2-((R)-1-amino-2-phenylethyl)-4-methylphenol | 946838-81-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-((R)-1-amino-2-phenylethyl)-4-methylphenol
• CAS: 946838-81-9
• 化学式: C₁₅H₁₇NO
• 分子量: 227.306
• InChiKey: MWBPPOBDWNZREF-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.94
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  46.25
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-((R)-1-amino-2-phenylethyl)-4-methylphenol 、 叔丁醇 在 硫酸 、 尿素 作用下， 反应 72.0h， 以20%的产率得到2-((R)-1-amino-2-phenylethyl)-6-tert-butyl-4-methyl-phenol
  参考文献：
  名称：

  Synthesis of novel chiral 1,3-aminophenols and application for the enantioselective addition of diethylzinc to aldehydes

  摘要：

  Novel chiral 1,3-aminophenols were efficiently synthesized by applying a Friedel-Crafts reaction and optical resolution. The catalytic activity of the aminophenols was studied for the addition of diethylzinc to benzaldehyde. The results showed that (S)-5a with bulky tert-butyl groups on the stereogenic carbon atom and 4,6-positions of phenol favored higher enantio selectivity (94% ee). The same ligand was also used with other aldehydes, to give optically active alcohols in good chemical yields and cc values (up to 99%). (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.05.027
• 作为产物：
  描述：

  (R)-(-)-1-[(2-methoxy-5-methyl)phenyl]-2-phenylethylamine 在 aluminum tri-bromide 作用下， 以 甲苯 为溶剂， 反应 50.0h， 以75%的产率得到2-((R)-1-amino-2-phenylethyl)-4-methylphenol
  参考文献：
  名称：

  Synthesis of novel chiral 1,3-aminophenols and application for the enantioselective addition of diethylzinc to aldehydes

  摘要：

  Novel chiral 1,3-aminophenols were efficiently synthesized by applying a Friedel-Crafts reaction and optical resolution. The catalytic activity of the aminophenols was studied for the addition of diethylzinc to benzaldehyde. The results showed that (S)-5a with bulky tert-butyl groups on the stereogenic carbon atom and 4,6-positions of phenol favored higher enantio selectivity (94% ee). The same ligand was also used with other aldehydes, to give optically active alcohols in good chemical yields and cc values (up to 99%). (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.05.027