N-(3-氯苯基)-4-甲氧基苯酰胺 | 7465-93-2

• 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-(3-氯苯基)-4-甲氧基苯酰胺
• 中文别名: N-(3-氯苯基)-4-甲氧基苯甲酰胺
• 英文名称: N-(p-methoxybenzoyl)-m-chloroaniline
• 英文别名: N-(3-chlorophenyl)-4-methoxybenzamide；4-Methoxy-benzoesaeure-<3-chlor-anilid>；3-chloro-1-(p-methoxybenzoylamino)benzene
• CAS: 7465-93-2
• 化学式: C₁₄H₁₂ClNO₂
• 分子量: 261.708
• InChiKey: SPKOXUOZUKBVLV-UHFFFAOYSA-N

物化性质

• 熔点：
  136 °C
• 沸点：
  327.4±27.0 °C(Predicted)
• 密度：
  1.281±0.06 g/cm3(Predicted)
• 保留指数：
  2443

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 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：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  N-(3-氯苯基)-4-甲氧基苯酰胺 在 劳森试剂 作用下， 以 氯苯 为溶剂， 反应 3.0h， 以24.8%的产率得到N-(3-chlorophenyl)-4-methoxybenzenecarbothioamide
  参考文献：
  名称：

  Synthesis, anticancer activity and docking of some substituted benzothiazoles as tyrosine kinase inhibitors

  摘要：

  Protein tyrosine kinases occupy a central position in the control of cellular proliferation and its inactivation might lead to the discovery of a new generation anticancer compounds. Substituted benzothiazoles have been found to mimic the ATP-competitive binding of genistein and quercetin to tyrosine kinase. A series of novel 2-phenyl-1,3-benzothiazoles were synthesized and characterised by IR, H-1 NMR and mass spectroscopy. All the compounds were tested for their anticancer activity against MCF-7 breast cancer cell line with the MTT assay. Most of the compounds showed moderate to good anti-breast cancer activity. Anticancer activity varied with substitution on the benzothiazole nucleus with halogens and at 4 position, substitution of the 2-phenyl moiety with methyl and methoxy groups was also explored. Among the compounds tested with MTT assay, mono fluoro substitution on benzothiazole nucleus and 4'-methyl variations at 2-phenyl position demonstrated highest percent growth inhibition of MCF-7 cells. Docking studies of the synthesised compounds was done on EGFR using GRIP batch docking method to study their observed activity. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jmgm.2010.04.003
• 作为产物：
  描述：

  4-甲氧基苯甲酰胺 、 1-氯-3-碘苯 在 copper(I) oxide 、 potassium phosphate 、 四丙基溴化铵 作用下， 以 水 为溶剂， 反应 24.0h， 以50%的产率得到N-(3-氯苯基)-4-甲氧基苯酰胺
  参考文献：
  名称：

  水中酰胺与芳基卤化物的高效无配位铜催化N-芳基化

  摘要：

  已经开发了一种方便有效的方案，用于在水中使用无配位体的氧化铜（I）催化剂将酰胺和芳基碘化物交叉偶联。各种酰胺衍生物以中等至良好的产率（高达88％）提供了相应的N-芳基化产物。

  DOI：

  10.1016/j.tetlet.2011.01.003

文献信息

• Kinetics and mechanism of the aminolysis of benzoic anhydrides
  作者：Byung Choon Lee、Ji Hyun Yoon、Cheal Gyu Lee、Ikchoon Lee

  DOI：10.1002/poc.610070602

  日期：1994.6

  the latter, indicate that the reaction proceeds by a frontside SN2 attack on either one of the caronyl carbon with a strong interaction between the nucleophile (X) and the leaving group (Z). The mechanism is also supposed by the trends in the activation parameters.

  在甲醇中研究了苯环被苯环取代的苯甲酸酐的亲核取代反应。产物形成步骤与限速步骤一致，因此可以分解竞争反应途径的两个速率常数k XZ和k XZ。两个交叉相互作用常数，ρ XY和ρ XY，尤其是一个异常大的幅度后者的，表明该反应的进行通过前侧小号Ñ 2攻击的caronyl碳与亲核试剂之间的强烈的相互作用的任一个（X ）和离去组（Z）。激活参数的趋势也可以推测这种机制。
• Accelerated Discovery in Photocatalysis using a Mechanism-Based Screening Method
  作者：Matthew N. Hopkinson、Adrián Gómez-Suárez、Michael Teders、Basudev Sahoo、Frank Glorius

  DOI：10.1002/anie.201600995

  日期：2016.3.18

  Herein, we report a conceptually novel mechanism‐based screening approach to accelerate discovery in photocatalysis. In contrast to most screening methods, which consider reactions as discrete entities, this approach instead focuses on a single constituent mechanistic step of a catalytic reaction. Using luminescence spectroscopy to investigate the key quenching step in photocatalytic reactions, an

