N-[diethoxyphosphoryl(phenyl)methyl]-2-methylpropan-1-amine | 1352964-91-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: N-[diethoxyphosphoryl(phenyl)methyl]-2-methylpropan-1-amine
• CAS: 1352964-91-0
• 化学式: C₁₅H₂₆NO₃P
• 分子量: 299.35
• InChiKey: UESMFRLKLNGGGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  二乙氧基磷酰-苯基-甲醇 、 异丁胺 反应 0.67h， 以54%的产率得到N-[diethoxyphosphoryl(phenyl)methyl]-2-methylpropan-1-amine
  参考文献：
  名称：

  A neighbouring group effect leading to enhanced nucleophilic substitution of amines at the hindered α-carbon atom of an α-hydroxyphosphonate

  摘要：

  Diethyl alpha-hydroxy-benzylphosphonate undergoes nucleophilic substitution with primary amines of sufficient reactivity at around 100 degrees C to afford the corresponding alpha-aminophosphonates. The substitution can be enhanced by microwave irradiation. The reaction takes place with surprising ease due to the neighbouring group effect of the P=O moiety as was justified by DFT calculations carried out to evaluate the mechanism of the substitution under discussion. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.11.026

文献信息

• A neighbouring group effect leading to enhanced nucleophilic substitution of amines at the hindered α-carbon atom of an α-hydroxyphosphonate
  作者：Nóra Zsuzsa Kiss、Anna Kaszás、László Drahos、Zoltán Mucsi、György Keglevich

  DOI：10.1016/j.tetlet.2011.11.026

  日期：2012.1

  Diethyl alpha-hydroxy-benzylphosphonate undergoes nucleophilic substitution with primary amines of sufficient reactivity at around 100 degrees C to afford the corresponding alpha-aminophosphonates. The substitution can be enhanced by microwave irradiation. The reaction takes place with surprising ease due to the neighbouring group effect of the P=O moiety as was justified by DFT calculations carried out to evaluate the mechanism of the substitution under discussion. (C) 2011 Elsevier Ltd. All rights reserved.