3-benzyl-5-methyl-1,3-oxazolidine-2,4-dione | 79658-55-2

• 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-methyl-1,3-oxazolidine-2,4-dione
• 英文别名: 3-benzyl-5-methyl-oxazolidine-2,4-dione；3-benzyl-5-methyloxazolidine-2,4-dione；N-benzyl-5-methyloxazolidine-2,4-dione；3-Benzyl-5-methyl-oxazolidin-2,4-dion
• CAS: 79658-55-2；1016-31-5
• 化学式: C₁₁H₁₁NO₃
• 分子量: 205.213
• InChiKey: XBFXNORSBOKBTO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-甲基-1,3-二噻烷 、 3-benzyl-5-methyl-1,3-oxazolidine-2,4-dione 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以44%的产率得到
  参考文献：
  名称：

  Stereoselective Addition of Grignard Reagents and Lithium Alkyls onto 3,5-Disubstituted-1,3-oxazolidine-2,4-diones

  摘要：

  3-Benzyl-5-methyl-1,3-oxazolidine-3,4-diones react with Grignard reactants and with lithium alkyls to yield 4-substituted 3-benzyl-4-hydroxy-5-methyl-1,3-oxazolidine-2-ones. The reaction is stereoselective and follows Cram's rule.

  DOI：

  10.1080/00397911.2011.609301
• 作为产物：
  描述：

  N-苄基-2-溴丙酰胺 在 氧气 、 高氯酸四乙基铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3-benzyl-5-methyl-1,3-oxazolidine-2,4-dione
  参考文献：
  名称：

  Activation of Carbon Dioxide by Electrogenerated Superoxide Ion:  A New Carboxylating Reagent

  摘要：

  DOI：

  10.1021/jo9512057

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。
• Casadei, Maria Antonietta; Cesa, Stefania; Inesi, Achille, Journal of Chemical Research, Miniprint, 1995, # 5, p. 1064 - 1079
  作者：Casadei, Maria Antonietta、Cesa, Stefania、Inesi, Achille、Moracci, Franco Micheletti

  DOI：——

  日期：——
• N-Acyl and N-sulfonyloxazolidine-2,4-diones are pseudo-irreversible inhibitors of serine proteases
  作者：Ana Bela Santana、Susana D. Lucas、Lídia M. Gonçalves、Henrique F. Correia、Teresa A.F. Cardote、Rita C. Guedes、Jim Iley、Rui Moreira

  DOI：10.1016/j.bmcl.2012.04.093

  日期：2012.6

  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.
• 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
• Some N-Alkyl-2,4-oxazolidinediones and their Anticonvulsant Properties
  作者：M. A. Spielman、Guy M. Everett

  DOI：10.1021/ja01183a040

  日期：1948.3