6-(4-bromophenyl)-4-(N-(4-methoxyphenyl)benzamido)pyridin-3-yl benzoate | 1426821-61-5

• 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: 6-(4-bromophenyl)-4-(N-(4-methoxyphenyl)benzamido)pyridin-3-yl benzoate
• 英文别名: [4-(N-benzoyl-4-methoxyanilino)-6-(4-bromophenyl)pyridin-3-yl] benzoate
• CAS: 1426821-61-5
• 化学式: C₃₂H₂₃BrN₂O₄
• 分子量: 579.45
• InChiKey: CUSQBSMMVOZKKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  39
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  68.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-(N-(4-methoxyphenyl)benzamido)-6-phenylpyridin-3-yl benzoate 在 zinc trifluoromethanesulfonate 、 臭氧 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 5.25h， 生成 6-(4-bromophenyl)-4-(N-(4-methoxyphenyl)benzamido)pyridin-3-yl benzoate
  参考文献：
  名称：

  Synthesis of Substituted Pyridines from Cascade [1 + 5] Cycloaddition of Isonitriles to N-Formylmethyl-Substituted Enamides, Aerobic Oxidative Aromatization, and Acyl Transfer Reaction

  摘要：

  A novel strategy for de novo synthesis of pyridines featuring an unprecedented a-addition of aldehyde and enamide to isonitrile as a key step is described. Under mild conditions, a cascade reaction involving Zn(OTf)(2)-promoted [1 + 5] cycloaddition of isonitrile with N-formylmethyl-substituted enamide, facile aerobic oxidative aromatization and intermolecular acyl transfer from the pyridinium nitrogen to the 5-hydroxy oxygen, and finally acylation of the 4-amino group by an external acyl chloride efficiently afforded 2-substituted 4-acylamino-5-acyloxypyridines in good to excellent yields.

  DOI：

  10.1021/ja401701x

文献信息

• Exploring tertiary enamides as versatile synthons in organic synthesis
  作者：Mei-Xiang Wang

  DOI：10.1039/c4cc10327k

  日期：——

  Tertiary enamides have long been thought of as stable and marginally valuable enamine variants in synthesis. This notion has been challenged, however, in recent years. Enabling the regulation of the cross-conjugation system of the tertiary enamides has been successfully shown to enhance delocalization of the nitrogen lone-pair electrons into a carbon-carbon double, thereby reinvigorating the enaminic

  长期以来一直认为叔酰胺是合成中稳定的和边际上有价值的烯胺变体。但是，近年来，这一概念受到了挑战。已成功地显示出使叔酰胺的交叉缀合系统的调节能够增强氮孤对电子的离域化为碳-碳双键，从而使叔酰胺的烯胺反应性恢复活力。在本文中，我总结了叔酰胺类化合物亲核反应探索的最新进展及其在天然产物和具有生物学和药学意义的杂环化合物的合成中的应用，主要侧重于我们自己的工作。
• Synthesis of Substituted Pyridines from Cascade [1 + 5] Cycloaddition of Isonitriles to <i>N</i>-Formylmethyl-Substituted Enamides, Aerobic Oxidative Aromatization, and Acyl Transfer Reaction
  作者：Chuan-Hu Lei、De-Xian Wang、Liang Zhao、Jieping Zhu、Mei-Xiang Wang

  DOI：10.1021/ja401701x

  日期：2013.3.27

  A novel strategy for de novo synthesis of pyridines featuring an unprecedented a-addition of aldehyde and enamide to isonitrile as a key step is described. Under mild conditions, a cascade reaction involving Zn(OTf)(2)-promoted [1 + 5] cycloaddition of isonitrile with N-formylmethyl-substituted enamide, facile aerobic oxidative aromatization and intermolecular acyl transfer from the pyridinium nitrogen to the 5-hydroxy oxygen, and finally acylation of the 4-amino group by an external acyl chloride efficiently afforded 2-substituted 4-acylamino-5-acyloxypyridines in good to excellent yields.