trans-1-p-anisyl-3-acetyl-4-carbomethoxy-2-azetidinone | 124156-38-3

• 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: trans-1-p-anisyl-3-acetyl-4-carbomethoxy-2-azetidinone
• 英文别名: methyl (2S,3S)-3-acetyl-1-(4-methoxyphenyl)-4-oxoazetidine-2-carboxylate
• CAS: 124156-38-3；124156-37-2；131533-33-0；142436-50-8
• 化学式: C₁₄H₁₅NO₅
• 分子量: 277.277
• InChiKey: LPSUKNJRIKMFHW-NEPJUHHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  trans-1-p-anisyl-3-acetyl-4-carbomethoxy-2-azetidinone 在 palladium on activated charcoal 咪唑 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 ammonium cerium(IV) nitrate 、 三氧化硫 、 四丁基氟化铵 、 氢气 、 三氧化硫吡啶 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 81.0h， 生成 (2S,3S)-2-Acetoxymethyl-3-((R)-1-{2-[2-(2-chloro-acetylamino)-thiazol-4-yl]-2-[(Z)-methoxyimino]-acetoxy}-ethyl)-4-oxo-azetidine-1-sulfonatetetrabutyl-ammonium;
  参考文献：
  名称：

  Synthetic Approach toward the Development of New b-Lactamase Inhibitors

  摘要：

  New racemic thienamonobactams (21) and (28), designed on the basis of hybridization between thienamycin (5) and aztreonam (6), were successfully synthesized by exploiting the [2+2] cycloaddition reaction of diketene with imine (7). Compound (28) exhibited significant inhibitory activity (ID50 = 37 mu M) against Citrobacter freundii cephalosporinase.

  DOI：

  10.3987/com-97-s74
• 作为产物：
  描述：

  cis-1-p-anisyl-3-acetyl-4-carbomethoxy-2-azetidinone 在 敌草腈 作用下， 以 苯 为溶剂， 以83%的产率得到trans-1-p-anisyl-3-acetyl-4-carbomethoxy-2-azetidinone
  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

• A highly stereoselective formal synthesis of (±)-thienamycin through organocopper enolate–iminoester condensation
  作者：Claudio Palomo、Jesus M. Aizpurua、Raquel Urchegui

  DOI：10.1039/c39900001390

  日期：——

  crotonate and enolate trapping by methyl 4-methoxyphenyliminoacetate produced a high yield of (1′S*,3R*,4S)-3-[1-(dimethylphenylsilyl)ethyl]-4-methoxycarbonyl-1-(4-methoxyphenyl)azetidin-2-one as a (±)-thienamycin building block.

  将弗莱明甲硅烷基杯酸酯试剂共轭添加到巴豆酸甲酯中，并通过4-甲氧基苯基亚氨基乙酸甲酯捕获烯醇化物，得到高产率的（1 'S *，3 R *，4 S）-3- [1-（二甲基苯基甲硅烷基）乙基] -4 -甲氧基羰基-1-（4-甲氧基苯基）氮杂环丁烷-2-one作为（±）-噻吩霉素的构建基块。
• 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.
• MANHAS, M. S.;GHOSH, MALAY;BOSE, AJAY K., J. ORG. CHEM., 55,(1990) N, C. 575-580
  作者：MANHAS, M. S.、GHOSH, MALAY、BOSE, AJAY K.

  DOI：——

  日期：——
• 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：——