(S)-2-(2,6-dichlorobenzylamino)-3-phenylpropan-1-ol | 1374996-08-3

• 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: (S)-2-(2,6-dichlorobenzylamino)-3-phenylpropan-1-ol
• 英文别名: (2S)-2-[(2,6-dichlorophenyl)methylamino]-3-phenylpropan-1-ol
• CAS: 1374996-08-3
• 化学式: C₁₆H₁₇Cl₂NO
• 分子量: 310.223
• InChiKey: ZULZDOXXULJAGF-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  L-苯丙氨醇 、 2,6-二氯苄基溴 在 tetraethylammonium hexafluorophosphate 、 乙腈 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以70%的产率得到(S)-2-(2,6-dichlorobenzylamino)-3-phenylpropan-1-ol
  参考文献：
  名称：

  Electrogenerated acetonitrile anion induced selective N-alkylation of bifunctional compounds

  摘要：

  The simple galvanostatic reduction of a solution of MeCN-0.1 M Et4NPF6 leads to the formation of acetonitrile anion, whose counter-ion is the Et4N+ cation, which leaves the anion 'naked'. This enhances the reactivity of acetonitrile anion, which reveals to be selective in the N-monoalkylation of bifunctional compounds (cycloserine, beta-amino alcohols, 2-substituted anilines) obtaining high yields. N,N-bis-alkylation has never been observed, indicating that the electrochemical methodology is highly regioselective. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.03.038

文献信息

• Electrogenerated acetonitrile anion induced selective N-alkylation of bifunctional compounds
  作者：Marta Feroci、Daniela De Vita、Luigi Scipione、Giovanni Sotgiu、Silvano Tortorella

  DOI：10.1016/j.tetlet.2012.03.038

  日期：2012.5

  The simple galvanostatic reduction of a solution of MeCN-0.1 M Et4NPF6 leads to the formation of acetonitrile anion, whose counter-ion is the Et4N+ cation, which leaves the anion 'naked'. This enhances the reactivity of acetonitrile anion, which reveals to be selective in the N-monoalkylation of bifunctional compounds (cycloserine, beta-amino alcohols, 2-substituted anilines) obtaining high yields. N,N-bis-alkylation has never been observed, indicating that the electrochemical methodology is highly regioselective. (C) 2012 Elsevier Ltd. All rights reserved.