quinine (R_S)-tert-butanesulfinate

• 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 (R_S)-tert-butanesulfinate
• 英文别名: [(R)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methyl] (S)-2-methylpropane-2-sulfinate
• 化学式: C₂₄H₃₂N₂O₃S
• 分子量: 428.596
• InChiKey: OHSCDNPNQSVDIH-BVQOWTHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  70.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  quinine (R_S)-tert-butanesulfinate 、 异丙基氯化镁 以 四氢呋喃 、 乙醚 为溶剂， 以91%的产率得到(S)-tert-butyl isopropyl sulfoxide
  参考文献：
  名称：

  New General Sulfinylating Process for Asymmetric Synthesis of Enantiopure Sulfinates and Sulfoxides

  摘要：

  [GRAPHICS]A general process for the efficient synthesis of sulfinyl transfer agents has been developed using cinchona alkaloids quinine and quinidine as chiral auxiliaries. The importance of these new and unique sulfinyl transfer agents is exemplified by the expedient synthesis of several sulfoxides in excellent enantiopurities and high yields.

  DOI：

  10.1021/ol0501020
• 作为产物：
  描述：

  叔丁基氯化镁 、 表奎宁定 在 氯化亚砜 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以91%的产率得到quinine (R_S)-tert-butanesulfinate
  参考文献：
  名称：

  New General Sulfinylating Process for Asymmetric Synthesis of Enantiopure Sulfinates and Sulfoxides

  摘要：

  [GRAPHICS]A general process for the efficient synthesis of sulfinyl transfer agents has been developed using cinchona alkaloids quinine and quinidine as chiral auxiliaries. The importance of these new and unique sulfinyl transfer agents is exemplified by the expedient synthesis of several sulfoxides in excellent enantiopurities and high yields.

  DOI：

  10.1021/ol0501020

文献信息

• Method of Preparing Amine Stereoisomers
  申请人：Han Zhengxu

  公开号：US20080214870A1

  公开（公告）日：2008-09-04

  This invention provides intermediates useful in a method of preparing amine stereoisomers. It also provides a method of preparing sulfoxide and sulfinylamine stereoisomers using certain of the intermediates.

  这项发明提供了在制备胺立体异构体的方法中有用的中间体。它还提供了一种使用某些中间体制备亚砜和亚砜胺立体异构体的方法。
• US7332610B2
  申请人：——

  公开号：US7332610B2

  公开（公告）日：2008-02-19
• New General Sulfinylating Process for Asymmetric Synthesis of Enantiopure Sulfinates and Sulfoxides
  作者：Bruce Z. Lu、Fuqiang Jin、Yongda Zhang、Xinhe Wu、Stephen A. Wald、Chris H. Senanayake

  DOI：10.1021/ol0501020

  日期：2005.4.14

  [GRAPHICS]A general process for the efficient synthesis of sulfinyl transfer agents has been developed using cinchona alkaloids quinine and quinidine as chiral auxiliaries. The importance of these new and unique sulfinyl transfer agents is exemplified by the expedient synthesis of several sulfoxides in excellent enantiopurities and high yields.