</i>)-Lubeluzole
  作者：Damodara N. Kommi、Dinesh Kumar、Kapileswar Seth、Asit K. Chakraborti

  DOI：10.1021/ol302601b

  日期：2013.3.15

  Three new, concise, and protecting group-free synthetic routes for (RS)- and (S)-lubeluzole are reported in higher (46-62%) overall yields compared to the reported procedures (6-35%). The key steps involve C-N bond formation via epoxide aminolysis and nucleophilic substitution of 2-chlorobenzothiazole with suitably designed precursor amines and are performed in aqueous medium. Water offers an advantage in promoting the reactions compared to organic solvents and its role Is envisaged as hydrogen-bond mediated electrophile-nucleophile dual activation.