trans-4-acetoxy-3-ethyl-1-(4-methoxyphenyl)azetidin-2-one | 119067-41-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环丁烷
• 英文名称: trans-4-acetoxy-3-ethyl-1-(4-methoxyphenyl)azetidin-2-one
• 英文别名: trans-4-acetoxy-1-p-anisyl-3-ethylazetidin-2-one；[(2R,3R)-3-ethyl-1-(4-methoxyphenyl)-4-oxoazetidin-2-yl] acetate
• CAS: 119067-41-3
• 化学式: C₁₄H₁₇NO₄
• 分子量: 263.293
• InChiKey: RGCMYTKACSNJMI-GXTWGEPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.96
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  trans-4-acetoxy-3-ethyl-1-(4-methoxyphenyl)azetidin-2-one 以90%的产率得到
  参考文献：
  名称：

  ODRIOZOLA, JOSE M.;COSSIO, FERNANDO P.;PALOMO, CLAUDIO, J. CHEM. SOC. CHEM. COMMUN.,(1988) N 12, 809-810

  摘要：

  DOI：
• 作为产物：
  描述：

  (3S,4R)-4-acetyl-3-ethyl-1-(4-methoxyphenyl)azetidin-2-one 以55%的产率得到
  参考文献：
  名称：

  ODRIOZOLA, JOSE M.;COSSIO, FERNANDO P.;PALOMO, CLAUDIO, J. CHEM. SOC. CHEM. COMMUN.,(1988) N 12, 809-810

  摘要：

  DOI：

文献信息

• A short formal synthesis of the carbapenem antibiotic (±)-PS-5
  作者：José M. Odriozola、Fernando P. Cossío、Claudio Palomo

  DOI：10.1039/c39880000809

  日期：——

  A practical stereoselective synthesis of 4-acetoxy-3-ethylazetidin-2-one via Reformatsky reaction between methyl-α-bromobutyrate and N-4-methoxyphenyl-α-methylcinnamyildeneamine is described.

  描述了通过甲基-α-溴丁酸酯和N -4-甲氧基苯基-α-甲基肉桂亚胺之间的Reformatsky反应的4-乙酰氧基-3-乙基氮杂环丁烷-2-酮的立体选择性合成的实用方法。
• The Reformatskii type reaction of Gilman and Speeter in the preparation of valuable .beta.-lactams in carbapenem synthesis: scope and synthetic utility
  作者：Claudio Palomo、Fernando P. Cossio、Ana Arrieta、Jose M. Odriozola、Mikel Oiarbide、Jesus M. Ontoria

  DOI：10.1021/jo00285a021

  日期：1989.11
• Stereoselective preparation of mono- and bis-.beta.-lactams by the 1,4-diaza-1,3-diene - acid chloride condensation: scope and synthetic applications
  作者：Benito Alcaide、Yolanda Martin-Cantalejo、Javier Perez-Castells、Julian Rodriguez-Lopez、Miguel A. Sierra、Angeles Monge、Virginia Perez-Garcia

  DOI：10.1021/jo00048a027

  日期：1992.10

  The dehydrochlorination of a variety of acid chlorides with triethylamine in the presence of 1,4-diaza 1,3-dienes gives in fair to excellent yields, with total stereoselectivity, cis-4-imino beta-lactams 2, cis-4-formyl beta-lactams 3, or C4,C4'-bis-beta-lactams 4, depending on the reaction conditions. The reaction tolerates a wide variety of substituents, including alkoxy, thiophenoxy, amino, aryl, alkyl, alkylidene, and halogen groups, at the ketene moiety. The synthetic versatility of compounds 3 has been demonstrated by their conversion to intermediates in the synthesis of carbapenems PS-5 and PS-6. Base-induced isomerization of compounds 4 to novel bis-gamma-lactams 5, which in turn are aza analogs of glycaric acids, occurred with total retention of the configuration. This process is formally the elongation of glyoxal in four carbons bearing four contiguous stereocenters with total stereoselectivity in only three or four synthetic steps.