N-(2,4-二氯苯基)苯胺 | 58373-59-4

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 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: N-(2,4-二氯苯基)苯胺
• 英文名称: 2,4-dichloro-N-phenylaniline
• 英文别名: (2,4-dichloro-phenyl)-phenyl-amine；(2,4-Dichlor-phenyl)-phenyl-amin；N-Phenyl-2.4-dichlor-anilin；2.4-Dichlor-diphenylamin；2,4-dichloro-N-phenyl-benzenamine；Dichloro-2,4-diphenylamin
• CAS: 58373-59-4
• 化学式: C₁₂H₉Cl₂N
• 分子量: 238.116
• InChiKey: WRQKGHMNRXSQFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(2,4-二氯苯基)苯胺 在 sodium hydride 、 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 74.0h， 生成
  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：

  2,4-Dichlorophenoxyacetanilide 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以52%的产率得到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

文献信息

• Peptide Nanofiber Templated Zinc Oxide Nanostructures as Non-precious Metal Catalyzed N-Arylation of Amines, One-Pot Synthesis of ImidazoHeterocycles and Fused Quinazolines
  作者：Zahra Taherinia、Arash Ghorbani-Choghamarani、Maryam Hajjami

  DOI：10.1007/s10562-018-2580-4

  日期：2019.1

  the method was investigated by N-arylation using reaction of amines with hydroxybenzotriazole as a novel phenylating reagent, one-pot synthesis of imidazoheterocycles by a three-component reaction of 2-aminopyridine, aldehyde, terminal alkyne and preparation of tetracyclic quinazolinone ring by one-pot reaction of isatoic anhydride, amine, and ninhydrin. High yields, low cost of catalyst, environmental

  在本研究中，肽纳米纤维用于固定氧化锌。该纳米颗粒是通过在水溶液中自组装制备的。通过FT-IR、EDS、SEM、TEM、XRD、ICP-OES（电感耦合等离子体发射光谱法）和紫外-可见光（UV-Vis）等一系列技术对制备的催化剂的结构性质进行了检测。光谱学。TEM 图像显示了用氧化锌装饰的肽纳米纤维的项链模型。该方法的通用性通过使用胺与羟基苯并三唑的反应作为新型苯化试剂的N-芳基化，通过2-氨基吡啶、醛、末端炔的三组分反应一锅合成咪唑杂环和制备四环喹唑啉酮环来研究该方法的通用性通过靛红酸酐、胺和茚三酮的一锅反应。
• Triphenyltin chloride as a new source of phenyl group for C-heteroatom and C–C bond formation
  作者：Nasser Iranpoor、Habib Firouzabadi、Elham Etemadi Davan、Abed Rostami、Arash Nematollahi

  DOI：10.1016/j.jorganchem.2013.04.053

  日期：2013.9

  Ph3SnCl is introduced as a very suitable source of phenyl group for coupling with phenols, amines, and thiols in the presence of Cu(OAc)(2) in Et3N at room temperature to give aryl ethers, amines, and arylthio ethers in high yields. In addition, the application of Ph3SnCl in the Stille coupling of aryl halides in the presence of Pd(0) catalyst in PEG 400 at 110 degrees C is discussed. (C) 2013 Published by Elsevier B. V.
• Rioux-Lacoste,C.; Viel,C., Bulletin de la Societe Chimique de France, 1974, p. 2463 - 2470
  作者：Rioux-Lacoste,C.、Viel,C.

  DOI：——

  日期：——
• 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.
• Practical copper-catalyzed N-arylation of amines with 20% aqueous solution of n-Bu4NOH
  作者：Hamidreza Molaei、Mohammad Mehdi Ghanbari

  DOI：10.1016/j.cclet.2011.12.015

  日期：2012.3

  N-Arylation of a wide variety of amines with phenylboronic acid catalyzed by copper acetate under 20% aqueous solution of n-Bu4NOH was accomplished in good to excellent yields (up to 92%) and substrate conversions (up to 96%). (C) 2011 Mohammad Mehdi Ghanbari. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.