Ethyl 2-<<(p-nitrophenyl)sulfonyl>oxy>-2-benzoylacetate | 124716-83-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Ethyl 2-<<(p-nitrophenyl)sulfonyl>oxy>-2-benzoylacetate
• 英文别名: Ethyl 2-(4-nitrophenyl)sulfonyloxy-3-oxo-3-phenylpropanoate
• CAS: 124716-83-2
• 化学式: C₁₇H₁₅NO₈S
• 分子量: 393.374
• InChiKey: CXFKBFCSXVEQIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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>-2-benzoylacetate 在 sodium tetrahydroborate 、 三乙胺 作用下， 以 乙醇 、 乙腈 为溶剂， 生成 反式-3-苯基环氧丙酸乙酯
  参考文献：
  名称：

  Synthesis and reactions of 3-hydroxy-2-nosyloxy esters produced by the stereoselective reduction of 2-nosyloxy-3-keto esters

  摘要：

  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.

  DOI：

  10.1021/jo00024a013
• 作为产物：
  描述：

  4-nitrobenzenesulfonyl peroxide 、 苯甲酰乙酸乙酯 以 二氯甲烷 为溶剂， 以65%的产率得到Ethyl 2-<<(p-nitrophenyl)sulfonyl>oxy>-2-benzoylacetate
  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

• Synthetic transformations using arenesulfonyloxy groups, first as electrophiles, then as leaving groups
  作者：Robert V. Hoffman

  DOI：10.1016/s0040-4020(01)86369-9

  日期：1991.1
• Lee, Jong Chan; Choi, Ju-Hee, Synlett, 2001, # 2, p. 234 - 235
  作者：Lee, Jong Chan、Choi, Ju-Hee

  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.
• 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
• 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：——