2,6-二氯-N-(4-甲氧基苯基)苯胺 | 30124-19-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2,6-二氯-N-(4-甲氧基苯基)苯胺
• 英文名称: 2,6-dichloro-4'-methoxydiphenylamine
• 英文别名: 2',6'-(dichlorophenyl)-4-(methoxyphenyl)amine；N-(2.6-Dichlorphenyl)-p-anisidin；N-(4-methoxyphenyl)-2,6-dichloro aniline；2,6-Dichloro-N-(4-methoxyphenyl)aniline
• CAS: 30124-19-7
• 化学式: C₁₃H₁₁Cl₂NO
• 分子量: 268.142
• InChiKey: BLFDNLHOYIEHMA-UHFFFAOYSA-N

物化性质

• 沸点：
  346.4±42.0 °C(Predicted)
• 密度：
  1.318±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2922199090

反应信息

• 作为反应物：
  描述：

  2,6-二氯-N-(4-甲氧基苯基)苯胺 在 aluminum (III) chloride 、 水 、 对甲苯磺酸 、 sodium hydroxide 作用下， 反应 9.0h， 生成 2-[(2,6-Dichlorophenyl)amino]-5-hydroxy benzene acetic acid methyl ester
  参考文献：
  名称：

  Diclofenac derivatives with insulin-sensitizing activity

  摘要：

  A series of diclofenac derivatives were synthesized. The insulin-sensitizing activity of 28 new compounds was evaluated in 3T3-L1 cells. The compounds 10a and 10f exhibited similar insulin-sensitizing activity with positive drug rosiglitazone. (C) 2010 Lei Tang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2010.11.008
• 作为产物：
  描述：

  2,2,6,6-四氯环己酮 在 四氯化钛 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 54.0h， 生成 2,6-二氯-N-(4-甲氧基苯基)苯胺
  参考文献：
  名称：

  2,2,6,6-四氯己酮与取代苯胺和氨的反应。邻苯二酚的 5-硝基和 5-氨基类似物的合成

  摘要：

  最近我们开发了一种基于专利 [1] 的新方法，用于合成著名抗炎药邻苯二酚 [2] 的关键产品 2,6-二氯二苯胺的商业化生产。该方法包括在四氯化钛存在下苯胺与 2,2,6,6-四氯环己烷 (I) 的相互作用，然后中间体 N-苯基-2,2,6,6 四氯环己烷亚胺 [3, 4] 的脱氯化氢。原则上，该方案也可用于合成 2,6-二氯二苯胺，在氯未取代的苯环上含有各种取代基，从而获得新的邻苯二酚衍生物。这项工作的目的是研究在oandp-茴香胺和对氨基苯酚的情况下使用该反应的可能性。我们还评估了从 2-吲哚酮衍生物合成取代邻苯二酚的替代方法。在四氯化钛存在下，酮 I 与邻茴香胺的相互作用产生相应的苯胺 (IIa, lib)。电子冲击质谱中分子离子峰的相对强度表明这些化合物的分子保留了四个氯原子。分子离子质量 (339 z) 的值与建议的结构一致。基于 CI 和 HCl 碎片的连续消除以及环己烷环与分

  DOI：

  10.1007/bf02464226

文献信息

• Syntheses and Characterization of the Acyl Glucuronide and Hydroxy Metabolites of Diclofenac
  作者：Jane R. Kenny、James L. Maggs、Xiaoli Meng、Deborah Sinnott、Stephen E. Clarke、B. Kevin Park、Andrew V. Stachulski

  DOI：10.1021/jm030891w

  日期：2004.5.1

  quantities of 2-4 are required and their syntheses and characterization are described here. Key steps were a convenient two-step preparation of aniline 5 from phenol, efficient and selective 6-iodination of amide 18, and high-yielding Ullmann couplings to generate diarylamines 11 and 21. The acyl glucuronide 4 was obtained by Mitsunobu reaction of 1 (free acid) with allyl glucuronate 23 followed by Pd(0) deprotection

  在人类中，常用的非甾体类抗炎药双氯芬酸1的代谢主要产生4'-羟基2、5-羟基3和酰基葡糖醛酸4代谢物。所有这三种代谢物都与这种广泛使用的药物相关的罕见特发性不良反应有关。因此，对于1的机械毒理学研究，需要大量的2-4，并在此描述其合成和表征。关键步骤包括从苯酚方便地分两步制备苯胺5，酰胺18进行高效且选择性的6碘化以及高产率的Ullmann偶联以生成二芳基胺11和21.酰基的葡糖醛酸苷4通过1的Mitsunobu反应获得葡萄糖醛酸23烯丙基酯，然后使用Pd（0）脱保护，使用公开程序的修改方法。我们报告了4的全部特征，并注意到该重要的代谢物已首次以纯净和大量提供。我们还报告了合成代谢产物的代谢命运：2和3在大鼠中是葡萄糖醛酸化的，但在体内和通过醌亚胺中间体的酶促合成中，只有3个形成了谷胱甘肽加合物。通过酶促合成获得先前未描述的3的谷胱甘肽加合物。如氰基硼氢化钠捕获所示，化合物4形成了亚胺连接
• 2-Anilino phenylacetic acid derivatives
  申请人：American Home Products Corporation

