2-Amino-3-(methoxycarbonyl)-2'-(N-phenylamino)-1,1'-binaphthyl

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-Amino-3-(methoxycarbonyl)-2'-(N-phenylamino)-1,1'-binaphthyl
• 英文别名: Methyl 3-amino-4-(2-anilinonaphthalen-1-yl)naphthalene-2-carboxylate
• 化学式: C₂₈H₂₂N₂O₂
• 分子量: 418.495
• InChiKey: HAGIQYLJYTWVBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  64.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-苯基-2-萘胺 、 甲基3-氨基-2-萘甲酸酯 在 叔丁胺 作用下， 以 甲醇 为溶剂， 反应 72.0h， 以20%的产率得到3,3’-bis(methoxycarbonyl)-2,2’-diamino-1,1’-binaphthyle
  参考文献：
  名称：

  Selective Cross-Coupling of 2-Naphthol and 2-Naphthylamine Derivatives. A Facile Synthesis of 2,2',3-Trisubstituted and 2,2',3,3'-Tetrasubstituted 1,1'-Binaphthyls

  摘要：

  The novel 1,1'-binaphthyls with OH and/or NHR (R=H or Ph) groups in the 2,2'-positions and with additional methoxycarbonyl group(s) in the 3- or 3,3'-positions (13-18) have been synthesized from their respective precursors 1-5 by the CuCl2/t-BuNH(2)-mediated oxidative cross-coupling. In most cases, the chemoselectivity was good, and the cross-coupled products 11-18 were obtained in fair to excellent yields. Binaphthyls 6-10, resulting from the self-coupling, and carbazoles 19-23 have been identified as byproducts. Ab initio calculations and electrochemical measurements have been employed to account for the observed selectivity.

  DOI：

  10.1021/jo00087a036