3-benzyl-5,5-dimethyl-2,4-oxazolidinedione | 100192-61-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 3-benzyl-5,5-dimethyl-2,4-oxazolidinedione
• 英文别名: 3-benzyl-5,5-dimethyloxazolidine-2,4-dione；N-benzyl-5,5-dimethyloxazolidine-2,4-dione；3-benzyl-5,5-dimethyl-oxazolidine-2,4-dione；3-Benzyl-5,5-dimethyl-oxazolidin-2,4-dion；5,5-Dimethyl-3-(phenylmethyl)-2,4-oxazolidinedione；3-benzyl-5,5-dimethyl-1,3-oxazolidine-2,4-dione
• CAS: 100192-61-8
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: ZFJZAKGETLLQQC-UHFFFAOYSA-N

物化性质

• 熔点：
  58-59 °C(Solv: hexane (110-54-3))
• 沸点：
  303.9±35.0 °C(Predicted)
• 密度：
  1.214±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-羟基异丁酸甲酯 、 异氰酸苄酯 在 三乙胺 作用下， 以17%的产率得到3-benzyl-5,5-dimethyl-2,4-oxazolidinedione
  参考文献：
  名称：

  N-Acyl and N-sulfonyloxazolidine-2,4-diones are pseudo-irreversible inhibitors of serine proteases

  摘要：

  The synthesis, inhibitory activity and mode of action of oxazolidine-2,4-diones against porcine pancreatic elastase, here used as a model for human neutrophil elastase, are reported. The nature of N-substitution at the oxazolidine-2,4-dione scaffold has large effect on the inhibitory potency against elastase. N-Acyl and N-sulfonyloxazolidine-2,4-diones emerged as potent pseudo-irreversible inhibitors, displaying high second-order rate constants for PPE inactivation. The title compounds were also shown to be potent inhibitors of human neutrophil elastase (HNE) and proteinase-3, and weak inhibitors of human cathepsin G. The results herein presented show that the oxazolidine-2,4-diones represent a new promising class of serine protease inhibitors. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.093

文献信息

• Electrochemical studies on haloamides. Part XII. Electrosynthesis of oxazolidine-2,4-diones
  作者：Maria Antonietta Casadei、Stefania Cesa、Achille Inesi

  DOI：10.1016/0040-4020(95)00257-9

  日期：1995.5

  Electrogenerated bases promote the carboxylation of NH-protic carboxamides bearing a leaving group at the position 2 to give oxazolidine-2,4-diones. The process is believed to involve acid-base reaction with the substrate, carboxylation of its conjugate base to the corresponding carbamate and ring-closure following intramolecular SN2 reaction. A variety of oxazolidine-2,4-diones, including clinically

  电生成的碱促进在位置2带有离去基团的NH-质子型羧酰胺的羧化反应，生成恶唑烷-2,4-二酮。该过程被认为涉及与基板成相应的氨基甲酸盐和闭环以下的分子内S酸性-碱反应，其共轭碱的羧化Ñ 2反应。已经以高至优异的收率制备了各种恶唑烷-2,4-二酮，包括临床使用的trimethadione®和malidone®，确立了这种新的成环方法的范围和通用性。
• 2(3H)-Oxazolones from α-Hydroxy Amides and Keteneylidenetriphenylphosphorane via a Phoshorus Ylide Cascade
  作者：Jonas Löffler、Rainer Schobert

  DOI：10.1002/jlac.199719970132

  日期：1997.1

  activity”. Evidence for the proposed mechanism is provided by trapping the intermediate ylide species with suitable carbonyl compounds. This technique may also be used to exclusively prepare the 2,4-oxazolidinediones 13 in good yields.

  在二甲苯中加热后，α-羟基酰胺3与累积的磷内鎓盐1反应，以40-80％的收率得到取代的2（3 H）-恶唑酮8。经由加料/环化/反应的进行间分子Wittig烯化序列，这意味着三种不同类型的增加“叶立德活性”的磷叶立德。通过用合适的羰基化合物捕获中间叶立德物质，为提出的机理提供了证据。该技术还可用于以良好的产率专门制备2，4-恶唑烷二酮13。
• N-Substituted Oxazolidinediones
  作者：Seymour L. Shapiro、Ira M. Rose、Frank C. Testa、Eric Roskin、Louis Freedman

  DOI：10.1021/ja01533a042

  日期：1959.12
• Davies et al., Journal of the Chemical Society, 1950, p. 34
  作者：Davies et al.

  DOI：——

  日期：——
• US2559011
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