乙酰胺,2-(4-硝基苯氧基)-N-苯基- | 17716-80-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 乙酰胺,2-(4-硝基苯氧基)-N-苯基-
• 英文名称: 2-(4-nitrophenoxy)-N-phenylacetamide
• 英文别名: (4-nitro-phenoxy)-acetic acid anilide；(4-Nitro-phenoxy)-essigsaeure-anilid；p-Nitro-phenoxy-acetanilid (p-Nitro-phenoxyessigsaeure-N-phenyl-anilin)；p-Nitro-phenoxyessigsaeure-anilid；2-(4-Nitrophenoxy)-acetanilid；p-Nitro-phenoxy-acetanilid
• CAS: 17716-80-2
• 化学式: C₁₄H₁₂N₂O₄
• 分子量: 272.26
• InChiKey: LEHIVXDDSQHROR-UHFFFAOYSA-N

物化性质

• 熔点：
  172 °C
• 沸点：
  543.1±30.0 °C(Predicted)
• 密度：
  1.342±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 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：
  84.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙酰胺,2-(4-硝基苯氧基)-N-苯基- 在 盐酸 、 tin 、 丙酮 作用下， 生成 2-(4-aminophenoxy)-N-phenylacetamide
  参考文献：
  名称：

  Kym, Journal fur praktische Chemie (Leipzig 1954), 1897, vol. <2> 55, p. 122

  摘要：

  DOI：
• 作为产物：
  描述：

  4-硝基苯氧乙酸 在 氯化亚砜 作用下， 以 苯 为溶剂， 生成 乙酰胺,2-(4-硝基苯氧基)-N-苯基-
  参考文献：
  名称：

  A Convenient Preparation of N-Alkyl and N-Arylamines by Smiles Rearrangement—Synthesis of Analogues of Diclofenac

  摘要：

  Smiles rearrangement of substituted aryloxyacetamides in which oxygen and-nitrogen are separated by COCH2 group has been successful even when the aryloxy ring carries weak or no electron withdrawing group. Earlier reports of such reactions involved either strong electron withdrawing groups or a special catalyst. The diphenylamines thus obtained gave analogues of diclofenac in only one case.

  DOI：

  10.1081/scc-120021996

文献信息

• Copper-catalyzed transformation of alkyl nitriles to <i>N</i>-arylacetamide using diaryliodonium salts
  作者：Romain Sallio、Pierre-Adrien Payard、Paweł Pakulski、Iryna Diachenko、Indira Fabre、Sabine Berteina-Raboin、Cyril Colas、Ilaria Ciofini、Laurence Grimaud、Isabelle Gillaizeau

  DOI：10.1039/d1ra02305e

  日期：——

  This work reports a simple and efficient method for the copper-catalyzed redox-neutral transformation of alkyl nitriles using eco-friendly diaryliodonium salts and leading to N-arylacetamides. The method features high efficiency, broad substrate scope and good functional group tolerance.

  这项工作报告了一种简单有效的方法，用于使用环保的二芳基碘鎓盐对烷基腈进行铜催化的氧化还原中性转化并生成N-芳基乙酰胺。该方法效率高、底物范围广、官能团耐受性好。
• Parkhe, Anil B.; Bhai, Aziz; Porwal, K. K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1981, vol. 20, # 1, p. 79 - 80
  作者：Parkhe, Anil B.、Bhai, Aziz、Porwal, K. K.、Boparai, K. S.

  DOI：——

  日期：——
• N6-[(Hetero)aryl/(cyclo)alkyl-carbamoyl-methoxy-phenyl]-(2-chloro)-5′-N-ethylcarboxamido-adenosines: The first example of adenosine-related structures with potent agonist activity at the human A2B adenosine receptor
  作者：Pier Giovanni Baraldi、Delia Preti、Mojgan Aghazadeh Tabrizi、Francesca Fruttarolo、Giulia Saponaro、Stefania Baraldi、Romeo Romagnoli、Allan R. Moorman、Stefania Gessi、Katia Varani、Pier Andrea Borea

  DOI：10.1016/j.bmc.2007.01.055

  日期：2007.4

  A new series of N-6-[(hetero)aryl/(cyclo)alkyl-carbamoyl-methoxy-phenyl]-(2-chloro)-5'-N-ethylcarboxamido-adenosines (24-43) has been synthesised and tested in binding assays at hA(1), hA(2A) and hA(3) adenosine receptors, and in a functional assay at the hA(2B) subtype. The examined compounds displayed high potency in activating A(2B) receptors with good selectivity versus A(2A) subtypes. The introduction of an unsubstituted 4-[(phenylcarbamoyl)-methoxyl-phenyI chain at the N-6 position of 5'-N-ethylcarboxamido -adenosine led us to the recognition of compound 24 as a full agonist displaying the highest efficacy of the series (EC50 hA(2B) = 7.3 nM). These compounds represent the first report about adenosine-related structures capable of activating hA2B subtype in the low nanomolar range. (c) 2007 Elsevier Ltd. All rights reserved.
• 391. A rearrangement of o-carbamyl derivatives of diphenyl ether
  作者：Bernard T. Tozer、Samuel Smiles

  DOI：10.1039/jr9380002052

  日期：——
• Irreversible enzyme inhibitors. 197. Water-soluble reversible inhibitors of dihydrofolate reductase with potent antitumor activity derived from 4,6-diamino-1,2-dihydro-2,2-dimethyl-1-phenyl-s-triazine
  作者：B. R. Baker、Wallace T. Ashton

  DOI：10.1021/jm00261a009

  日期：1973.3