N-(2,4-dimethoxyphenyl)picolinamide | 804484-48-8

• 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: N-(2,4-dimethoxyphenyl)picolinamide
• 英文别名: N-2,4-dimethoxide-Ph-picolinamide；N-(2,4-dimethoxyphenyl)pyridine-2-carboxamide
• CAS: 804484-48-8
• 化学式: C₁₄H₁₄N₂O₃
• 分子量: 258.277
• InChiKey: VRBVHWAWRHYPSI-UHFFFAOYSA-N

物化性质

• 沸点：
  348.1±37.0 °C(Predicted)
• 密度：
  1.232±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  60.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  甲醇 、 N-(2-甲氧基苯基)-2-吡啶羧酰胺 在 过氧乙酸 、 4-碘甲苯 、 platinum on carbon 作用下， 反应 12.0h， 以70%的产率得到N-(2,4-dimethoxyphenyl)picolinamide
  参考文献：
  名称：

  固体支持的Pt催化芳基胺的远程CH醚化：合成芳族醚的简单实用方法

  摘要：

  本文通过使用固体负载的Pt催化剂开发了一种简单实用的方法，用于将芳基胺与醇直接进行远程CH醚化反应，从而为合成芳族醚提供了一种有价值的方法。可以容易地从反应混合物中回收催化剂，并重复使用六次而不会明显失去活性。对照实验表明，自由基途径参与了这种转化。

  DOI：

  10.1016/j.catcom.2019.105722

文献信息

• Green alternative solvents for the copper-catalysed arylation of phenols and amides
  作者：Carlo Sambiagio、Rachel H. Munday、A. John Blacker、Stephen P. Marsden、Patrick C. McGowan

  DOI：10.1039/c6ra02265k

  日期：——

  for the Cu-catalysed arylation of phenols and amides is reported. Alkyl acetates proved to be efficient solvents in the catalytic processes, and therefore excellent alternatives to the typical non-green solvents used for Cu-catalysed arylation reactions. Solvents such as isosorbide dimethyl ether (DMI) and diethyl carbonate also appear to be viable possibilities for the arylation of phenols. Finally

  报道了使用绿色有机溶剂进行铜催化的苯酚和酰胺基芳基化的研究。乙酸烷基酯被证明是催化过程中的有效溶剂，因此是用于Cu催化的芳基化反应的典型非绿色溶剂的极佳替代品。诸如异山梨醇二甲醚（DMI）和碳酸二乙酯之类的溶剂似乎也可以用于酚的芳基化。最后，报道了一种新颖的铜催化的酰基转移方法。
• Platinum(<scp>ii</scp>)-catalyzed selective <i>para</i> C–H alkoxylation of arylamines through a coordinating activation strategy
  作者：Jiabin Shen、Jun Xu、Heng Cai、Chao Shen、Pengfei Zhang

  DOI：10.1039/c8ob02942c

  日期：——

  A highly efficient method to selectively install alkoxy onto the para position of arylamines via a coordinating activation strategy has been reported. Various substrates are compatible, providing the corresponding products in good to excellent yields. This strategy gives an efficient and practical solution for the synthesis of unsymmetrical aryl ethers. A free radical pathway mechanism is advised for

  已经报道了通过配位活化策略将烷氧基选择性地安装在芳胺的对位上的高效方法。各种基材都是兼容的，从而以良好至极好的产量提供了相应的产品。该策略为合成不对称芳基醚提供了一种高效实用的解决方案。建议使用自由基途径机制进行转化。
• Transition-metal free oxidative C–H etherification of acylanilines with alcohols through a radical pathway
  作者：Xiaobo Xu、Zhengzhou Chu、Chengcai Xia

  DOI：10.1039/c9ob01224a

  日期：——

  for the synthesis of methyl/ethyl aryl ether via oxidative C-H etherification of acylanilines with alcohols has been developed. Various acylanilines are compatible under standard conditions, giving the corresponding products in moderate to good yields. This strategy avoids transition-metal catalyst and excessive alcohol, providing a simple and reliable alternative method for the synthesis of methyl/ethyl

  已经开发了一种无过渡金属的方法，该方法用于通过酰基苯胺与醇的氧化CH醚化合成甲基/乙基芳基醚。各种酰基苯胺在标准条件下均相容，从而使相应的产品收率适中至良好。该策略避免了过渡金属催化剂和过量的醇，为合成甲基/乙基芳基醚提供了一种简单可靠的替代方法。对照实验表明，这种转化涉及一种根本的机制。
• Amide Linkage Isomerism As an Activity Switch for Organometallic Osmium and Ruthenium Anticancer Complexes
  作者：Sabine H. van Rijt、Andrew J. Hebden、Thakshila Amaresekera、Robert J. Deeth、Guy J. Clarkson、Simon Parsons、Patrick C. McGowan、Peter J. Sadler

  DOI：10.1021/jm900731j

  日期：2009.12.10

  We show that the binding mode adopted by picolinamide derivatives in organometallic Os-II and Ru-II half-sandwich complexes can lead to contrasting cancer cell cytotoxicity. N-Phenyl picolinamide derivatives (XY) in Os-II (1, 3-5, 7, 9) and Ru-II (2, 6, 8, 10) complexes [(eta(6)-arene)(Os/Ru)(XY)Cl](n+), where arene = p-cymene (1-8, 10) or biphenyl (9),can act as N,N- or N,O-donors. Electron-withdrawing substituents on the phenyl ring resulted in N,N-coordination and electron-donating substituents in N,O-coordination. Dynamic interconversion between N,O and N,N configurations can occur in solution and is time- and temperature- (irreversible) as well as pH-dependent (reversible), The neutral N,N-coordinated compounds (1-5 and 9) hydrolyzed rapidly (t(1/2) <= min), exhibited significant (32-70%) and rapid binding to guanine, but no binding to adenine. The N,N-coordinated compounds 1, 3, 4, and 9 exhibited significant activity against colon, ovarian,and cisplatin-resistant ovarian human cancer cell lines (3 >> 4 > 1 > 9). In contrast, N,O-coordinated complexes 7 and 8 hydrolyzed slowly, did not bind to guanine or adenine, and were nontoxic.