(2-chloro-6-methyl)diphenylamine | 13504-93-3

• 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: (2-chloro-6-methyl)diphenylamine
• 英文别名: 2-Chlor-6-methyl-diphenylamin；6-Chlor-N-phenyl-o-toluidin；2-chloro-6-methyl-N-phenylaniline
• CAS: 13504-93-3
• 化学式: C₁₃H₁₂ClN
• 分子量: 217.698
• InChiKey: NXHYVXRWKQWGCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  15
• 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：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2-chloro-6-methyl)diphenylamine 在 sodium hydroxide 、 三氯化铝 、 sodium methylate 、 一水合肼 作用下， 以 乙醇 、 乙二醇甲醚 、 水 、 苯 为溶剂， 反应 23.17h， 生成 [o-(2-methyl-6-chloro-anilino)-phenyl]-acetic acid
  参考文献：
  名称：

  Synthesis and quantitative structure-activity relationships of diclofenac analogs

  摘要：

  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.

  DOI：

  10.1021/jm00171a008
• 作为产物：
  描述：

  2,3-二氯甲苯 、 苯胺 在 bis(η3-allyl-μ-chloropalladium(II)) 、 1,2-bis(diphenylphosphino)-1′-(diisopropylphosphino)-4-tert-butylferrocene 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 20.0h， 以49%的产率得到(2-chloro-3-methyl)diphenylamine
  参考文献：
  名称：

  空气稳定的坚固多齿二茂铁基二膦膦酸酯催化形成钯C–N键：苯胺衍生物与二氯芳烃高效选择性偶联的比较研究†

  摘要：

  使用九种不同的二茂铁基膦配体，包括容易获得的1,1'-双（二苯基膦基）二茂铁，DPPF，研究了钯含量低（低于目前使用的5-10 mol％）下苯胺衍生物与二氯芳烃的芳基化作用。电子富集的空气稳定的三齿ferrocenylpolyphosphine 1,2-双（二苯基膦基）-1' - （二异丙基）-4-叔-butylferrocene，L5，在2摩尔％与1摩尔％[的PdCl（采用组合η 3 - C 3 H 5）] 2允许有效和选择性的偶联，而目前这种要求苛刻的底物引发了氯芳烃均偶联和/或脱卤过程。探索了优化系统的范围和局限性，重点关注贫电子的氟苯胺（失活的亲核试剂）和富电子的甲基化和甲氧基化的二氯苯（失活的亲电试剂）。

  DOI：

  10.1039/c4cy00151f

文献信息

• TETRAAZA- OR N2S2- COMPLEXANTS, AND THEIR USE IN RADIODIAGNOSTICS OR RADIOTHERAPY
  申请人：Poniard Pharmaceuticals, Inc.

  公开号：EP0971748B1

  公开（公告）日：2007-02-07
• 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.
• Palladium C–N bond formation catalysed by air-stable robust polydentate ferrocenylphosphines: a comparative study for the efficient and selective coupling of aniline derivatives to dichloroarene
  作者：Mélanie Platon、Julien Roger、Sylviane Royer、Jean-Cyrille Hierso

  DOI：10.1039/c4cy00151f

  日期：——

  The arylation of aniline derivatives with dichloroarenes under a low palladium content (below the currently used 5 to 10 mol%) was studied using nine different ferrocenylphosphine ligands, including the easily accessible 1,1′-bis(diphenylphosphino)ferrocene, DPPF. The electron-enriched air-stable tridentate ferrocenylpolyphosphine 1,2-bis(diphenylphosphino)-1′-(diisopropylphosphino)-4-tert-butylferrocene

  使用九种不同的二茂铁基膦配体，包括容易获得的1,1'-双（二苯基膦基）二茂铁，DPPF，研究了钯含量低（低于目前使用的5-10 mol％）下苯胺衍生物与二氯芳烃的芳基化作用。电子富集的空气稳定的三齿ferrocenylpolyphosphine 1,2-双（二苯基膦基）-1' - （二异丙基）-4-叔-butylferrocene，L5，在2摩尔％与1摩尔％[的PdCl（采用组合η 3 - C 3 H 5）] 2允许有效和选择性的偶联，而目前这种要求苛刻的底物引发了氯芳烃均偶联和/或脱卤过程。探索了优化系统的范围和局限性，重点关注贫电子的氟苯胺（失活的亲核试剂）和富电子的甲基化和甲氧基化的二氯苯（失活的亲电试剂）。