Z-3-Ethylidene-4-(methoxycarbonyl)-1-(4-methoxyphenyl)azetidin-2-one | 124156-30-5

• 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: Z-3-Ethylidene-4-(methoxycarbonyl)-1-(4-methoxyphenyl)azetidin-2-one
• 英文别名: (Z)-1-p-anisyl-3-ethylidene-4-carbomethoxy-2-azetidinone；1-p-anisyl-3-ethylidene-4-carbomethoxy-2-azetidinone
• CAS: 124156-30-5；124156-31-6；131533-34-1；131533-35-2
• 化学式: C₁₄H₁₅NO₄
• 分子量: 261.277
• InChiKey: OHMSNZAZNOSXGY-UHFFFAOYSA-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：

  Z-3-Ethylidene-4-(methoxycarbonyl)-1-(4-methoxyphenyl)azetidin-2-one 在 platinum on activated charcoal sodium hydroxide 、 ammonium cerium(IV) nitrate 、 氢气 、 溶剂黄146 作用下， 以 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 丙酮 、 乙腈 为溶剂， 25.0~60.0 ℃ 、101.33 kPa 条件下， 反应 0.08h， 生成 4-acetoxy-3-ethyl-azetidin-2-one
  参考文献：
  名称：

  Studies on lactams. Part 84. .beta.-Lactams via .alpha.,.beta.-unsaturated acid chlorides: intermediates for carbapenem antibiotics

  摘要：

  DOI：

  10.1021/jo00289a035
• 作为产物：
  描述：

  顺式-1-(4-甲氧基苯基)-3-乙烯基-4-(甲氧羰基)-2-氮杂环丁酮 在 敌草腈 作用下， 以 苯 为溶剂， 反应 6.0h， 生成 Z-3-Ethylidene-4-(methoxycarbonyl)-1-(4-methoxyphenyl)azetidin-2-one
  参考文献：
  名称：

  Studies on lactams. Part 84. .beta.-Lactams via .alpha.,.beta.-unsaturated acid chlorides: intermediates for carbapenem antibiotics

  摘要：

  DOI：

  10.1021/jo00289a035

文献信息

• 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
  作者：Claudio Palomo、Fernando P. Cossio、Jose M. Odiozola、Mikel Oiarbide、Jesus M. Ontoria

  DOI：10.1021/jo00014a017

  日期：1991.7

  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.
• 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.