(S,S)-Bis[5-(1,1-dimethylethyl)-2-(1-hydroxypropyl)phenyl] diselenide | 200640-08-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S,S)-Bis[5-(1,1-dimethylethyl)-2-(1-hydroxypropyl)phenyl] diselenide
• 英文别名: (1S)-1-[4-tert-butyl-2-[[5-tert-butyl-2-[(1S)-1-hydroxypropyl]phenyl]diselanyl]phenyl]propan-1-ol
• CAS: 200640-08-0
• 化学式: C₂₆H₃₈O₂Se₂
• 分子量: 540.507
• InChiKey: NIHBBOXEJNFORE-VXKWHMMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.44
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S,S)-Bis[5-(1,1-dimethylethyl)-2-(1-hydroxypropyl)phenyl] diselenide 在 溴 作用下， 以 四氯化碳 、 乙醚 为溶剂， 反应 4.33h， 生成 (S)-1-[4-tert-Butyl-2-((R)-2-methoxy-2-phenyl-ethylselanyl)-phenyl]-propan-1-ol
  参考文献：
  名称：

  Asymmetric Addition Reactions with Optimized Selenium Electrophiles

  摘要：

  AbstractThe synthesis of various nonracemic diselenides by different methods is described. These diselenides are precursors for optically active selenium electrophiles. Their facial selectivity upon addition to styrene was investigated with respect to the chiral moiety neighboring the selenium. Diselenides 1 i, 1 n, and 1 v yielded addition products 7 with diastereomeric excesses up to 95%. Some diselenides, intermediates, and products of the addition reaction were investigated by 77Se NMR spectroscopy.

  DOI：

  10.1002/chem.19970031123
• 作为产物：
  描述：

  (-)-1-[4-(2,2-dimethylethyl)phenyl]propan-1-ol 在 selenium 、 正丁基锂 、 四甲基乙二胺 作用下， 以 正己烷 、 正戊烷 为溶剂， 以42%的产率得到(S,S)-Bis[5-(1,1-dimethylethyl)-2-(1-hydroxypropyl)phenyl] diselenide
  参考文献：
  名称：

  Asymmetric Addition Reactions with Optimized Selenium Electrophiles

  摘要：

  AbstractThe synthesis of various nonracemic diselenides by different methods is described. These diselenides are precursors for optically active selenium electrophiles. Their facial selectivity upon addition to styrene was investigated with respect to the chiral moiety neighboring the selenium. Diselenides 1 i, 1 n, and 1 v yielded addition products 7 with diastereomeric excesses up to 95%. Some diselenides, intermediates, and products of the addition reaction were investigated by 77Se NMR spectroscopy.

  DOI：

  10.1002/chem.19970031123

文献信息

• Asymmetric Addition Reactions with Optimized Selenium Electrophiles
  作者：Thomas Wirth、Gianfranco Fragale

  DOI：10.1002/chem.19970031123

  日期：1997.11

  AbstractThe synthesis of various nonracemic diselenides by different methods is described. These diselenides are precursors for optically active selenium electrophiles. Their facial selectivity upon addition to styrene was investigated with respect to the chiral moiety neighboring the selenium. Diselenides 1 i, 1 n, and 1 v yielded addition products 7 with diastereomeric excesses up to 95%. Some diselenides, intermediates, and products of the addition reaction were investigated by 77Se NMR spectroscopy.