1-(4-methoxyphenyl)-3-ethyl-4-<1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>azetidin-2-one | 135508-44-0

• 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-ethyl-4-<1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>azetidin-2-one
• 英文别名: 1-(4-methoxyphenyl)-3-ethyl-4-(1-{[(1,1-dimethylethyl)dimethylsilyl]oxy}ethyl)azetidin-2-one；(3R,4S)-4-[(1S)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-3-ethyl-1-(4-methoxyphenyl)azetidin-2-one
• CAS: 135508-44-0
• 化学式: C₂₀H₃₃NO₃Si
• 分子量: 363.572
• InChiKey: WRGANHHZQLHTST-BMGDILEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.85
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 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-ethyl-4-<1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>azetidin-2-one 在 (Cl₃CO)2CO-DMSO 、 四丁基氟化铵 、 三乙胺 作用下， 生成 (3R,4S)-4-acetyl-3-ethyl-1-p-methoxyphenyl-2-azetidinone
  参考文献：
  名称：

  Palomo, Claudio; Cossio, Fernando P.; Cuevas, Carmen, Bulletin des Societes Chimiques Belges, 1992, vol. 101, # 7, p. 541 - 554

  摘要：

  DOI：
• 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， 反应 5.08h， 生成 1-(4-methoxyphenyl)-3-ethyl-4-<1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>azetidin-2-one
  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

文献信息

• Preparation of chiral 3-unsubstituted β-lactams from 3-hydroxy β-lactams by using the alkoxyketene-imine cycloaddition reaction as an approach to the azetidinone ring: A formal synthesis of the carbapenem antibiotic (+)-PS-5.
  作者：Claudio Palomo、Fernando P. Cossío、Jesús M. Ontoria、José M. Odriozola

  DOI：10.1016/0040-4039(91)80701-7

  日期：1991.6

  Formation of chiral 3-hydroxy β-lactams from the alkoxyketene-imine cycloaddition reaction followed by deoxygenation under Barton's conditions provided a simple roam to optically active 3-unsubstituted β-lactams.

  由烷氧基乙烯酮-亚胺环加成反应形成手性3-羟基β-内酰胺，然后在巴顿条件下进行脱氧，为光学活性的3-未取代的β-内酰胺提供了简单的漫游条件。