N-(4-nitrophenyl)-3-(trifluoromethyl)aniline | 369-90-4

• 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: N-(4-nitrophenyl)-3-(trifluoromethyl)aniline
• 英文别名: 4-Nitro-3'-trifluoromethyldiphenylamine；(4-nitro-phenyl)-(3-trifluoromethyl-phenyl)-amine；(4-Nitro-phenyl)-(3-trifluormethyl-phenyl)-amin；4-Nitro-3'-trifluormethyl-diphenylamin；4-Nitro-3'-trifluoromethyldiphenylamin；N-(4-Nitrophenyl)-3-(trifluoromethyl)benzenamine
• CAS: 369-90-4
• 化学式: C₁₃H₉F₃N₂O₂
• 分子量: 282.222
• InChiKey: UDHNPQBBLGONPJ-UHFFFAOYSA-N

物化性质

• 熔点：
  145 °C
• 沸点：
  370.5±42.0 °C(Predicted)
• 密度：
  1.405±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(4-nitrophenyl)-3-(trifluoromethyl)aniline 在 palladium 10% on activated carbon 、 甲酸铵 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 20.0h， 生成 1-(4-{[3-(trifluoromethyl)phenyl]amino}phenyl)urea
  参考文献：
  名称：

  Optimization of diaryl amine derivatives as kinesin spindle protein inhibitors

  摘要：

  Structure-activity relationship studies of diaryl amine-type KSP inhibitors were carried out. Diaryl amine derivatives with a pyridine ring or urea group were less active when compared with the parent carboline and carbazole derivatives. Optimization studies of a lactam-fused diphenylamine-type KSP inhibitor revealed that the aniline NH group and 3-CF3 phenyl group were indispensable for potent KSP inhibition. Modification with a seven-membered lactam-fused phenyl group and a 4-(trifluoromethyl)pyridin-2-yl group improved aqueous solubility while maintaining potent KSP inhibitory activity. From these studies, we identified novel diaryl amine-type KSP inhibitors with a favorable balance of potency and solubility. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.04.008
• 作为产物：
  描述：

  间溴三氟甲苯 、 4-硝基苯胺 在 tris-(dibenzylideneacetone)dipalladium(0) 、 sodium t-butanolate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 甲苯 为溶剂， 反应 9.0h， 以70%的产率得到N-(4-nitrophenyl)-3-(trifluoromethyl)aniline
  参考文献：
  名称：

  Optimization of diaryl amine derivatives as kinesin spindle protein inhibitors

  摘要：

  Structure-activity relationship studies of diaryl amine-type KSP inhibitors were carried out. Diaryl amine derivatives with a pyridine ring or urea group were less active when compared with the parent carboline and carbazole derivatives. Optimization studies of a lactam-fused diphenylamine-type KSP inhibitor revealed that the aniline NH group and 3-CF3 phenyl group were indispensable for potent KSP inhibition. Modification with a seven-membered lactam-fused phenyl group and a 4-(trifluoromethyl)pyridin-2-yl group improved aqueous solubility while maintaining potent KSP inhibitory activity. From these studies, we identified novel diaryl amine-type KSP inhibitors with a favorable balance of potency and solubility. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.04.008

文献信息

• Ligand-Enabled Gold-Catalyzed C(sp²)–N Cross-Coupling Reactions of Aryl Iodides with Amines
  作者：Manjur O. Akram、Avishek Das、Indradweep Chakrabarty、Nitin T. Patil

  DOI：10.1021/acs.orglett.9b03082

  日期：2019.10.4

  example of ancillary (P,N)-ligand-enabled gold-catalyzed C-N cross-coupling reactions of aryl iodides with amines is reported. The high generality of the reaction in de novo synthesis, late-stage modifications, and cascade processes to access functionalized indolinones and carbazoles underscores the synthetic potential of the presented strategy. Monitoring the reaction with ESI-HRMS and NMR provided strong

  报道了芳基碘化物与胺的辅助（P，N）-配体使能的金催化的CN交叉偶联反应的第一个例子。在从头合成，后期修饰和级联过程中获得官能化的吲哚酮和咔唑的反应具有很高的通用性，这突出了所提出策略的合成潜力。用ESI-HRMS和NMR监测反应为原位形成假定的高价Au（III）中间体提供了有力的证据。
• [EN] 1, 8-NAPHTHYRIDINE DERIVATIVES AS ANTIDIABETICS<br/>[FR] DERIVES 1, 8-NAPHTYRIDINE UTILISES COMME ANTIDIABETIQUES
  申请人：BAYER AG

  公开号：WO2003027112A1

  公开（公告）日：2003-04-03

  The invention relates generally to naphthyridine derivatives of the formula wherein one of U, X, Y and Z is nitrogen and the others are C-R, where R is hydrogen or a substituent. More specifically, the invention relates to 1,8-naphthyridine derivatives and pharmaceutical compositions containing such derivatives. Methods of the invention comprise administration of a naphthyridine derivative of the invention for the treatment of diabetes and related disorders.

  本发明涉及公式的萘啶衍生物，其中U、X、Y和Z中的一个是氮，其余为C-R，其中R是氢或取代基。更具体地，本发明涉及1,8-萘啶衍生物和含有这种衍生物的药物组合物。本发明的方法包括给予本发明的萘啶衍生物治疗糖尿病及相关疾病。
• 10.1039/d4cc01935k
  作者：Liu, Zi、Greaney, Michael F.

  DOI：10.1039/d4cc01935k

  日期：——

  Intermolecular aminoarylation of alkynes is described, via addition of diarylanilines to alkynes and Smiles–Truce rearrangement. The transformation manipulates the C–N bond of anilines directly, with no requirement for organometallic reagents or transition metal catalysis. The enaminoate products are versatile building blocks for different classes of heterocycles.

  描述了通过向炔烃中添加二芳基苯胺和 Smiles-Truce 重排来进行炔烃的分子间氨基芳基化。该转化直接操纵苯胺的C-N键，不需要有机金属试剂或过渡金属催化。烯胺酸酯产品是不同类别杂环的通用构建单元。
• Tschernezkii et al., Zhurnal Obshchei Khimii, 1955, vol. 25, p. 2161,2167; engl. Ausg. S. 2123, 2128
  作者：Tschernezkii et al.

  DOI：——

  日期：——
• Viswanathan, N.; Desai, Ranjit C., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1981, vol. <B> 20, # 4, p. 308 - 310
  作者：Viswanathan, N.、Desai, Ranjit C.

  DOI：——

  日期：——