  本文中，我们报告了一种概念上新颖的基于机理的筛选方法，可加快光催化作用中的发现。与大多数将反应视为离散实体的筛选方法相反，该方法侧重于催化反应的单个组成机理步骤。使用发光光谱研究光催化反应中的关键淬灭步骤，对100种化合物的初步筛选导致发现了两种有前途的底物类别。此外，第二个更集中的屏幕提供了机械见解，可用于开发概念验证反应。总体而言，这种快速而直接的方法既促进了发现，也促进了新的光促进反应的发展，并表明基于机制的筛选策略可能成为寻找新反应性的有用工具。
• Amidines. IV. Hydrolysis of N1-acyl derivatives of N1,N2-diarylamidine in carboxylate buffer solution.
  作者：Machiko ONO、Kazuhide HAYAKAWA、Shinzo TAMURA

  DOI：10.1248/cpb.38.1176

  日期：——

  In the hydrolysis of N1-benzoyl-N1, N2-diphenylacetamidine (1) in carboxylate buffer solutions, nucleophilic attack of the catalytic acid was proved to take place at the amide carbonyl carbon (pathway d) and presumably also at the amidine central carbon (pathway e) in parallel to the normal hydrolysis processes. Mixed acid anhydride and N1, N2-diphenylacetamidine were formed by pathway d, and the former reacted with aniline formed by further hydrolysis of the latter to give two N-acylanilines. In parallel with this process, the mixed anhydride reacts with water to give two carboxylic acids. In this case, carboxylic acid acts as a nucleophilic catalyst.The reaction of 1 and p-methoxybenzoic acid under anhydrous conditions gave products derived from the attack of p-methoxybenzoate ion at both amide carbonyl and amidine central carbons.Hydrolysis of N1-benzoyl-N-1, N2-diphenylformamidine (7) in acetate buffer solution proceeded mainly through the ordinary hydrolysis pathway. Formation of a small amount of acetanilide implies that the reaction proceeds through pathway d or e to a small extent.In hydrolysis of N1-tosyl-N1, N2-di(p-methylphenyl)acetamidine (6b) in glycolate buffer solution, a small amount of N-(acetoxyacetyl)-p-toluidine was formed together with the ordinary hydrolysis products. This implies that the reaction proceeds through pathway e to a small extent.

  在N1-苯甲酰-N1, N2-二苯基乙酰胺（1）在羧酸盐缓冲溶液中的水解过程中，催化酸的亲核攻击被证明发生在酰胺羰基碳（路径d），并且推测同时也在氨基中央碳上发生（路径e），与常规水解过程并行。通过路径d形成了混合酸酐和N1, N2-二苯基乙酰胺，而前者与通过对后者的进一步水解生成的苯胺反应，生成两个N-酰氨基苯。他们同时，混合酸酐与水反应，生成两个羧酸。在这种情况下，羧酸作为亲核催化剂。N1-苯甲酰-N-1, N2-二苯基甲酰胺（7）在醋酸盐缓冲液中的水解主要通过普通水解路径进行。少量乙酰苯胺的形成意味着反应在一定程度上通过路径d或e进行。在N1-对甲苯磺酰-N1, N2-二（对甲基苯基）乙酰胺（6b）在乙二醇酸盐缓冲液中的水解过程中，除了普通水解产物外，还形成了少量N-(乙酰氧乙酰)-对甲基苯胺。这意味着反应在一定程度上通过路径e进行。
• BENZAMIDE DERIVATIVES AND THEIR USE FOR TREATING CNS DISORDERS
  申请人：Galley Guido

  公开号：US20090036420A1

  公开（公告）日：2009-02-05

  The present invention relates to methods of treating CNS disorders with a compound of formula I wherein X, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 are as defined in the specification and pharmaceutically acceptable acid addition salts thereof.

  本发明涉及使用式I中的化合物治疗中枢神经系统疾病的方法，其中X、R1、R2、R3、R4、R5、R6、R7和R8如说明书中所定义，并且包括药学上可接受的酸盐。
• METHOD FOR PRODUCING BIARYL COMPOUND
  申请人：Sato Koichi

  公开号：US20100087680A1

  公开（公告）日：2010-04-08

  A method for producing a biaryl compound, comprising reacting an aromatic organic compound with at least one compound selected from the group consisting of aromatic organoboron compounds and boroxine compounds, in the presence of a zero-valent nickel catalyst, phosphine ligand and base.

  一种制备双芳基化合物的方法，包括在零价镍催化剂、膦配体和碱的存在下，将芳香有机化合物与选自芳香基有机硼化合物和硼氧化物化合物组的至少一种化合物反应。