2-nitrophenoxyacetanilide | 20916-31-8

• 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: 2-nitrophenoxyacetanilide
• 英文别名: (2-nitro-phenoxy)-acetic acid anilide；(2-Nitro-phenoxy)-essigsaeure-anilid；N-Phenyl-o-nitrophenoxyessigsaeureamid；o-Nitro-phenoxyessigsaeure-anilid；2-(2-nitrophenoxy)-N-phenylacetamide
• CAS: 20916-31-8
• 化学式: C₁₄H₁₂N₂O₄
• 分子量: 272.26
• InChiKey: RWOMDKRAEGBSSH-UHFFFAOYSA-N

物化性质

• 熔点：
  121-122 °C(Solv: ethanol (64-17-5))
• 沸点：
  533.7±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)：
  2.3
• 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：

  2-nitrophenoxyacetanilide 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 2-硝基二苯胺
  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
• 作为产物：
  描述：

  2-硝基苯氧乙酸 在 氯化亚砜 作用下， 生成 2-nitrophenoxyacetanilide
  参考文献：
  名称：

  Minton; Stephen, Journal of the Chemical Society, 1922, vol. 121, p. 1603

  摘要：

  DOI：

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。
• Intramolecular aminolysis of amides. Effects of electronic variation in the attacking and leaving groups
  作者：Kenneth L. Kirk、Louis A. Cohen

  DOI：10.1021/ja00778a033

  日期：1972.11
• 2-Nitrophenoxyacetanilide: a chain of rings generated by C—H...O hydrogen bonds
  作者：Christopher Glidewell、John N. Low、Janet M. S. Skakle、James L. Wardell

  DOI：10.1107/s010827010400513x

  日期：2004.4.15

  In molecules of the title compound, C14H12N2O4, the conformation is dominated by an intramolecular N-H...O hydrogen bond in which one of the nitro O atoms is the acceptor. The molecules are linked by paired C-H...O hydrogen bonds [H...O = 2.41 Angstrom, C...O = 3.2990 (17) Angstrom and C-H...O = 156degrees] into centrosymmetric R-2(2)(14) dimers; these dimers are linked weakly into chains of alternating R-2(2)(14) and R-4(4)(40) rings by a second C-H...O hydrogen bond [H...O = 2.55 Angstrom, C...O = 3.5006 (15) Angstrom and C-H...O = 162degrees].