(R)-(-)-1-[(2-methoxy-5-methyl)phenyl]-2-phenylethylamine | 859846-07-4

• 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: (R)-(-)-1-[(2-methoxy-5-methyl)phenyl]-2-phenylethylamine
• 英文别名: (R)-(-)-1-(2-methoxy-5-methyl)-2-phenylethylamine
• CAS: 859846-07-4
• 化学式: C₁₆H₁₉NO
• 分子量: 241.333
• InChiKey: QBDIZEAFCPIQNU-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.25
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  35.25
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (R)-(-)-1-[(2-methoxy-5-methyl)phenyl]-2-phenylethylamine 在 aluminum tri-bromide 、 硫酸 、 尿素 作用下， 以 甲苯 为溶剂， 反应 122.0h， 生成 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：

  1-(2-methoxy-5-methyl)-2-phenylethylamine 在 sodium hydroxide 、 D-酒石酸 作用下， 以 乙醇 为溶剂， 以25%的产率得到(R)-(-)-1-[(2-methoxy-5-methyl)phenyl]-2-phenylethylamine
  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

文献信息

• <i>N</i>-[(<i>R</i>)-1-(2-Hydroxy-5-methylphenyl)ethyl]-<i>N</i>-[(<i>R</i>)-1-(2-methoxy-5-methylphenyl)-2-phenylethyl]aminium chloride
  作者：Xiao-Feng Yang、Guang-You Zhang、Yan Zhang、Jin-Yan Zhao、Xiang-Bo Wang

  DOI：10.1107/s0108270105005676

  日期：2005.4.15

  The title compound, C(25)H(30)NO(2)(+)center dot Cl-, has been synthesized, and the crystal structure shows that it is mainly stabilized through intermolecular N-H center dot center dot center dot Cl and O-H center dot center dot center dot Cl and intramolecular N-H center dot center dot center dot O hydrogen bonds. The absolute configuration of the new stereogenic center (the C atom adjacent to the N atom on the phenol side) was determined to have an R configuration.