1-(4-methoxyphenyl)-3-ethyl-4-(1,4-dioxaspiro<4.5>dec-2-yl)azetidin-2-one | 141318-16-3

• 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-(1,4-dioxaspiro<4.5>dec-2-yl)azetidin-2-one
• CAS: 141318-16-3
• 化学式: C₂₀H₂₇NO₄
• 分子量: 345.439
• InChiKey: DKWQOEIMQBQTIT-KZNAEPCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.51
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  48.0
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  (R)-1,4-二氧杂螺[4,5]癸烷-2-甲醛 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-(1,4-dioxaspiro<4.5>dec-2-yl)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

• Yb(OTf)₃-Catalyzed One-Pot Synthesis of β-Lactams from Silyl Ketene Thioacetals by a Two- or a Three-Component Reaction
  作者：Rita Annunziata、Mauro Cinquini、Franco Cozzi、Valentina Molteni、Olaf Schupp

  DOI：10.1021/jo960844u

  日期：1996.11.15