4-methoxy-N-phenylpyridin-2-amine | 1570075-45-4

• 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-methoxy-N-phenylpyridin-2-amine
• CAS: 1570075-45-4
• 化学式: C₁₂H₁₂N₂O
• 分子量: 200.24
• InChiKey: IIZXFWPNAQXQTL-UHFFFAOYSA-N

物化性质

• 沸点：
  334.0±27.0 °C(Predicted)
• 密度：
  1.159±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 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：
  34.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-methoxy-N-phenylpyridin-2-amine 在 叔丁基过氧化氢 、 palladium diacetate 、 potassium carbonate 、 三氟甲烷磺酸甲酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲苯 为溶剂， 反应 60.0h， 生成 2-氨基二苯甲酮
  参考文献：
  名称：

  使用4-甲氧基-2-吡啶基作为可移动的导向基团，钯催化苯胺的后期邻位-C-H键芳构化

  摘要：

  通过使用乙酸钯（II），叔丁基氢过氧化物和1,4-二恶烷，苯胺与芳基醛的晚期邻位C-H键芳基化的合成方法导致了多种邻位芳基化的苯胺分别作为催化剂，氧化剂和溶剂。一个Ñ -phenylpyridin -2-胺钯化合物被分离和表征通过X射线晶体学。进行了控制实验，自由基捕获实验和动力学同位素效应实验，以支持所提出的反应机理。成功开发了基于已开发方法的2-氨基二苯甲酮和9（10 H）-ac啶酮的合成方法。

  DOI：

  10.1021/acs.organomet.9b00119
• 作为产物：
  描述：

  溴苯 、 2-氨基-4-甲氧基吡啶 在 copper(l) iodide 、 potassium tert-butylate 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以85%的产率得到4-methoxy-N-phenylpyridin-2-amine
  参考文献：
  名称：

  Ligand free copper-catalyzed N-arylation of heteroarylamines

  摘要：

  DOI：

  10.1016/j.tetlet.2014.11.002

文献信息

• Palladium(II)-Catalyzed Direct Ortho Arylation of 4-Methyl-<i>N</i>-phenylpyridin-2-amines via C–H Activation/C–C Coupling and Synthetic Applications
  作者：Jean-Ho Chu、Hao-Ping Huang、Wen-Ting Hsu、Shih-Tien Chen、Ming-Jung Wu

  DOI：10.1021/om401195w

  日期：2014.3.10

  The direct ortho arylation of 4-methyl-N-phenylpyridin-2-amines via palladium(II)-catalyzed C-H activation is described. Treatment of 4-methyl-N-phenylpyridin-2-amine with potassium aryltrifluoroborate using 10 mol % of palladium(II) acetate as the catalyst, 2 equiv of copper(II) acetate as the oxidant, and 1 equiv of p-benzoquinone in tert-butyl alcohol gave ortho-arylated products in modest to excellent yields. This reaction shows good functional group compatibility. A series of H-1 NMR titration experiments and controlled experiments elucidating the reaction mechanism were carried out. The key intermediate, 4-methyl-N-phenylpyridin-2-amine palladacycle, was isolated and characterized by X-ray crystallography. The advanced transformations of ortho-phenylated 4-methyl-N-phenylpyridin-2-amine to N-(4-methylpyridin-2-yl)-9H-carbazole, biphenyl-2-amine, and 3-methyl-6-phenylpyrido[1,2-a]benzimidazole were successfully demonstrated as potential synthetic applications.
• PYRIDINE COMPOUNDS AND THEIR PHARMACEUTICAL USE
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP1157022A1

  公开（公告）日：2001-11-28
• [EN] PYRIDINE COMPOUNDS AND THEIR PHARMACEUTICAL USE<br/>[FR] COMPOSES PYRIDINE ET LEUR UTILISATION PHARMACEUTIQUE
  申请人：FUJISAWA PHARMACEUTICAL CO

  公开号：WO2000049015A1

  公开（公告）日：2000-08-24

  A compound of formula (I) wherein each symbol is as defined in the specification, and pharmaceutically acceptable salts thereof. The compound (I) of the present invention and pharmaceutically acceptable salts thereof possess a strong inhibitory activity on the production of nitric oxide (NO), and are useful for prevention and/or treatment of NOS(nitric oxide synthase)-mediated diseases such as adult respiratory distress syndrome, myocarditis, synovitis, septic shock, insulin-dependent diabetes mellitus, ulcerative colitis, cerebral infarction, rheumatoid arthritis, osteoarthritis, osteoporosis, systemic lupus erythematosus, rejection by organ transplantation, asthma, pain, ulcer, and the like in human being and animals.
• Palladium-Catalyzed Late-Stage <i>ortho</i>-C–H Bond Aroylation of Anilines Using 4-Methoxy-2-pyridinyl as a Removable Directing Group
  作者：Jean-Ho Chu、Meng-Fan Chiang、Chin-Wei Li、Zhe-Hong Su、Shao-Chi Lo、Ming-Jung Wu

  DOI：10.1021/acs.organomet.9b00119

  日期：2019.5.13

  A synthetic methodology for the late-stage ortho-C–H bond aroylation of anilines with aryl aldehydes led to a variety of ortho-aroylated anilines by the use of palladium(II) acetate, tert-butyl hydroperoxide, and 1,4-dioxane as the catalyst, oxidant, and solvent, respectively, is presented. An N-phenylpyridin-2-amine palladacycle was isolated and characterized by X-ray crystallography. Controlled experiments

  通过使用乙酸钯（II），叔丁基氢过氧化物和1,4-二恶烷，苯胺与芳基醛的晚期邻位C-H键芳基化的合成方法导致了多种邻位芳基化的苯胺分别作为催化剂，氧化剂和溶剂。一个Ñ -phenylpyridin -2-胺钯化合物被分离和表征通过X射线晶体学。进行了控制实验，自由基捕获实验和动力学同位素效应实验，以支持所提出的反应机理。成功开发了基于已开发方法的2-氨基二苯甲酮和9（10 H）-ac啶酮的合成方法。
• Ligand free copper-catalyzed N-arylation of heteroarylamines
  作者：Deping Wang、Daizhi Kuang、Fuxing Zhang、Yang Liu、Shunhua Ning

  DOI：10.1016/j.tetlet.2014.11.002

  日期：2014.12