5-pentyl-4-ethoxycarbonyl-4-oxazolin-2-one

• 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-pentyl-4-ethoxycarbonyl-4-oxazolin-2-one
• 英文别名: ethyl 2-oxo-5-pentyl-3H-1,3-oxazole-4-carboxylate
• 化学式: C₁₁H₁₇NO₄
• 分子量: 227.26
• InChiKey: UIRYSTQZSVBBHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  氨基甲酸甲酯 、 ethyl 3-[(p-nitrobenzenesulfonyl)oxy]-2-oxooctanoate 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 以84%的产率得到5-pentyl-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

• 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.
• 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.