(3S)-1-[tert-butyl(dimethyl)silyl]dodec-1-yn-3-ol | 1440569-83-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S)-1-[tert-butyl(dimethyl)silyl]dodec-1-yn-3-ol
• CAS: 1440569-83-4
• 化学式: C₁₈H₃₆OSi
• 分子量: 296.569
• InChiKey: NSPIHSJUXHOEJW-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.54
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (3S)-1-[tert-butyl(dimethyl)silyl]dodec-1-yn-3-ol 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 (S)-dodec-1-yn-3-ol 、 (R)-(+)-1-dodecyn-3-ol
  参考文献：
  名称：

  Asymmetric Hydrogenation of Alkynyl Ketones with the η⁶-Arene/TsDPEN–Ruthenium(II) Catalyst

  摘要：

  Enantioselective hydrogenation of alkynyl ketones catalyzed by Ru(OTf)(TsDPEN)(eta(6)-p-cymene) (TsDPEN = N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine) affords the propargylic alcohols in up to 97% ee. The alkynyl moieties are left intact In most cases. The reaction can be conducted with a substrate-to-catalyst molar ratio as high as 5000 under 10 atm of H-2. The mode of enantioselection is elucidated with the transition state models directed by the CH/pi attractive interaction between the substrate and the catalytic species.

  DOI：

  10.1021/ol4012184
• 作为产物：
  描述：

  1-(tert-butyldimethylsilyl)-1-dodecyn-3-one 在 Ru(OTf)(TsDPEN)(η6-p-cymene) 作用下， 以 甲醇 为溶剂， 50.0 ℃ 、2.0 MPa 条件下， 反应 15.0h， 以94%的产率得到(3S)-1-[tert-butyl(dimethyl)silyl]dodec-1-yn-3-ol
  参考文献：
  名称：

  Asymmetric Hydrogenation of Alkynyl Ketones with the η⁶-Arene/TsDPEN–Ruthenium(II) Catalyst

  摘要：

  Enantioselective hydrogenation of alkynyl ketones catalyzed by Ru(OTf)(TsDPEN)(eta(6)-p-cymene) (TsDPEN = N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine) affords the propargylic alcohols in up to 97% ee. The alkynyl moieties are left intact In most cases. The reaction can be conducted with a substrate-to-catalyst molar ratio as high as 5000 under 10 atm of H-2. The mode of enantioselection is elucidated with the transition state models directed by the CH/pi attractive interaction between the substrate and the catalytic species.

  DOI：

  10.1021/ol4012184