2-Chloro-N-(2,4-dichloro-phenyl)-N-phenyl-acetamide | 626239-02-9

• 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-Chloro-N-(2,4-dichloro-phenyl)-N-phenyl-acetamide
• 英文别名: 2-chloro-N-(2,4-dichlorophenyl)-N-phenylacetamide
• CAS: 626239-02-9
• 化学式: C₁₄H₁₀Cl₃NO
• 分子量: 314.599
• InChiKey: LWQBRCQDVNDCPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-Chloro-N-(2,4-dichloro-phenyl)-N-phenyl-acetamide 在 sodium hydride 、 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 44.0h， 生成 N-(2,4-二氯苯基)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：

  N-(2,4-二氯苯基)苯胺 、 氯乙酰氯 反应 6.0h， 以93%的产率得到2-Chloro-N-(2,4-dichloro-phenyl)-N-phenyl-acetamide
  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

• Synthesis and quantitative structure-activity relationships of diclofenac analogs
  作者：Peter Moser、Alfred Sallmann、Irmgard Wiesenberg

  DOI：10.1021/jm00171a008

  日期：1990.9

  The synthesis of a series of 2-anilinophenylacetic acids, close analogues of diclofenac, is described. These compounds were tested in two models used for evaluating the activity of nonsteroidal antiinflammatory drugs (NSAID's), inhibition of cyclooxygenase enzyme activity in vitro, and adjuvant-induced arthritis (AdA) in rats. Statistically significant correlations were found between the inhibitory activities of the compounds in these two models, indicating that cyclooxygenase inhibition seems to be the underlying mechanism for the antiinflammatory activity of these compounds. Quantitative structure-activity relationship (QSAR) analysis revealed that the crucial parameters for activity in both models were the lipophilicity and the angle of twist between the two phenyl rings. Optimal activities were associated with halogen or alkyl substituents in both ortho positions of the anilino ring. Compounds with OH groups in addition to two ortho substituents or compounds with only one or no ortho substituents were less active.
• A Convenient Preparation of <i>N</i>-Alkyl and <i>N</i>-Arylamines by Smiles Rearrangement—Synthesis of Analogues of Diclofenac
  作者：M. S. Wadia、D. V. Patil

  DOI：10.1081/scc-120021996

  日期：2003.1.8

  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.