[2-(3,4-Dimethoxy-phenyl)-eth-(E)-ylidene]-(4-methoxy-phenyl)-amine | 399042-99-0

• 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-(3,4-Dimethoxy-phenyl)-eth-(E)-ylidene]-(4-methoxy-phenyl)-amine
• 英文别名: 2-(3,4-dimethoxyphenyl)-N-(4-methoxyphenyl)ethanimine
• CAS: 399042-99-0
• 化学式: C₁₇H₁₉NO₃
• 分子量: 285.343
• InChiKey: DATYJZUUHXEHAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  40
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲基锂 、 [2-(3,4-Dimethoxy-phenyl)-eth-(E)-ylidene]-(4-methoxy-phenyl)-amine 在 鹰爪豆碱 作用下， 以 乙醚 为溶剂， 反应 2.0h， 生成 (S)-N-[2-(3,4-dimethoxyphenylpropyl)]-4-methoxyaniline 、 (-)-(R)-N-[2-(3,4-dimethoxyphenyl)-1-methylethyl]-N-(4-methoxyphenyl)amine
  参考文献：
  名称：

  Synthesis of enantiomerically enriched amines by chiral ligand mediated addition of organolithium reagents to imines

  摘要：

  The effect of the imine and ligand structure on the enantioselective addition or organolithiums to imines has been studied. Thus, (-)-sparteine-mediated additions or MeLi and or n-BuLi to p-anisidine derived phenylimine 1a afforded the corresponding amines with modest e.e.s. The use of bulkier or more reactive imines (naphthyl or toss I imines) resulted ill loss Of enantioselectivity. The best enantioinduction with this ligand,Nas obtained with enolizable imines 8 and 10. When bis(oxazolidines) were used as chiral ligands, a strong influence of their structure in the enantioselectivity or the addition of MeLi and n-BuLi to phenylimine 1a was observed. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00344-5
• 作为产物：
  描述：

  (3,4-二甲氧基苯基)乙醛 、 甲氧苯胺 在 sodium sulfate 作用下， 生成 [2-(3,4-Dimethoxy-phenyl)-eth-(E)-ylidene]-(4-methoxy-phenyl)-amine
  参考文献：
  名称：

  Synthesis of enantiomerically enriched amines by chiral ligand mediated addition of organolithium reagents to imines

  摘要：

  The effect of the imine and ligand structure on the enantioselective addition or organolithiums to imines has been studied. Thus, (-)-sparteine-mediated additions or MeLi and or n-BuLi to p-anisidine derived phenylimine 1a afforded the corresponding amines with modest e.e.s. The use of bulkier or more reactive imines (naphthyl or toss I imines) resulted ill loss Of enantioselectivity. The best enantioinduction with this ligand,Nas obtained with enolizable imines 8 and 10. When bis(oxazolidines) were used as chiral ligands, a strong influence of their structure in the enantioselectivity or the addition of MeLi and n-BuLi to phenylimine 1a was observed. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00344-5