(1R,2S)-2-(2-aminophenylamino)-1-phenylpropan-1-ol | 1449420-98-7

• 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: (1R,2S)-2-(2-aminophenylamino)-1-phenylpropan-1-ol
• 英文别名: (1R,2S)-2-(2-aminoanilino)-1-phenylpropan-1-ol
• CAS: 1449420-98-7
• 化学式: C₁₅H₁₈N₂O
• 分子量: 242.321
• InChiKey: ARDUJDNEHZLERX-NHYWBVRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  58.3
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-碘苯胺 、 去甲麻黄碱 在 copper(l) iodide 、 吲哚-2-羧酸 、 caesium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 14.0h， 以79%的产率得到(1R,2S)-2-(2-aminophenylamino)-1-phenylpropan-1-ol
  参考文献：
  名称：

  RETRACTED: A room temperature copper catalyzed N-selective arylation of β-amino alcohols with iodoanilines and aryl iodides

  摘要：

  An efficient method is described for the synthesis of N-(2-aminophenyl)-2-hydroxyethylamines via a copper catalyzed N-selective arylation of beta-amino alcohols with iodoanilines. The corresponding coupling products are useful intermediates for the synthesis of a variety of N-2-hydroxyethyl-substituted benzimidazoles, benzimidazolones, and iminobenzimidazoles. We found that 2-iodoaniline only arylates certain amino alcohols but not amines lacking a hydroxyl group. We also demonstrate the arylation of sterically demanding beta-amino alcohols, such as ephedrine and prolinol with aryl iodides at room temperature. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.128

文献信息

• RETRACTED: A room temperature copper catalyzed N-selective arylation of β-amino alcohols with iodoanilines and aryl iodides
  作者：Priyabrata Das、Jef K. De Brabander

  DOI：10.1016/j.tet.2013.04.128

  日期：2013.9

  An efficient method is described for the synthesis of N-(2-aminophenyl)-2-hydroxyethylamines via a copper catalyzed N-selective arylation of beta-amino alcohols with iodoanilines. The corresponding coupling products are useful intermediates for the synthesis of a variety of N-2-hydroxyethyl-substituted benzimidazoles, benzimidazolones, and iminobenzimidazoles. We found that 2-iodoaniline only arylates certain amino alcohols but not amines lacking a hydroxyl group. We also demonstrate the arylation of sterically demanding beta-amino alcohols, such as ephedrine and prolinol with aryl iodides at room temperature. (C) 2013 Elsevier Ltd. All rights reserved.