5-methyl-4-ethoxycarbonyl-4-oxazolin-2-one | 197719-33-8

• 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-methyl-4-ethoxycarbonyl-4-oxazolin-2-one
• 英文别名: Ethyl 5-methyl-2-oxo-2,3-dihydrooxazole-4-carboxylate；ethyl 5-methyl-2-oxo-3H-1,3-oxazole-4-carboxylate
• CAS: 197719-33-8
• 化学式: C₇H₉NO₄
• 分子量: 171.153
• InChiKey: YVJUSFMTOGLAID-UHFFFAOYSA-N

物化性质

• 密度：
  1.261±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 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-methyl-4-ethoxycarbonyl-4-oxazolin-2-one 在 palladium on activated charcoal 氢气 作用下， 反应 1.0h， 生成 (4S,5S)-3-Acetyl-5-methyl-2-oxo-oxazolidine-4-carboxylic acid ethyl 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：

  potassium cyanate 、 2-氯乙酰乙酸乙酯 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以51%的产率得到5-methyl-4-ethoxycarbonyl-4-oxazolin-2-one
  参考文献：
  名称：

  对映体合成L-苏氨酸

  摘要：

  L-苏氨酸的对映体选择性合成

  DOI：

  10.1002/hlca.19870700128

文献信息

• Chemistry of 5-oxodihydroisoxazoles. Part 18.1 Synthesis of oxazoles by the photolysis and pyrolysis of 2-acyl-5-oxo-2,5-dihydroisoxazoles
  作者：Rolf H. Prager、Jason A. Smith、Ben Weber、Craig M. Williams

  DOI：10.1039/a700134g

  日期：——

  N-Acylisoxazol-5-ones lose carbon dioxide under photochemical and thermal conditions affording iminocarbenes which undergo intramolecular cyclisation through the oxygen of the acyl group to give oxazoles. Under photochemical conditions those acylisoxazolones with electron withdrawing groups at C-4 usually give high yields of oxazoles, while those with electron donating groups at C-4 give only poor yields: the reverse is observed under thermal conditions.

  N-酰基异恶唑-5-酮在光化学和热条件下失去二氧化碳，生成亚胺卡宾，随后通过酰基团的氧进行分子内环化，形成恶唑。在光化学条件下，C-4位带有吸电子基团的酰基异恶唑酮通常产生高产率的恶唑，而在C-4位带有供电子基团的酰基异恶唑酮仅产生低产率：在热条件下观察到相反的结果。
• 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.