E-3-Ethylidene-4-(methoxycarbonyl)-1-(4-methoxyphenyl)azetidin-2-one | 131533-35-2

• 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: E-3-Ethylidene-4-(methoxycarbonyl)-1-(4-methoxyphenyl)azetidin-2-one
• 英文别名: (E)-1-p-anisyl-3-ethylidene-4-carbomethoxy-2-azetidinone；methyl (3E)-3-ethylidene-1-(4-methoxyphenyl)-4-oxoazetidine-2-carboxylate
• CAS: 131533-35-2
• 化学式: C₁₄H₁₅NO₄
• 分子量: 261.277
• InChiKey: OHMSNZAZNOSXGY-NYYWCZLTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.53
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  dimethyl(phenyl)silyllithium 、 E-3-Ethylidene-4-(methoxycarbonyl)-1-(4-methoxyphenyl)azetidin-2-one 在 CuCN 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 (2S,3S)-3-[(S)-1-(Dimethyl-phenyl-silanyl)-ethyl]-1-(4-methoxy-phenyl)-4-oxo-azetidine-2-carboxylic acid methyl ester 、 anti,cis-3-<1'-(dimethylphenylsilyl)ethyl>-4-(methoxycarbonyl)-1-(p-methoxyphenyl)azetidin-2-one
  参考文献：
  名称：

  Preparation of 3-alkyl .beta.-lactams via the ketene imine cycloaddition reaction using .alpha.-(phenylthio)alkanoyl halides as starting materials: application to the synthesis of (.+-.)-carbapenem building blocks and related compounds

  摘要：

  Preparation of appropriately substituted 3-alkyl beta-lactams via the ketene (or equivalent)-imine cycloaddition reaction is described. The dehydrochlorination reaction of alpha-(phenylthio)alkanoyl chlorides with triethylamine in the presence of imines derived from cinnamaldehydes and p-anisidine produced a high-yield formation of alpha-phenylthio beta-lactams, which upon desulfuration furnished a variety of 3-alkyl beta-lactams in a highly stereoselective fashion. In contrast, reaction between alpha-haloalkanoyl chlorides and cinnamylideneamines in the presence of triethylamine furnished the corresponding [4 + 2] cycloadducts as main products. Preparation of highly functionalized alpha-alkylidene beta-lactams through thermal decomposition of the corresponding beta-lactam sulfoxides or by cycloaddition of alpha,beta-unsaturated acid chlorides to imino esters in the presence of triethylamine is also described. Addition of Flemming's silylcuprate reagent to alpha-alkylidene beta-lactams furnished the corresponding 3-(1'-(dimethylphenylsilyl(ethyl) beta-lactams as (+/-)-thienamycin intermediates.

  DOI：

  10.1021/jo00014a017
• 作为产物：
  描述：

  methyl 3-(benzenesulfinyl)-3-ethyl-1-(4-methoxyphenyl)-4-oxoazetidine-2-carboxylate 以28%的产率得到
  参考文献：
  名称：

  PALOMO, CLAUDIO;COSSIO, FERNANDO P.;ODIZOLA, JOSE M.;OIARBIDE, MIKEL;ONTO+, J. ORG. CHEM., 56,(1991) N4, C. 4418-4428

  摘要：

  DOI：

文献信息

• Formation of 3-[1'-(dimethylphenylsilyl)ethyl]azetidin-2-ones: stereocontrolled formal approach to (.+-.)-thienamycin and (.+-.)-.beta.-(hydroxyalkyl)aspartic acid derivatives
  作者：Claudio Palomo、Jesus M. Aizpurua、Raquel Urchegui、Miren Iturburu

  DOI：10.1021/jo00031a044

  日期：1992.2

  Reaction between (+/-)-beta-(dimethylphenylsilyl)alkanoyl chlorides and imines of glyoxylic esters provided a route to (+/-)-cis-3-[1'-(dimethylphenylsilyl)ethyl]-4-alkoxycarbonyl beta-lactams, while addition of the Fleming's silylcuprate reagent to methyl crotonate and further enolate trapping by the above imines furnished the corresponding (+/-)-trans-3-[1'-(dimethylphenylsilyl)ethyl]-4-alkoxycarbonyl beta-lactams. These beta-lactams, upon appropriate chemical manipulations, provided a stereocontrolled route to (+/-)-thienamycin precursors and (+/-)-beta-(hydroxyalkyl)aspartic acid derivatives.
• PALOMO, CLAUDIO;AIZPURUA, JESUS M.;URCHEGUI, RAQUEL, J. CHEM. SOC. CHEM. COMMUN.,(1990) N0, C. 1390-1392
  作者：PALOMO, CLAUDIO、AIZPURUA, JESUS M.、URCHEGUI, RAQUEL

  DOI：——

  日期：——