2-(2-{5-[(tert-butoxycarbonyl)amino]-2-methoxyphenyl}-1-methoxyethyl)phenyl trifluoromethanesulfonate | 1613485-49-6

• 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: 2-(2-{5-[(tert-butoxycarbonyl)amino]-2-methoxyphenyl}-1-methoxyethyl)phenyl trifluoromethanesulfonate
• CAS: 1613485-49-6
• 化学式: C₂₂H₂₆F₃NO₇S
• 分子量: 505.512
• InChiKey: YOJQXBNKZOJUJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  34.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  100.16
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-(2-{5-[(tert-butoxycarbonyl)amino]-2-methoxyphenyl}-1-methoxyethyl)phenyl trifluoromethanesulfonate 在 palladium 10% on activated carbon 、 ammonium acetate 、 magnesium 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以82%的产率得到tert-butyl [4-methoxy-3-(2-methoxy-2-phenylethyl)phenyl]carbamate
  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
• 作为产物：
  描述：

  乙酰苯 在 吡啶 、 S-联萘酚磷酸酯 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 24.0h， 生成 2-(2-{5-[(tert-butoxycarbonyl)amino]-2-methoxyphenyl}-1-methoxyethyl)phenyl trifluoromethanesulfonate
  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