ω-Benzoylamido-p-nitro-acetophenon | 1846-31-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ω-Benzoylamido-p-nitro-acetophenon
• 英文别名: N-(4-nitro-phenacyl)-benzamide；N-(4-Nitro-phenacyl)-benzamid；N-[2-(4-nitrophenyl)-2-oxoethyl]benzamide
• CAS: 1846-31-7
• 化学式: C₁₅H₁₂N₂O₄
• 分子量: 284.271
• InChiKey: JRCUDXOHBLPYBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  92
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ω-Benzoylamido-p-nitro-acetophenon 在 4-二甲氨基吡啶 、 水 、 碘 作用下， 以 1,4-二氧六环 为溶剂， 以25 %的产率得到N-(2-(4-nitrophenyl)-2-oxoacetyl)benzamide
  参考文献：
  名称：

  DMAP 通过水/醇的氧气输送促进 α-氨基酮的氧化官能化

  摘要：

  本文展示了 α-氨基酮的新型氧化官能化，产生相应的 α-酮酰胺和 α-酰亚胺酯。该反应通过水/醇的氧气输送以及电子受体和 4-二甲基氨基吡啶 (DMAP) 进行。机理研究表明DMAP具有亲核催化和质子夺取的双重功能。

  DOI：

  10.1039/d4cc02348j
• 作为产物：
  描述：

  4-硝基苯乙烯 在 盐酸 、 sodium azide 、 一氯化碘 作用下， 以 二氯甲烷 、 氘代甲醇-d 、 水 、 乙腈 为溶剂， 反应 6.0h， 生成 ω-Benzoylamido-p-nitro-acetophenon
  参考文献：
  名称：

  Rapid and Bifunctional Chemoselective Metabolome Analysis of Liver Disease Plasma Using the Reagent 4‐Nitrophenyl‐2H‐azirine

  摘要：

  Primary sclerosing cholangitis (PSC) is a chronic inflammatory disease of the bile ducts that has been associated with diverse metabolic carboxylic acids. Mass spectrometric techniques are the method of choice for their analysis. However, the broad investigation of this metabolite class remains challenging. Derivatization of carboxylic acids represents a strategy to overcome these limitations but available methods suffer from diverse analytical challenges. Herein, we have designed a novel strategy introducing 4‐nitrophenyl‐2H‐azirine as a new chemoselective moiety for the first time for carboxylic acid metabolites. This moiety was selected as it rapidly forms a stable amide bond and also generates a new ketone, which can be analyzed by our recently developed quant‐SCHEMA method specific for carbonyl metabolites. Optimization of this new method revealed a high reproducibility and robustness, which was utilized to validate 102 metabolic carboxylic acids using authentic synthetic standard conjugates in human plasma samples including nine metabolites that were newly detected. Using this sequential analysis of the carbonyl‐ and carboxylic acid‐metabolomes revealed alterations of the ketogenesis pathway, which demonstrates the vast benefit of our unique methodology. We anticipate that the developed azirine moiety with rapid functional group transformation will find broad application in diverse chemical biology research fields.

  DOI：

  10.1002/anie.202318579

文献信息

• alpha-acylamido-beta-hydroxy nitro substituted propiophenones
  申请人：PARKE DAVIS & CO

  公开号：US02515239A1

  公开（公告）日：1950-07-18
• Tricerri et al., Gazzetta Chimica Italiana, 1954, vol. 84, p. 701,704
  作者：Tricerri et al.

  DOI：——

  日期：——
• Tatsuoka et al., Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1951, vol. 71, p. 604,606
  作者：Tatsuoka et al.

  DOI：——

  日期：——
• Combinatorial discovery of novel fluorescent dyes based on Dapoxyl™
  作者：Qing Zhu、Hai-Shin Yoon、Puja B. Parikh、Young-Tae Chang、Shao Q. Yao

  DOI：10.1016/s0040-4039(02)00999-1

  日期：2002.7

  We have developed a combinatorial method for the fast and effective synthesis of a library based on a known fluorescent dye, Dapoxyl(TM) using parallel solution-phase chemistry. By screening the 140 new compounds using fluorescence-based assays, we identified three new fluorescent dyes with novel properties. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Scoffone; Iliceto, Gazzetta Chimica Italiana, 1951, vol. 81, p. 881,886
  作者：Scoffone、Iliceto

  DOI：——

  日期：——