dimethyl (1R,2S)-2-(N,N-dibenzylamino)-1-mesyloxy-3-phenylpropylphosphonate | 1166857-21-1

• 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: dimethyl (1R,2S)-2-(N,N-dibenzylamino)-1-mesyloxy-3-phenylpropylphosphonate
• 英文别名: [(1R,2S)-2-(dibenzylamino)-1-[dimethoxy(oxido)phosphaniumyl]-3-phenylpropyl] methanesulfonate
• CAS: 1166857-21-1
• 化学式: C₂₆H₃₂NO₆PS
• 分子量: 517.583
• InChiKey: JNSZURZBSXRXQC-IZZNHLLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  35
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  96.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  dimethyl (1R,2S)-2-(N,N-dibenzylamino)-1-hydroxy-3-phenylpropylphosphonate 、 甲基磺酸酐 在 三乙胺 作用下， 以 氘代氯仿 为溶剂， 反应 1.75h， 生成 dimethyl (1R,2S)-2-(N,N-dibenzylamino)-1-mesyloxy-3-phenylpropylphosphonate 、 dimethyl (1S,2R)-1-(N,N-dibenzylamino)-2-mesyloxy-3-phenylpropylphosphonate 、 (2S,3S)-1,1,2-tribenzyl-3-(dimethoxyphosphoryl)aziridinium mesylate
  参考文献：
  名称：

  Direct observation of aziridinium ions in a 2-(N,N-dibenzylamino)- to 1-(N,N-dibenzylamino)phosphonate rearrangement

  摘要：

  Aziridinium mesylates stable in the reaction medium for several hours to over a week were observed in a rearrangement of dimethyl (1R,2S)-2-(N,N-dibenzylamino)-1-mesyloxyethylphosphonates substituted at C2 with Bn, i-Pr and t-Bu to the respective 1-(N,N-dibenzylamino)-2-mesyloxyethylphosphonates. Rates of formation of these aziridinium mesylates and rates of their reactions with poorly nucleophilic mesylate anion were governed by steric and electronic factors. The conformation of (2S,3S)-1,1-dibenzyl-2-(tert-butyl)-3-(dimethoxyphosphoryl)aziridinium mesylate in solution was established based on H-1 and C-13 NMR spectroscopic studies including a NOESY experiment. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.03.087

文献信息

• Direct observation of aziridinium ions in a 2-(N,N-dibenzylamino)- to 1-(N,N-dibenzylamino)phosphonate rearrangement
  作者：Dorota G. Piotrowska、Andrzej E. Wróblewski

  DOI：10.1016/j.tet.2009.03.087

  日期：2009.5

  Aziridinium mesylates stable in the reaction medium for several hours to over a week were observed in a rearrangement of dimethyl (1R,2S)-2-(N,N-dibenzylamino)-1-mesyloxyethylphosphonates substituted at C2 with Bn, i-Pr and t-Bu to the respective 1-(N,N-dibenzylamino)-2-mesyloxyethylphosphonates. Rates of formation of these aziridinium mesylates and rates of their reactions with poorly nucleophilic mesylate anion were governed by steric and electronic factors. The conformation of (2S,3S)-1,1-dibenzyl-2-(tert-butyl)-3-(dimethoxyphosphoryl)aziridinium mesylate in solution was established based on H-1 and C-13 NMR spectroscopic studies including a NOESY experiment. (C) 2009 Elsevier Ltd. All rights reserved.