cis-3-Ethyl-4-(methoxycarbonyl)-1-(4-methoxyphenyl)azetidin-2-one | 124156-23-6

• 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: cis-3-Ethyl-4-(methoxycarbonyl)-1-(4-methoxyphenyl)azetidin-2-one
• 英文别名: cis-3-ethyl-4-methoxycarbonyl-1-(4-methoxyphenyl)azetidin-2-one；cis-1-p-anisyl-3-ethyl-4-carbomethoxy-2-azetidinone；methyl (2S,3S)-3-ethyl-1-(4-methoxyphenyl)-4-oxoazetidine-2-carboxylate
• CAS: 124156-23-6；127055-24-7；127055-25-8
• 化学式: C₁₄H₁₇NO₄
• 分子量: 263.293
• InChiKey: VWPGGFGZYVXXPS-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  cis-3-Ethyl-4-(methoxycarbonyl)-1-(4-methoxyphenyl)azetidin-2-one 在 锂硼氢 、 溴化二甲基溴化锍 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 cis-1-(p-methoxyphenyl)-3-ethyl-4-formyl-2-azetidinone
  参考文献：
  名称：

  酰氯-亚氨基酯缩合：直接接触PS-5和PS-6中间体及相关化合物的方法

  摘要：

  在α-亚氨基酯存在下，用三乙胺对烷酰氯进行脱氯化氢反应，可制得3-烷基-4-烷氧基羰基β-内酰胺，产率高，立体选择性高。

  DOI：

  10.1039/c39900000248
• 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 platinum on activated charcoal 敌草腈 、 氢气 作用下， 以 乙酸乙酯 、 苯 为溶剂， 反应 6.0h， 生成 cis-3-Ethyl-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

• The acid chloride–iminoester condensation: a direct approach to PS-5 and PS-6 intermediates and related compounds
  作者：Claudio Palomo、Jesús Ma. Ontoria、José M. Odriozola、Jesús M. Alzpurua、Iñtaki Ganboa

  DOI：10.1039/c39900000248

  日期：——

  The dehydrochlorination of alkanoyl chlorides with triethylamine in the presence of α-iminoesters produced 3-alkyl-4-alkoxycarbonyl β-lactams in excellent yields and high stereoselectivity.

  在α-亚氨基酯存在下，用三乙胺对烷酰氯进行脱氯化氢反应，可制得3-烷基-4-烷氧基羰基β-内酰胺，产率高，立体选择性高。
• Diastereoselective Conjugate Reduction and Enolate Trapping with Glyoxylate Imines. A Concise Approach to β-Lactams that Involves a Ternary Combination of Components
  作者：Claudio Palomo、Jesús M Aizpurua、Jose Javier Gracenea

  DOI：10.1021/jo981574d

  日期：1999.3.1
• 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.
• Alkyl(phenylthio)ketenes as synthetic equivalents of monoalkylketenes: A concise general route to 3-alkyl β-lactams as carbapenem building-blocks
  作者：Claudio Palomo、Fernando P. Cossío、José M. Odriozola、Mikel Oiarbide、Jesús M. Ontoria

  DOI：10.1016/s0040-4039(01)80749-8

  日期：1989.1
• 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：——