1-(4-methoxyphenyl)-3-(1-methylethyl)-4-<1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>azetidin-2-one | 140869-82-5

• 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: 1-(4-methoxyphenyl)-3-(1-methylethyl)-4-<1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>azetidin-2-one
• 英文别名: 1-(4-methoxyphenyl)-3-(1-methylethyl)-4-(1-{[(1,1-dimethylethyl)dimethylsilyl]oxy}ethyl)azetidin-2-one
• CAS: 140869-82-5
• 化学式: C₂₁H₃₅NO₃Si
• 分子量: 377.599
• InChiKey: XOZYSOFAIMTMRA-KFKAGJAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.09
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-(4-methoxyphenyl)-3-(1-methylethyl)-4-<1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>azetidin-2-one 在 ammonium cerium(IV) nitrate 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 (3R,4S)-3-isopropyl-4-<(S)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-2-azetidinone
  参考文献：
  名称：

  Stereoselective synthesis of .beta.-lactams by condensation of titanium enolates of 2-pyridyl thioesters with imines

  摘要：

  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.

  DOI：

  10.1021/jo00041a019
• 作为产物：
  描述：

  (S)-2-(叔丁基-二甲基-锡氧基)-丙醛 在 四氯化钛 、 magnesium sulfate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 1-(4-methoxyphenyl)-3-(1-methylethyl)-4-<1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>azetidin-2-one
  参考文献：
  名称：

  Synthesis of β-lactams by condensation of titanium enolates of 2-pyridylthioesters with imines. Influence of the imine structure on the trans/cis stereoselectivity

  摘要：

  The condensation of the titanium enolates of C-2 alkyl substituted 2-pyridylthioesters with imines affords beta-lactams in trans/cis ratios that largely depend on the structure of the C-imine residue. Bulky and non-chelating heteroatom-containing groups lead to the formation of trans p-lactams, while sterically non-requiring or chelating groups favour the formation of the cia-products. On the basis of NMR evidences a rationale is proposed to account for the observed stereoselectivity.

  DOI：

  10.1016/s0040-4020(01)87005-8