4-methoxypicolinanilide | 126798-20-7

• 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: 4-methoxypicolinanilide
• 英文别名: 2-Pyridinecarboxamide,4-methoxy-n-phenyl-；4-methoxy-N-phenylpyridine-2-carboxamide
• CAS: 126798-20-7
• 化学式: C₁₃H₁₂N₂O₂
• 分子量: 228.25
• InChiKey: YYGKAVCAJZOCMI-UHFFFAOYSA-N

物化性质

• 沸点：
  319.1±27.0 °C(Predicted)
• 密度：
  1.230±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 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：
  51.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-methoxypicolinanilide 在 正丁基锂 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成
  参考文献：
  名称：

  Heteroaryl-Fused 2-Phenylisothiazolone Inhibitors of Cartilage Breakdown

  摘要：

  The synthesis, biological evaluation, and structure-activity relationships of a series of N-phenyl heteroaryl-fused isothiazolones are described. These isothiazolones have been shown to exhibit potent, dose-dependent inhibition of IL-1 beta-induced breakdown of proteoglycan in a cartilage organ culture assay. This effect is likely due to inhibition of MMP activation and a consequent reduction in MMP activity following IL-1 beta stimulation. Thus these compounds potentially represent simple, non-peptidic disease-modifying agents for the treatment of arthritic diseases. To examine the effects of structure on in vitro activity, three general features of the molecules were varied, substituents on the pendant N-phenyl group, the position of ring fusion to the isothiazolone, and substituents on the fused ring peri to the isothiazolone sulfur.

  DOI：

  10.1021/jm00045a012
• 作为产物：
  描述：

  4-硝基吡啶-2-甲酸 1-氧化物 在 三乙胺 、 三氯化磷 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 5.5h， 生成 4-methoxypicolinanilide
  参考文献：
  名称：

  有机锂及相关试剂在合成中的应用。第7部分。4-甲氧基吡啶啉-和2-甲氧基异烟碱-苯胺的合成和金属化。制备2，3，4-三取代吡啶的有用方法

  摘要：

  描述了4-甲氧基吡啶啉-和2-甲氧基异烟酰胺-苯胺的合成和金属化，作为将吡啶甲酸和异烟酸酸区域特异性转化为2、3、4-三取代的吡啶的方法。所得的C 3-烷基化衍生物经历平滑的酸催化转化为相应的吡啶酮。

  DOI：

  10.1016/s0040-4020(01)89209-7

文献信息

• Copper-Catalyzed Remote <i>para</i> -C−H Functionalization of Anilines with Sodium and Lithium Sulfinates
  作者：Shuai Liang、Michael Bolte、Georg Manolikakes

  DOI：10.1002/chem.201605101

  日期：2017.1.1

  A copper‐catalyzed, cross‐dehydrogenative coupling of anilines with sodium and lithium sulfinates was developed. By using a cooperative reaction system with Mn(OAc)3 as stoichiometric co‐oxidant a highly selective para‐functionalization of anilines was accomplished. Various functional groups were tolerated and the desired products were obtained in high yields. This method not only provides a novel

  已开发出铜催化的苯胺与亚磺酸钠和亚硫酸锂的交叉脱氢偶联反应。通过使用以Mn（OAc）3作为化学计量助氧化剂的协同反应系统，苯胺的高度选择性对官能化得以实现。耐受各种官能团，并以高收率获得所需产物。该方法不仅为芳基砜的合成提供了一种新颖的方法，而且还可能为开发铜催化的对位选择性CH官能团提供新的机会。
• Copper-Catalyzed Carboxamide-Directed <i>Ortho</i> Amination of Anilines with Alkylamines at Room Temperature
  作者：Qiong Li、Shu-Yu Zhang、Gang He、Zhaoyan Ai、William A. Nack、Gong Chen

  DOI：10.1021/ol500464x

  日期：2014.3.21

  In this report, a highly efficient method for the room temperature installation of alkyl amino motifs onto the ortho position of anilines via Cu-catalyzed carboxamide-directed amination with alkylamines is described. This method offers a practical solution for the rapid synthesis of complex arylamines from simple starting materials and enables new planning strategies for the construction of arylamine-containing pharmacophores. A single electron transfer (SET)-mediated mechanism is proposed.
• Heteroaryl-Fused 2-Phenylisothiazolone Inhibitors of Cartilage Breakdown
  作者：Stephen W. Wright、Joseph J. Petraitis、Matthew M. Abelman、Douglas G. Batt、Lori L. Bostrom、Ronald L. Corbett、Carl P. Decicco、Susan V. Di Meo、Bruce Freimark

  DOI：10.1021/jm00045a012

  日期：1994.9

  The synthesis, biological evaluation, and structure-activity relationships of a series of N-phenyl heteroaryl-fused isothiazolones are described. These isothiazolones have been shown to exhibit potent, dose-dependent inhibition of IL-1 beta-induced breakdown of proteoglycan in a cartilage organ culture assay. This effect is likely due to inhibition of MMP activation and a consequent reduction in MMP activity following IL-1 beta stimulation. Thus these compounds potentially represent simple, non-peptidic disease-modifying agents for the treatment of arthritic diseases. To examine the effects of structure on in vitro activity, three general features of the molecules were varied, substituents on the pendant N-phenyl group, the position of ring fusion to the isothiazolone, and substituents on the fused ring peri to the isothiazolone sulfur.
• Application of organolithium and related reagents in synthesis. Part 7. Synthesis and metallion of 4-methoxypicolin- and 2-methoxyisonicotin-anilides. A useful method for preparation of 2, 3, 4-trisubstituted pyridines
  作者：Jan Epsztajn、Adam Bieniek、Mieczysław W. Płotka、Krzysztof Suwald

  DOI：10.1016/s0040-4020(01)89209-7

  日期：1989.1

  The synthesis and metallation of 4-methoxypicolin- and 2-methoxyisonicotin-anilides as a way of regiospecific transformation of picolinic and isonicotinic acids into 2, 3, 4-trisubstituted pyridines, is described. The resulted C3 - alkylated derivatives underwent smooth acid - catalysed conversion into the corresponding pyridones.

  描述了4-甲氧基吡啶啉-和2-甲氧基异烟酰胺-苯胺的合成和金属化，作为将吡啶甲酸和异烟酸酸区域特异性转化为2、3、4-三取代的吡啶的方法。所得的C 3-烷基化衍生物经历平滑的酸催化转化为相应的吡啶酮。