  公开号：US05021576A1

  公开（公告）日：1991-06-04

  There are disclosed compounds of the formula ##STR1## wherein R is hydroxy, lower alkoxy or lower alkoxyamino; R.sup.1 is hydrogen or A(CH.sub.2).sub.n O--; R.sup.2 is hydrogen or A(CH.sub.2).sub.n O--, with the proviso that one of R.sup.1 and R.sup.2 is A(CH.sub.2).sub.n O-- and the other is hydrogen; n is 1-2; A is phenoxyethyl, phenoxyphenyl or a group having the formula ##STR2## X is --N-- or ##STR3## Z is ##STR4## R.sup.3 is hydrogen, lower alkyl or phenyl; R.sup.4 is hydrogen or lower alkyl; or R.sup.3 and R.sup.4 taken together form a benzene ring; R.sup.5 is hydrogen or lower alkyl; R.sup.6 is hydrogen, halo or lower alkyl; and the pharmacologically acceptable salts thereof, and their use in the treatment of inflammatory conditions, such as rheumatoid arthritis, ulcerative colitis, psoriasis and other immediate hypersensitivity reactions; in the treatment of leukotriene-mediated naso-bronchial obstructive air-passageway conditions, such as allergic rhinitis, allergic bronchial asthma and the like; and as gastric cytoprotective agents.

  公开了以下式子的化合物：##STR1## 其中 R是羟基，低基氧基或低基氧基氨基; R.sup.1是氢或A(CH.sub.2).sub.n O--; R.sup.2是氢或A(CH.sub.2).sub.n O--，但其中一个为A(CH.sub.2).sub.n O--，另一个为氢; n为1-2; A是苯氧乙基，苯氧苯基或具有以下式子的基团：##STR2## X为--N--或##STR3## Z为##STR4## R.sup.3是氢，低基烷基或苯基; R.sup.4是氢或低基烷基; 或R.sup.3和R.sup.4一起形成苯环; R.sup.5是氢或低基烷基; R.sup.6是氢，卤素或低基烷基; 以及其药学上可接受的盐，并用于治疗炎症疾病，如类风湿性关节炎、溃疡性结肠炎、银屑病和其他即时超敏反应; 用于治疗白三烯介导的鼻支气管阻塞性通气道疾病，如过敏性鼻炎、过敏性支气管哮喘等; 以及作为胃黏膜保护剂。
• 2-anilino phenylacetic acid derivatives as inhibitors of PLA.sub.2 and
  申请人：American Home Products Corporation

  公开号：US05159085A1

  公开（公告）日：1992-10-27

  There are disclosed compounds of the formula ##STR1## wherein R is hydroxy, lower alkoxy or lower alkoxyamino; R.sup.1 is hydrogen or A(CH.sub.2).sub.n O--; R.sup.2 is hydrogen or A(CH.sub.2).sub.n O--, with the proviso that one of R.sup.1 and R.sup.2 is hydrogen; n is 1-2; A is phenoxyethyl, phenoxyphenyl or a group having the formula ##STR2## R.sup.3 is hydrogen, lower alkyl or phenyl; R.sup.4 is hydrogen or lower alkyl; or R.sup.3 and R.sup.4 taken together form a benzene ring; R.sup.5 is hydrogen or lower alkyl; R.sup.6 is hydrogen, halo or lower alkyl; and the pharmacologically acceptable salts thereof, and their use in the treatment of inflammatory conditions, such as rheumatoid arthritis, ulcerative colitis, psoriasis and other immediate hypersensitivity reactions; in the treatment of leukotriene-mediated naso-bronchial obstructive air-passageway conditions, such as allergic rhinitis, allergic bronchial asthma and the like; and as gastic cytoprotective agents.

  公开了以下式子的化合物：##STR1## 其中R为羟基，较低的烷氧基或较低的烷氧基氨基；R.sup.1为氢或A(CH.sub.2).sub.n O--；R.sup.2为氢或A(CH.sub.2).sub.n O--，但其中一个为氢；n为1-2；A为苯氧乙基，苯氧苯基或具有以下式子的基团：##STR2## R.sup.3为氢，较低的烷基或苯基；R.sup.4为氢或较低的烷基；或R.sup.3和R.sup.4一起形成苯环；R.sup.5为氢或较低的烷基；R.sup.6为氢，卤素或较低的烷基；以及其药理学上可接受的盐，并用于治疗炎症病症，例如风湿性关节炎，溃疡性结肠炎，牛皮癣和其他即时超敏反应；用于治疗白三烯介导的鼻支气管阻塞性疾病，例如过敏性鼻炎，过敏性支气管哮喘等；以及作为胃黏膜保护剂。
• 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.
• TW2020/39493
  申请人：——

  公开号：——

  公开（公告）日：——