(S_P)-[(1S,2R)-O-(tert-butyldimethylsilyl)isobornyl-10-sulfonamidyl]cyclohexylmethylphenylphosphinimine | 254100-61-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (S_P)-[(1S,2R)-O-(tert-butyldimethylsilyl)isobornyl-10-sulfonamidyl]cyclohexylmethylphenylphosphinimine
• 英文别名: 1-[(1S,2R,4R)-2-[tert-butyl(dimethyl)silyl]oxy-7,7-dimethyl-1-bicyclo[2.2.1]heptanyl]-N-(cyclohexyl-methyl-phenyl-λ5-phosphanylidene)methanesulfonamide
• CAS: 254100-61-3
• 化学式: C₂₉H₅₀NO₃PSSi
• 分子量: 551.846
• InChiKey: LBONTLHTNRPXEA-YBIRMNIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.02
• 重原子数：
  36.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  55.73
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S_P)-[(1S,2R)-O-(tert-butyldimethylsilyl)isobornyl-10-sulfonamidyl]cyclohexylmethylphenylphosphinimine 在 硫酸 作用下， 以 1,4-二氧六环 为溶剂， 以93%的产率得到(R_P*)-cyclohexyl(methyl)phenylphosphine oxide
  参考文献：
  名称：

  A Novel Resolution Procedure for the Preparation of P-Stereogenic Phosphine Oxides

  摘要：

  [GRAPHICS]A new general route for preparing enantiomerically pure P-stereogenic phosphine oxides has been developed by exploiting the Staudinger reaction between racemic tertiary phosphines and an enantiomerically pure organoazide. The resulting phosphinimines are easily resolved by either crystallization or flash chromatography and serve as synthetic intermediates toward enantiomerically pure phosphine oxides.

  DOI：

  10.1021/ol991174s
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 氯化亚砜 、 sodium azide 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基苯胺 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 27.0h， 生成 (S_P)-[(1S,2R)-O-(tert-butyldimethylsilyl)isobornyl-10-sulfonamidyl]cyclohexylmethylphenylphosphinimine
  参考文献：
  名称：

  A Novel Resolution Procedure for the Preparation of P-Stereogenic Phosphine Oxides

  摘要：

  [GRAPHICS]A new general route for preparing enantiomerically pure P-stereogenic phosphine oxides has been developed by exploiting the Staudinger reaction between racemic tertiary phosphines and an enantiomerically pure organoazide. The resulting phosphinimines are easily resolved by either crystallization or flash chromatography and serve as synthetic intermediates toward enantiomerically pure phosphine oxides.

  DOI：

  10.1021/ol991174s

文献信息

• A Simple Resolution Procedure Using the Staudinger Reaction for the Preparation of <i>P</i>-Stereogenic Phosphine Oxides
  作者：Neil G. Andersen、Philip D. Ramsden、Daqing Che、Masood Parvez、Brian A. Keay

  DOI：10.1021/jo015909u

  日期：2001.11.1

  (+/-)-P-stereogenic phosphines is achieved by exploiting the Staudinger reaction of a (+/-)-phosphine with enantiopure (1S,2R)-O-(tert-butyldimethylsilyl)isobornyl-10-sulfonyl azide. The resulting mixtures of diastereomeric phosphinimines are generally separable by fractional crystallization or flash chromatography. Subsequent acid-catalyzed hydrolysis provides the corresponding optically pure phosphine oxides

  通过利用（+/-）膦与对映纯（1S，2R）-O-（叔丁基二甲基甲硅烷基）异冰片基-10的Staudinger反应可实现多种（+/-）-P-立体异构膦的拆分-磺酰叠氮化物。非对映体膦亚胺的所得混合物通常可通过分步结晶或快速色谱分离。随后的酸催化的水解以高收率提供了相应的光学纯的氧化膦。