N-(4-甲氧基苯基)异烟脒 | 23565-15-3

• 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-(4-甲氧基苯基)异烟脒
• 英文名称: N-(4-methoxyphenyl)isonicotinimidamide
• 英文别名: Methoxy-4'-phenyl-pyridino-4-amidin；N-(p-Methoxyphenyl)isonicotinamidine；N'-(4-methoxyphenyl)pyridine-4-carboximidamide
• CAS: 23565-15-3
• 化学式: C₁₃H₁₃N₃O
• 分子量: 227.266
• InChiKey: IHSQITMFXQQHOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 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：
  60.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933399090

反应信息

• 作为产物：
  描述：

  4-氯苯甲醚 、 4-amidinopyridine hydrochloride 在 tris-(dibenzylideneacetone)dipalladium(0) 、 2-二叔丁基膦-2′,4′,6′-三异丙基-3,6-二甲氧基-1,1′-联苯 、 caesium carbonate 作用下， 以 叔丁醇 为溶剂， 反应 2.02h， 以67%的产率得到N-(4-甲氧基苯基)异烟脒
  参考文献：
  名称：

  Palladium-Catalyzed N-Monoarylation of Amidines and a One-Pot Synthesis of Quinazoline Derivatives

  摘要：

  A method for the Pd-catalyzed N-arylation of both aryl and alkyl amidines with a wide range of aryl bromides, chlorides, and triflates is described. The reactions proceed in short reaction times and with excellent selectivity for monoarylation. A one-pot synthesis of quinazoline derivatives, via addition of an aldehyde to the crude reaction mixture following Pd-catalyzed N-arylation, is also demonstrated.

  DOI：

  10.1021/ol301700y

文献信息

• Synthesis and antiinflammatory activity of N1-(substituted phenyl)pyridinecarboxamidines.
  作者：TAKUZO HISANO、MASANOBU TASAKI、KONOSUKE TSUMOTO、TOSHIKAZU MATSUOKA、MASATAKA ICHIKAWA

  DOI：10.1248/cpb.31.2484

  日期：——

  A series of N1-(substituted phenyl) pyridinecarboxamidines was synthesized by the condensation of substituted anilines with cyanopyridines in the presence of aluminum chloride or sodium amide and these compounds were evaluated for antiinflammatory activity by the carrageenin-induced rat paw edema assay. In the synthesis of N1-alkoxyphenyl pyridinecarboxamidines, it was found that o-alkoxyanilines reacted with aluminum chloride to afford o-aminophenol, while m- and p-alkoxyanilines were scarcely dealkylated. Sodium amide was successfully used for the condensation of o-alkoxyanilines with cyanopyridines. Among several active derivatives, N1-(2, 4-dichlorophenyl) pyridinecarboxamidine and N1-(4-chlorophenyl)-pyridinecarboxamidine exhibited significant antiinflammatory activities.

  通过在氯化铝或钠胺的存在下，将取代的芳香胺与氰基吡啶缩合，合成了一系列N1-(取代苯基)吡啶羧氨基。在合成N1-烷氧基苯基吡啶羧氨基的过程中，发现邻烷氧基芳香胺与氯化铝反应生成邻氨基酚，而间位和对位的烷氧基芳香胺几乎没有去烷基化。成功地使用钠胺将邻烷氧基芳香胺与氰基吡啶进行缩合。在几种活性衍生物中，N1-(2,4-二氯苯基)吡啶羧氨基和N1-(4-氯苯基)吡啶羧氨基表现出显著的抗炎活性。
• HISANO, TAKUZO;TASAKI, MASANOBU;MATSUOKA, TOSHIKAZU;ICHIKAWA, MASATAKA, ORG. PREP. AND PROCED. INT., 1982, 14, N 6, 399-403
  作者：HISANO, TAKUZO、TASAKI, MASANOBU、MATSUOKA, TOSHIKAZU、ICHIKAWA, MASATAKA

  DOI：——

  日期：——
• HISANO, TAKUZO;TASAKI, MASANOBU;TSUMOTO, KONOSUKE;MATSUOKA, TOSHIKAZU;ICH+, CHEM. AND PHARM. BULL., 1983, 31, N 7, 2484-2490
  作者：HISANO, TAKUZO、TASAKI, MASANOBU、TSUMOTO, KONOSUKE、MATSUOKA, TOSHIKAZU、ICH+

  DOI：——

  日期：——
• Palladium-Catalyzed N-Monoarylation of Amidines and a One-Pot Synthesis of Quinazoline Derivatives
  作者：Meredeth A. McGowan、Camille Z. McAvoy、Stephen L. Buchwald

  DOI：10.1021/ol301700y

  日期：2012.7.20

  A method for the Pd-catalyzed N-arylation of both aryl and alkyl amidines with a wide range of aryl bromides, chlorides, and triflates is described. The reactions proceed in short reaction times and with excellent selectivity for monoarylation. A one-pot synthesis of quinazoline derivatives, via addition of an aldehyde to the crude reaction mixture following Pd-catalyzed N-arylation, is also demonstrated.