quinine (Rs)-n-butylsulfinate | 1351958-46-7

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 金鸡纳生物碱
• 英文名称: quinine (Rs)-n-butylsulfinate
• CAS: 1351958-46-7
• 化学式: C₂₄H₃₂N₂O₃S
• 分子量: 428.596
• InChiKey: IWUBBTJJDPSFCA-WDKVIVEMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.66
• 重原子数：
  30.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  51.66
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  quinine (Rs)-n-butylsulfinate 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以87%的产率得到butane-1-sulfinamide
  参考文献：
  名称：

  Asymmetric Synthesis of Sulfinamides Using (−)-Quinine as Chiral Auxiliary

  摘要：

  A process has been designed and demonstrated for the asymmetric synthesis of sulfinamides using quinine as auxiliary. A variety of chiral sulfinamides including N-alkyl sulfinamides with diverse structure were prepared in good yields and excellent enantioselectivity starting from easily available and inexpensive reagents. The auxiliary quinine could be recovered and recycled.

  DOI：

  10.1021/jo201825b
• 作为产物：
  描述：

  、 butane,chlorozinc(1+) 以 四氢呋喃 为溶剂， 反应 0.5h， 以5.68 g的产率得到quinine (Rs)-n-butylsulfinate
  参考文献：
  名称：

  Asymmetric Synthesis of Sulfinamides Using (−)-Quinine as Chiral Auxiliary

  摘要：

  A process has been designed and demonstrated for the asymmetric synthesis of sulfinamides using quinine as auxiliary. A variety of chiral sulfinamides including N-alkyl sulfinamides with diverse structure were prepared in good yields and excellent enantioselectivity starting from easily available and inexpensive reagents. The auxiliary quinine could be recovered and recycled.

  DOI：

  10.1021/jo201825b