(4S)-N-(tert-butyldimethylsilyl)-4-<1-(methyl)vinyl>-azetidin-2-one | 127626-96-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (4S)-N-(tert-butyldimethylsilyl)-4-<1-(methyl)vinyl>-azetidin-2-one
• 英文别名: 1-<(1,1-dimethylethyl)dimethylsilyl>-4-(1-methylethenyl)azetidin-2-one；(4S)-1-[tert-butyl(dimethyl)silyl]-4-prop-1-en-2-ylazetidin-2-one
• CAS: 127626-96-4
• 化学式: C₁₂H₂₃NOSi
• 分子量: 225.406
• InChiKey: KWCHKLALIYSJAC-JTQLQIEISA-N

物化性质

• 沸点：
  255.8±29.0 °C(Predicted)
• 密度：
  0.92±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.17
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (4S)-N-(tert-butyldimethylsilyl)-4-<1-(methyl)vinyl>-azetidin-2-one 在 叔丁基过氧化氢 、 selenium(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以55%的产率得到(4S)-N-(tert-butyldimethylsilyl)-4-<1-(hydroxymethyl)vinyl>-azetidin-2-one
  参考文献：
  名称：

  立体控制1β-甲基硫霉素关键中间体的方法

  摘要：

  已经描述了用于1β-甲基硫代霉素的高级中间体（2）的两种立体控制方法。

  DOI：

  10.1016/s0040-4039(00)94390-9
• 作为产物：
  描述：

  (4S)-N-(tert-butyldimethylsilyl)-4-<1-hydroxy-1-(methyl)ethyl>-azetidin-2-one 在 甲基磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以82%的产率得到(4S)-N-(tert-butyldimethylsilyl)-4-<1-(methyl)vinyl>-azetidin-2-one
  参考文献：
  名称：

  立体控制1β-甲基硫霉素关键中间体的方法

  摘要：

  已经描述了用于1β-甲基硫代霉素的高级中间体（2）的两种立体控制方法。

  DOI：

  10.1016/s0040-4039(00)94390-9

文献信息

• Stereoselective synthesis of .beta.-lactams by condensation of titanium enolates of 2-pyridyl thioesters with imines
  作者：Rita Annunziata、Mauro Cinquini、Franco Cozzi、Pier Giorgio Cozzi

  DOI：10.1021/jo00041a019

  日期：1992.7

  A mild and versatile one-pot synthesis of beta-lactams has been performed by condensation of the easily generated titantium enolates of 2-pyridyl thioesters with imines employing chiral reaction partners. Both imines obtained from enantiomerically pure alkoxy aldehydes and the enolate derived from 3-hydroxybutyrate showed high diastereofacial preferences, efficiently transferring the stereochemical information to the stereocenters of the azetidinone ring. Advanced precursors of (+)-PS-5, (+)-PS-6, thienamycin, and 1-beta-methylthienamycin were prepared to illustrate the potential of this method. A H-1-NMR study of the enolization process and a tentative rationalization of the stereochemical results are presented.
• 1β-Methylthienamycin: Some stereocontrolled approaches towards the key intermediate
  作者：Mukund K Gurjar、Manjunath N Bhanu、Vivek B Khare、Ashok Bhandari、Madhusudhan N Deshmukh、A V Rama Rao

  DOI：10.1016/s0040-4020(01)96165-4

  日期：1991.8

  Two stereocontrolled approaches towards a precursor of 1 beta-methyl-thienamycin, have been accomplished by involving stereospecific hydrogenation of 13 and stereoselective hydroboration oxidation of 9. The latter compounds were obtained from the easily accessible chiral building block 7. The hydroboration-oxidation approach was extended to 18 in which the optically active 1R- (1-hydroxy ethyl) side-chain was incorporated. The highly stereoselective hydroboration-oxidation reaction of 9 is explained by considering Houk's models.