trans-4-acetoxy-3-isopropylazetidin-2-one | 73660-77-2

• 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: trans-4-acetoxy-3-isopropylazetidin-2-one
• 英文别名: [(2S,3S)-4-oxo-3-propan-2-ylazetidin-2-yl] acetate
• CAS: 73660-77-2
• 化学式: C₈H₁₃NO₃
• 分子量: 171.196
• InChiKey: HPSUIEBVDOKXPY-SVRRBLITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-溴代异戊酸甲酯 在 ammonium cerium(IV) nitrate 、 二甲基硫 、 碘 、 臭氧 、 间氯过氧苯甲酸 、 锌 作用下， 以 水 、 甲苯 、 乙腈 、 苯 为溶剂， 反应 8.0h， 生成 trans-4-acetoxy-3-isopropylazetidin-2-one
  参考文献：
  名称：

  The Reformatskii type reaction of Gilman and Speeter in the preparation of valuable .beta.-lactams in carbapenem synthesis: scope and synthetic utility

  摘要：

  DOI：

  10.1021/jo00285a021

文献信息

• The α-bromoester-imine condensation promoted by zinc-trimethylchlorosilane: a stereospecific short formal synthesis of (±)-carbapenem antibiotics and related compounds
  作者：Fernando P. Cossío、José M. Odriozola、Mikel Oiarbide、Claudio Palomo

  DOI：10.1039/c39890000074

  日期：——

  Ethyl bromoacetate reacts with imines in the presence of zinc activated by trimethylchlorosilane to give high yields of 3-unsubstituted β-lactams.

  在三甲基氯硅烷活化的锌存在下，溴乙酸乙酯与亚胺反应，可高产率生成3-未取代的β-内酰胺。
• COVALENTLY BINDING IMAGING PROBES
  申请人：WENDT Karl-Ulrich

  公开号：US20110059018A1

  公开（公告）日：2011-03-10

  The present invention relates to molecular probes of the formula (I) L1-R1-L-A-X  (I) as defined herein that allow for the observation of the catalytic activity of a selected caspase, cathepsin, MMP and carboxypeptidase in in vitro assays, in cells or in multicellular organisms, a method for their preparation and the use thereof.

  本发明涉及分子探针的公式(I)L1-R1-L-A-X(I)，如在此定义，能够允许在体外测定、细胞或多细胞生物中观察所选的caspase、cathepsin、MMP和carboxypeptidase的催化活性，以及其制备方法和使用方法。
• 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.
• 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