Ethyl 2-<<(p-nitrophenyl)sulfonyl>oxy>acetoacetate | 124716-79-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Ethyl 2-<<(p-nitrophenyl)sulfonyl>oxy>acetoacetate
• 英文别名: ethyl 2-(((p-nitrophenyl)sulfonyl)oxy)acetoacetate；Ethyl 2-(4-nitrophenyl)sulfonyloxy-3-oxobutanoate
• CAS: 124716-79-6
• 化学式: C₁₂H₁₃NO₈S
• 分子量: 331.303
• InChiKey: HNNMRSVKQJUEAJ-UHFFFAOYSA-N

物化性质

• 熔点：
  84-86 °C(Solv: ethyl acetate (141-78-6); ethyl ether (60-29-7))
• 沸点：
  482.3±45.0 °C(Predicted)
• 密度：
  1.422±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  141
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Ethyl 2-<<(p-nitrophenyl)sulfonyl>oxy>acetoacetate 在 三乙胺 作用下， 以 乙醇 为溶剂， 生成 2,3-二氧代丁酸乙酯
  参考文献：
  名称：

  咪唑与1,2,4-三嗪的分子内电子逆需求Diels-Alder反应：通往1,2,3,4-四氢-1,5-萘啶和相关杂环的新途径

  摘要：

  咪唑和1,2,4-三嗪之间的分子内逆电子需求的Diels-Alder反应由三亚甲基系链从咪唑N1位置连接到三嗪C3，从而以极好的收率进行生产1,2,3,4-四氢-1，5-萘啶。该反应通过环加成反应进行，随后损失氮气，然后逐步损失腈。使用四亚甲基系链的类似分子内环加成反应也以可接受的收率得到了2,3,4,5-四氢-1 H-吡啶并[3,2- b ]氮杂。微波辐射也可以促进产生四氢-1，5-萘啶的反应。

  DOI：

  10.1021/jo040193z
• 作为产物：
  描述：

  4-nitrobenzenesulfonyl peroxide 、 乙酰乙酸乙酯 以 二氯甲烷 为溶剂， 以57%的产率得到Ethyl 2-<<(p-nitrophenyl)sulfonyl>oxy>acetoacetate
  参考文献：
  名称：

  Synthesis of 2-[[(p-nitrophenyl)sulfonyl]oxy] 3-keto esters from 3-keto esters and (p-nitrophenyl)sulfonyl peroxide

  摘要：

  DOI：

  10.1021/jo00291a030

文献信息

• 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.
• 2-[[(p-Nitrophenyl)sulfonyl]oxy]-3-keto esters: versatile intermediates for the preparation of 1,2,3-tricarbonyl compounds
  作者：Robert V. Hoffman、Hwa Ok Kim、Anna Lee Wilson

  DOI：10.1021/jo00296a047

  日期：1990.4
• Synthesis and reactions of 3-hydroxy-2-nosyloxy esters produced by the stereoselective reduction of 2-nosyloxy-3-keto esters
  作者：Robert V. Hoffman、Hwa Ok Kim

  DOI：10.1021/jo00024a013

  日期：1991.11

  The reduction of 2-nosyloxy-3-keto esters is an effective method for the preparation of 3-hydroxy-2-nosyloxy esters. The reduction is stereoselective for the syn isomer. The anti isomer can be produced as the major product by the addition of p-nitrobenzenesulfonyl peroxide to ketene bis-silyl acetal derivatives of 3-hydroxy esters. The diastereomers are separable chromatographically and can be converted stereospecifically to glycidic esters and 2-azido-3-hydroxy esters. As such they appear to have excellent potential as versatile synthetic intermediates for the synthesis of 1,2,3-trifunctional substances.
• HOFFMAN, ROBERT V.;WILSON, ANNA LEE;KIM, HWA-OK, J. ORG. CHEM., 55,(1990) N, C. 1267-1270
  作者：HOFFMAN, ROBERT V.、WILSON, ANNA LEE、KIM, HWA-OK

  DOI：——

  日期：——