5-phenyl-4-ethoxycarbonyl-4-oxazolin-2-one | 4113-70-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-phenyl-4-ethoxycarbonyl-4-oxazolin-2-one
• 英文别名: ethyl 2-oxo-5-phenyl-2,3-dihydrooxazole-4-carboxylate；2-oxo-5-phenyl-2,3-dihydro-oxazole-4-carboxylic acid ethyl ester；ethyl 2-oxo-5-phenyl-3H-1,3-oxazole-4-carboxylate
• CAS: 4113-70-6
• 化学式: C₁₂H₁₁NO₄
• 分子量: 233.224
• InChiKey: KRAOAMRHIGTIQQ-UHFFFAOYSA-N

物化性质

• 熔点：
  171-172 °C
• 密度：
  1.296±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  5-phenyl-4-ethoxycarbonyl-4-oxazolin-2-one 在 sodium hydroxide 作用下， 生成 2-oxo-5-phenyl-2,3-dihydro-oxazole-4-carboxylic acid
  参考文献：
  名称：

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

  摘要：

  DOI：
• 作为产物：
  描述：

  3-苯基-2-氧代丙酸乙酯 在 silver trifluoromethanesulfonate 、 copper(ll) bromide 作用下， 以 氯仿 、 乙酸乙酯 、 甲苯 为溶剂， 反应 18.0h， 生成 5-phenyl-4-ethoxycarbonyl-4-oxazolin-2-one
  参考文献：
  名称：

  Synthesis of 2-Oxazolone-4-carboxylates from 3-Nosyloxy- and 3-Bromo-2-ketoesters

  摘要：

  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.

  DOI：

  10.1021/jo010630z

文献信息

• Convergent Synthesis of 2-Oxazolone-4-carboxylates Esters by Reaction of Aldehydes with Ambivalent <i>N</i>-Cbz-α-Tosylglycinate Ester
  作者：Masahiro Abe、Baptiste Picard、Michaël De Paolis

  DOI：10.1021/acs.orglett.0c01703

  日期：2020.6.19

  N-Cbz-α-tosylglycinate ester was combined with aldehydes in a redox-neutral sequence leading to 2-oxazolone-4-carboxylates with high functional group tolerance. While the scope of the method was delineated to primary and secondary aliphatic aldehydes as well as aromatics, no racemization occurred with chiral aldehydes such as Garner’s. Hitherto unknown, this process relies on the ambivalent role of

  N -Cbz-α-甲苯磺酰基甘氨酸酯与醛以氧化还原中性顺序结合，产生具有高官能团耐受性的2-恶唑酮-4-羧酸酯。尽管该方法的范围被限定为伯和仲脂族醛以及芳族化合物，但手性醛（如Garner's）未发生外消旋作用。迄今为止未知，该过程依赖于N -Cbz-α-甲苯磺酰基甘氨酸酯作为亲核试剂的矛盾作用。
• 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.
• 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.