3-(4-甲氧基苯胺基)苯甲酸甲酯 | 579510-29-5

• 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: 3-(4-甲氧基苯胺基)苯甲酸甲酯
• 英文名称: methyl 3-((4-methoxyphenyl)amino)benzoate
• 英文别名: Methyl 3-(4-methoxyanilino)benzoate
• CAS: 579510-29-5
• 化学式: C₁₅H₁₅NO₃
• 分子量: 257.289
• InChiKey: SKQJOMNLPVBZED-UHFFFAOYSA-N

物化性质

• 沸点：
  401.5±30.0 °C(Predicted)
• 密度：
  1.183±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-甲氧基苯胺基)苯甲酸甲酯 在 水 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 以76%的产率得到3-[N-(4-methoxyphenyl)amino]benzoic acid
  参考文献：
  名称：

  Discovery of substituted 3-(phenylamino)benzoic acids as potent and selective inhibitors of type 5 17β-hydroxysteroid dehydrogenase (AKR1C3)

  摘要：

  Aldo-keto reductase 1C3 (AKR1C3) also known as type 5 17 beta-hydroxysteroid dehydrogenase has been implicated as one of the key enzymes driving the elevated intratumoral androgen levels observed in castrate resistant prostate cancer (CRPC). AKR1C3 inhibition therefore presents a rational approach to managing CRPC. Inhibitors should be selective for AKR1C3 over other AKR1C enzymes involved in androgen metabolism. We have synthesized 2-, 3-, and 4-(phenylamino)benzoic acids and identified 3-(phenylamino) benzoic acids that have nanomolar affinity and exhibit over 200-fold selectivity for AKR1C3 versus other AKR1C isoforms. The AKR1C3 inhibitory potency of the 4'-substituted 3-(phenylamino)benzoic acids shows a linear correlation with both electronic effects of substituents and the pK(a) of the carboxylic acid and secondary amine groups, which are interdependent. These compounds may be useful in treatment and/or prevention of CRPC as well as understanding the role of AKR1C3 in endocrinology. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.010
• 作为产物：
  描述：

  4-硝基苯甲醚 在 bis(acetylacetonato)palladium(II) 、 2-(二环己基膦)3,6-二甲氧基-2′,4′,6′-三异丙基-1,1′-联苯 、 苯硅烷 、 四丁基溴化铵 、 caesium carbonate 、 联硼酸频那醇酯 作用下， 以 甲苯 为溶剂， 反应 40.0h， 生成 3-(4-甲氧基苯胺基)苯甲酸甲酯
  参考文献：
  名称：

  硝基芳烃作为亲电子试剂和芳胺替代物在 Buchwald-Hartwig 型 C-N 键构建偶联中的双重作用

  摘要：

  构建 C(sp 2 )–N 键最广泛使用的方法之一是过渡金属催化的芳基卤化物/硼酸与胺的交叉偶联，称为乌尔曼缩合、Buchwald-Hartwig 胺化和 Chan –拉姆联轴器。然而，芳基卤化物/硼酸通常需要多步制备，同时产生大量腐蚀性和有毒废物，使得该反应不太有吸引力。在此，我们提出了一种前所未有的方法，通过Buchwald-Hartwig 型反应形成 C(sp 2 )–N，使用合成上游硝基芳烃作为唯一起始原料，从而消除了对芳基卤化物和预先形成的芳基胺的需要。从硝基芳烃一步获得了多种对称的二芳基胺和三芳基胺，更重要的是，还通过一锅/两步法高选择性地合成了各种不对称的二芳基胺和三芳基胺。此外，放大实验的成功、药物中间体的后期功能化以及空穴传输材料TCTA的快速制备展示了该方案在合成化学中的实用性和实用性。机理研究表明，这种转化可能通过硝基芳烃还原原位生成的芳胺中间体进行，随后与另一种硝基芳烃发生脱硝

  DOI：

  10.1039/d3sc06618e

文献信息

• [EN] NITROSODIPHENYLAMINE DERIVATIVES AND THEIR PHARMACEUTICAL USE AGAINST OXIDATIVE STRESS PATHOLOGIES<br/>[FR] DERIVES DE NITROSODIPHENYLAMINE ET LEUR UTILISATION PHARMACEUTIQUE CONTRE LES PATHOLOGIES LIEES AU STRESS OXYDATIF
  申请人：MERCK PATENT GMBH

  公开号：WO2003076406A1

  公开（公告）日：2003-09-18

  Compounds of formula (I) in which each of the phenyl rings represented is optionally substituted one or more times; n represents an integer selected from 0, 1, 2, 3, 4 and 5; W represents -CO-or -SO2-; Z represents H; alkyl; aryl; or arylalkyl; R1 represents any monovalent organic group; and the pharmaceutically acceptable salts thereof, can be used in the treatment of pathologies that are characterized by an oxidative stress condition.

