ethyl 4-((4-methoxyphenyl)amino)benzoate | 458550-53-3

• 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: ethyl 4-((4-methoxyphenyl)amino)benzoate
• 英文别名: Ethyl 4-(4-methoxyanilino)benzoate
• CAS: 458550-53-3
• 化学式: C₁₆H₁₇NO₃
• 分子量: 271.316
• InChiKey: VSMMFUXCZNPXMA-UHFFFAOYSA-N

物化性质

• 熔点：
  86-88 °C
• 沸点：
  416.8±30.0 °C(Predicted)
• 密度：
  1.160±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  ethyl 4-((4-methoxyphenyl)amino)benzoate 在 盐酸 、 水 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 potassium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 生成
  参考文献：
  名称：

  Evaluation of NovelN-(piperidine-4-yl)benzamide Derivatives as Potential Cell Cycle Inhibitors in HepG2 Cells

  摘要：

  In this study, a series of novel N‐(piperidine‐4‐yl)benzamide derivatives was designed, synthesized, and evaluated for antitumor activity. Some compounds were found to have potent antitumor activity. In particular, compound 47 showed the most potent biological activity against HepG2 cells, with an IC50 value of 0.25 μm. Western blot analysis demonstrated that compound 47 inhibited the expression of cyclin B1 and p‐Rb and enhanced the expression of p21, p53, Rb, and phospho‐adenosine monophosphate‐activated protein kinase (p‐AMPK). Further, cell cycle arrest was observed by flow cytometry (FCM). In summary, compound 47 was screened to have potential activity for the treatment of hepatocarcinoma via the induction of cell cycle arrest by a p53/p21‐dependent pathway.

  DOI：

  10.1111/cbdd.12484
• 作为产物：
  描述：

  C₁₆H₁₆NO₄^(1-)*Cl^(1-)*Zn⁽²⁺⁾ 在 sodium tetrahydroborate 、 iron(II) chloride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 15.0h， 以219 mg的产率得到ethyl 4-((4-methoxyphenyl)amino)benzoate
  参考文献：
  名称：

  通过向亚硝基芳烃中添加官能化的锌试剂来合成多官能仲胺。

  摘要：

  在乙醇中用FeCl2和NaBH4还原处理后，在乙醇中镁盐和LiCl的存在下，将官能化的芳基，杂芳基或金刚烷基锌试剂添加到各种亚硝基芳烃中，可以高收率得到相应的多官能仲胺。

  DOI：

  10.1039/c4cc08846h

文献信息

• A terphenyl phosphine as a highly efficient ligand for palladium-catalysed amination of aryl halides with 1° anilines
  作者：Fabin Zhou、Lixue Zhang、Ji-cheng Shi

  DOI：10.1016/j.jcat.2021.08.017

  日期：2021.10

  A terphenyl phosphine ligand (2,6-bis(2,4,6-triisopropylphenyl)phenyl-dicyclohexylphosphine, TXPhos) and its supported palladium complex [(TXPhos)(allyl)PdCl] have been developed and the catalyst system is highly efficient in amination of aryl halides with 1° anilines, especially effective for densely functionalized substrates including both partners possessing ortho-ester, acetyl, nitrile and nitro

  已开发出三联苯膦配体（2,6-双（2,4,6-三异丙基苯基）苯基-二环己基膦，TXPhos）及其负载的钯配合物[(TXPhos)(allyl)PdCl]，该催化剂体系在芳基卤化物与 1° 苯胺的胺化，对密集官能化的底物特别有效，包括具有原酸酯、乙酰基、腈和硝基的两个伙伴。使用TXPhos负载的催化剂体系，前所未有地实现了许多合作伙伴的组合，基础范围甚至扩展到了KOAc，这甚至是2-硝基氯苯胺化的最佳选择。
• [EN] NITROSO DERIVATIVES OF DIPHENYLAMINE<br/>[FR] DERIVES NITROSO DE DIPHENYLAMINE
  申请人：MERCK PATENT GMBH

  公开号：WO2005051896A1

  公开（公告）日：2005-06-09

  The invention relates to a compound of the formula (I) in which: - R1 represents, independently of each other, a halogen atom; an aliphatic hydrocarbon-based group optionally substituted and/or optionally interrupted by one or more oxygen or sulfur atoms; a nitro group; a cyano group; an amino group; a mono- or dialkylamino group; an alkylcarbonyl group; a carboxyl group; an alkylcarbonylamino group; an alkylsulfonyl group; - R2 represents, independently of each other, a cyano group; a hydroxyl group, an alkylcarbonyl group; a carboxyl group; an alkoxycarbonyl group; an unsubstituted amide group; or a linear or branched alkyl group substituted by a cyano, hydroxyl, carboxyl, alkoxycarbonyl or unsubstituted amide group; - i and j independently being 1 to 5, with the exclusion of the compound for which i and j = 1 and R1 = carboxyl and R2 = alkoxycarbonyl or R1 = CF3 and R2 = carboxyl, and also the pharmaceutically acceptable derivatives, salts, solvates and stereoisomers thereof, including mixtures thereof in all proportions.

  该发明涉及以下式(I)的化合物：- R1分别表示卤素原子；一种基于脂肪烃的基团，该基团可以选择性地被一个或多个氧或硫原子取代和/或中断；硝基团；氰基团；氨基团；一种单烷基或二烷基氨基团；一种烷基羰基团；羧基团；一种烷基羰基氨基团；一种烷基磺酰基团；- R2分别表示氰基团；羟基团；烷基羰基团；羧基团；烷氧羰基团；未取代酰胺基团；或由氰基、羟基、羧基、烷氧羰基或未取代酰胺基团取代的线性或支链烷基团；- i和j独立地为1到5，不包括当i和j = 1且R1 = 羧基和R2 = 烷氧羰基或R1 = CF3和R2 = 羧基时的化合物，以及其药学上可接受的衍生物、盐、溶剂合物和立体异构体，包括所有比例的混合物。
• [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。
• Aminations of Aryl Bromides in Water at Room Temperature
  作者：Bruce H. Lipshutz、David W. Chung、Brian Rich

  DOI：10.1002/adsc.200900323

  日期：2009.8

  Unsymmetrical di- and triarylamines can be formed under green chemistry conditions, taking advantage of micellar catalysis leading to palladium-catalyzed aminations at ambient temperatures in water as the only medium.

  不对称的二芳基胺和三芳基胺可以在绿色化学条件下形成，利用胶束催化导致钯催化胺化在环境温度下在水中作为唯一介质。
• A New General Preparation of Polyfunctional Diarylamines by the Addition of Functionalized Arylmagnesium Compounds to Nitroarenes
  作者：Ioannis Sapountzis、Paul Knochel

  DOI：10.1021/ja026718r

  日期：2002.8.1

  The addition of functionalized arylmagnesium halides to nitroarenes in THF (-20 degrees C, 2 h) provides, after reductive workup (FeCl(2), NaBH(4)), various polyfunctional diarylamines in 63-86% yield. Heterocyclic arylated amines can be prepared by this one-pot procedure. A mechanistic rationale of this reaction is given.

  在 THF 中向硝基芳烃添加官能化芳基镁卤化物（-20 摄氏度，2 小时），在还原处理后（FeCl(2)、NaBH(4))，各种多功能二芳基胺的产率为 63-86%。杂环芳基化胺可以通过这种一锅法制备。给出了该反应的机械原理。