N-{3-[2-(2-hydroxyphenyl)-2-methoxyethyl]-4-methoxyphenyl}benzamide

• 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-{3-[2-(2-hydroxyphenyl)-2-methoxyethyl]-4-methoxyphenyl}benzamide
• 英文别名: N-[3-[2-(2-hydroxyphenyl)-2-methoxyethyl]-4-methoxyphenyl]benzamide
• 化学式: C₂₃H₂₃NO₄
• 分子量: 377.44
• InChiKey: RRSRTQLGCXVLIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-benzoylbenzoquinone imine dimethyl ketal 、 乙酰苯 在 S-联萘酚磷酸酯 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以52%的产率得到N-{3-[2-(2-hydroxyphenyl)-2-methoxyethyl]-4-methoxyphenyl}benzamide
  参考文献：
  名称：

  Organocatalytic Chemo- and Regioselective Oxyarylation of Styrenes via a Cascade Reaction: Remote Activation of Hydroxyl Groups

  摘要：

  The first organocatalytic oxyarylation of styrenes has been established through a cascade of vinylogous Michael adclition/alkoxyl transfer reactions of o- or p-hydroxylstyrenes with quinone imine ketals. The process leads to a highly chemo- and regioselective oxyarylation of styrenes and provides access to m-alkylated anilines in generally high yields and excellent diastereoselectivity (up to 99% yield, >95:5 dr). An investigation of the reaction pathway revealed that the existence and position of the hydroxyl group of styrene played crucial roles in the cascade reaction, suggesting that the two reactants were simultaneously activated by binaphthyl-derived phosphoric acid via hydrogen bonding interactions and long-distance conjugative effects. In addition, the activating group of the hydroxyl functionality in the products can be easily removed or transformed, demonstrating the applicability and utility of this strategy in styrene oxyarylation and in the synthesis of styrene-based compounds.

  DOI：

  10.1021/jo500859b

文献信息

• Organocatalytic Chemo- and Regioselective Oxyarylation of Styrenes via a Cascade Reaction: Remote Activation of Hydroxyl Groups
  作者：Yu-Chen Zhang、Fei Jiang、Shu-Liang Wang、Feng Shi、Shu-Jiang Tu

  DOI：10.1021/jo500859b

  日期：2014.7.3

  The first organocatalytic oxyarylation of styrenes has been established through a cascade of vinylogous Michael adclition/alkoxyl transfer reactions of o- or p-hydroxylstyrenes with quinone imine ketals. The process leads to a highly chemo- and regioselective oxyarylation of styrenes and provides access to m-alkylated anilines in generally high yields and excellent diastereoselectivity (up to 99% yield, >95:5 dr). An investigation of the reaction pathway revealed that the existence and position of the hydroxyl group of styrene played crucial roles in the cascade reaction, suggesting that the two reactants were simultaneously activated by binaphthyl-derived phosphoric acid via hydrogen bonding interactions and long-distance conjugative effects. In addition, the activating group of the hydroxyl functionality in the products can be easily removed or transformed, demonstrating the applicability and utility of this strategy in styrene oxyarylation and in the synthesis of styrene-based compounds.