  式（I）中的化合物，其中所代表的苯环可以选择性地被取代一次或多次；n代表从0、1、2、3、4到5中选择的整数；W代表-CO-或-SO2-；Z代表H；烷基；芳基；或芳基烷基；R1代表任何一价有机基团；以及其药学上可接受的盐，可用于治疗以氧化应激状态为特征的病理情况。
• Light‐Promoted C–N Coupling of Aryl Halides with Nitroarenes
  作者：Gang Li、Liu Yang、Jian‐Jun Liu、Wei Zhang、Rui Cao、Chao Wang、Zunting Zhang、Jianliang Xiao、Dong Xue

  DOI：10.1002/anie.202012877

  日期：2021.3

  A photochemical C–N coupling of aryl halides with nitroarenes is demonstrated for the first time. Catalyzed by a NiII complex in the absence of any external photosensitizer, readily available nitroarenes undergo coupling with a variety of aryl halides, providing a step‐economic extension to the widely used Buchwald–Hartwig C–N coupling reaction. The method tolerates coupling partners with steric‐congestion

  首次证明了芳基卤化物与硝基芳烃的光化学C–N偶联。在没有任何外部光敏剂的情况下，通过Ni II络合物的催化，易得的硝基芳烃与各种芳基卤化物偶合，为广泛使用的Buchwald-Hartwig C-N偶合反应提供了经济上的扩展。该方法耐受具有对碱基和亲核试剂敏感的空间拥塞和官能团的偶联伴侣。机理研究表明，该反应是通过将由Ni I / Ni III循环生成的芳基加至亚硝基芳烃中间体而进行的。
• Nitrosodiphenylamine derivatives and their pharmaceutical use against oxidative stress pathologies
  申请人：Lardy Claude

  公开号：US20050154232A1

  公开（公告）日：2005-07-14

  Compounds of formula (I) in which each of the phenyl rings represented is optionally substituted one or more times; n represents an integer selected from 0, 1, Z, 3, 4 and 5; W represents —CO— or —SO— 2 ; Z represents H; alkyl; aryl; or arylalkyl R 1 represents any monovalent organic group; and the pharmaceutically acceptable salts thereof, can be used in the treatment of pathologies that are characterized by an oxidative stress condition.

  公式（I）的化合物，其中所代表的苯环均可选择性地取代一次或多次；n表示选自0、1、Z、3、4和5的整数；W表示—CO—或—SO—2；Z表示H、烷基、芳基或芳基烷基；R1表示任何一价有机基团；以及其药学上可接受的盐，可用于治疗具有氧化应激状态的病理学。
• Novel compounds
  申请人：Demont Hubert Emmanuel

  公开号：US20060211740A1

  公开（公告）日：2006-09-21

  The present invention relates to novel hydroxyethylamine compounds having Asp2 (β-secretase, BACE1 or Memapsin) inhibitory activity, processes for their preparation, to compositions containing them and to their use in the treatment of diseases characterised by elevated β-amyloid levels or β-amyloid deposits, particularly Alzheimer's disease.

  本发明涉及一种新型的羟乙基胺化合物，具有Asp2（β-分泌酶，BACE1或Memapsin）抑制活性，其制备过程，含有它们的组合物以及它们在治疗β-淀粉样蛋白水平或β-淀粉样蛋白沉积物增高的疾病，尤其是阿尔茨海默病中的应用。
• Transition-metal-catalyzed carbon-nitrogen bond-forming methods using carbene ligands
  申请人：——

  公开号：US20040044250A1

  公开（公告）日：2004-03-04

  The present invention relates to a process for the preparation of N-aryl amine and N-aryl amide compounds. Generally, the process of the present invention involves reacting a compound having a primary or secondary amino or amido group with an arylating compound, in the presence of a weak base and a transition metal catalyst, under reaction conditions effective to form an N-aryl amine or N-aryl amide compound, the transition metal catalyst comprising a Group 8 metal, e.g., Ni, Pd, or Pt, and at least one carbene-containing ligand. Typically, the transition metal catalyst is formed in a preceding step from the conjugate acid form of the carbene ligand, a stoichiometric amount of a strong base, and a Group 8 metal atom or ion.

  本发明涉及一种制备N-芳基胺和N-芳基酰胺化合物的方法。一般来说，本发明的方法涉及在弱碱和过渡金属催化剂的存在下，将具有一级或二级氨基或酰胺基的化合物与芳基化合物反应，形成N-芳基胺或N-芳基酰胺化合物的反应条件有效。过渡金属催化剂包括第8族金属，例如Ni、Pd或Pt，以及至少一个含卡宾的配体。通常，过渡金属催化剂是在前一步中由卡宾配体的共轭酸形式、一定量的强碱和第8族金属原子或离子形成的。