4-methoxycarbonyl-4-oxazolin-2-one | 3969-02-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-methoxycarbonyl-4-oxazolin-2-one
• 英文别名: 2-oxo-2,3-dihydro-oxazole-4-carboxylic acid methyl ester；4-carbomethoxy-4-oxazolin-2-one；2-oxo-3H-oxazole-4-carboxylic acid methyl ester；methyl 2-oxo-3H-1,3-oxazole-4-carboxylate
• CAS: 3969-02-6
• 化学式: C₅H₅NO₄
• 分子量: 143.099
• InChiKey: PPZSBDRRJQQMLL-UHFFFAOYSA-N

物化性质

• 密度：
  1.414±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-methoxycarbonyl-4-oxazolin-2-one 在 palladium on activated charcoal 氢气 作用下， 反应 1.0h， 生成 3-Acetyl-2-oxo-oxazolidine-4-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of 4-carboethoxy-4-oxazolin-2-ones from 3-nosyloxy-2-ketoesters

  摘要：

  3-Nosyloxy-2-ketoesters, available from 2-ketoesters, react efficiently with methyl carbamate and tosic acid in refluxing toluene to provide 4-carboalkoxy-4-oxazolin-2-ones in good yields (41-84%). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10854-1
• 作为产物：
  描述：

  Methyl 2,3-diacetyloxy-2-(methoxycarbonylamino)propanoate 在 甲醇 、 potassium carbonate 作用下， 反应 1.5h， 以78%的产率得到4-methoxycarbonyl-4-oxazolin-2-one
  参考文献：
  名称：

  Oxidation of didehydro-α-amino acids as a route to β-hydroxy-or β-amino-pyruvic derivatives and to α-acylglycinates

  摘要：

  Oxidation of protected didehydro-alpha-amino acids with N-bromosuccinimide or lead tetraacetate affords imines of beta-bromo- or beta-acetoxy-pyruvates. The hydrolysis of brominated imines proceeds through addition of water followed by intramolecular displacement of bromine, According to experimental procedures, intermediate hydroxyaziridines, hydroxyoxazolines or aminoepoxides have to be considered. Two pathways are examined for hydrolysis of beta-acetoxyimines: cyclisation to oxazolones or conversion to acylglycinates when imines are converted to the isomeric enamines prior to deprotection.

  DOI：

  10.1039/p19960001833

文献信息

• Huisgen,R.; Blaschke,H., Chemische Berichte, 1965, vol. 98, p. 2985 - 2997
  作者：Huisgen,R.、Blaschke,H.

  DOI：——

  日期：——
• Synthesis of 2-Oxazolone-4-carboxylates from 3-Nosyloxy- and 3-Bromo-2-ketoesters
  作者：John F. Okonya、Robert V. Hoffman、M. Catherine Johnson

  DOI：10.1021/jo010630z

  日期：2002.2.1

  New methods for the synthesis of 2-oxazolone-4-carboxylates from 3-nosyloxy- and 3-bromo-2-ketoesters are described. Condensation of 3-nosyloxy-2-ketoesters with methyl carbamate in refluxing toluene in the presence of p-TSA provided 2-oxazolone-4-carboxylates in good yields (41-80%). Alternatively, bromination of alpha-ketoesters with CuBr2 provided 3-bromo-2-ketoesters which condensed with methyl carbamate in the presence of p-TSA and AgOTf under similar conditions to provide 2-oxazolone-4-carboxylates in comparable yields (30-79%). The 2-oxazolone-4-carboxylates bear functionality that can be elaborated to a variety of potentially useful compounds. For example, some of these heterocycles were readily N-acylated, reduced to alcohols, or saponified and coupled with amino acids.
• WO2006/110477
  申请人：——

  公开号：——

  公开（公告）日：——
• Oxidation of didehydro-α-amino acids as a route to β-hydroxy-or β-amino-pyruvic derivatives and to α-acylglycinates
  作者：Benoît Miossec、Hélène Rudyk、Loïc Toupet、Renée Danion-Bougot、Daniel Danion

  DOI：10.1039/p19960001833

  日期：——

  Oxidation of protected didehydro-alpha-amino acids with N-bromosuccinimide or lead tetraacetate affords imines of beta-bromo- or beta-acetoxy-pyruvates. The hydrolysis of brominated imines proceeds through addition of water followed by intramolecular displacement of bromine, According to experimental procedures, intermediate hydroxyaziridines, hydroxyoxazolines or aminoepoxides have to be considered. Two pathways are examined for hydrolysis of beta-acetoxyimines: cyclisation to oxazolones or conversion to acylglycinates when imines are converted to the isomeric enamines prior to deprotection.
• Synthesis of 4-carboethoxy-4-oxazolin-2-ones from 3-nosyloxy-2-ketoesters
  作者：Robert V. Hoffman、M.Catherine Johnson、John F. Okonya

  DOI：10.1016/s0040-4039(97)10854-1

  日期：1998.3

  3-Nosyloxy-2-ketoesters, available from 2-ketoesters, react efficiently with methyl carbamate and tosic acid in refluxing toluene to provide 4-carboalkoxy-4-oxazolin-2-ones in good yields (41-84%). (C) 1998 Elsevier Science Ltd. All rights reserved.