(2R)-2-dimethoxyphosphoryl-2-methyl-3-phenyl-N-[(1S)-1-phenylethyl]propanamide | 850425-48-8

• 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: (2R)-2-dimethoxyphosphoryl-2-methyl-3-phenyl-N-[(1S)-1-phenylethyl]propanamide
• CAS: 850425-48-8
• 化学式: C₂₀H₂₆NO₄P
• 分子量: 375.404
• InChiKey: LJPJUTZCTDKKKL-OXJNMPFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  [1-((S)-1-Phenyl-ethylcarbamoyl)-ethyl]-phosphonic acid dimethyl ester 、 溴甲苯 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (2R)-2-dimethoxyphosphoryl-2-methyl-3-phenyl-N-[(1S)-1-phenylethyl]propanamide 、 (2S)-2-dimethoxyphosphoryl-2-methyl-3-phenyl-N-[(1S)-1-phenylethyl]propanamide
  参考文献：
  名称：

  Asymmetric alkylation of dimethoxyphosphoryl-N-[1-(S)-α-methylbenzyl]acetamide enolates. Synthesis of both stereoisomers from the same source of chirality by changing the equivalents of LDA

  摘要：

  已经开发出一种新方法，可以从单一的手性来源合成两种立体异构体。

  DOI：

  10.1039/b416616g

文献信息

• Asymmetric alkylation of dimethoxyphosphoryl-N-[1-(S)-α-methylbenzyl]acetamide enolates. Synthesis of both stereoisomers from the same source of chirality by changing the equivalents of LDA
  作者：Mario Ordóñez、Eugenio Hernández-Fernández、Janet Xahuentitla、Carlos Cativiela

  DOI：10.1039/b416616g

  日期：——

  A new methodology has been developed for the synthesis of both stereoisomers from a single chiral source.

  已经开发出一种新方法，可以从单一的手性来源合成两种立体异构体。
• Reversal of diastereoselectivity in the benzylation of the lithium enolates of phosphonopropanoamides by changing the base equivalents
  作者：Mario Ordóñez、Eugenio Hernández-Fernández、Haydée Rojas-Cabrera、Victoria Labastida-Galván

  DOI：10.1016/j.tetasy.2008.11.028

  日期：2008.12

  Phosphonopropanoamides bearing (S)-alpha-methylbenzylamine were easily obtained, and the benzylation of their enolates examined. Surprisingly, a reversal of the pi-facial diastereoselectivity was observed by changing the number of equivalents of the lithium base. Reaction of the lithium enolate obtained using 2.0 equiv of LDA, LiHMDS or LTMP with benzyl bromide afforded the (R,S)-diastereoisomer, whereas the use of >= 2.5 equiv of lithium base gave the (S,S)-diastereoisomer. In contrast, a reversal of diastereoselectivity was not observed with sodium or potassium bases. This reversal is attributed to the formation of aggregates of the enolates. The results presented here provide valuable guidelines to tune the selective preparation of enantiopure compounds from the same source of chirality. (C) 2009 Elsevier Ltd. All rights reserved.
• Reversal Diastereoselectivity in the Benzylation of Phosphonopropanoamides
  作者：Javier Cervantes-González、Selene Lagunas-Rivera、Mario Ordóñez

  DOI：10.1080/10426507.2010.522638

  日期：2011.3.31

  A convenient and efficient preparation of phosphonopropanoamides bearing (S)-1-(1'-naphthyl) ethylamine, (S)-3,3-dimethyl-2-butylamine, and (S)-2-amine-3-methylbutane in good yield has been achieved. The stereochemical outcome of the asymmetric benzylation reaction of their enolates changes dramatically with the LDA equivalents used. The enolization of the phosphopropanoamides with LDA (2 equiv.) followed by the reaction with benzyl bromide gives rise to the (R,S) quaternary phosphonoamides, whereas the (S,S) diastereoisomer can be obtained by enolization with LDA (>= 2.5 equiv.) followed by the addition of benzyl bromide. This method provides access to both diastereoisomers changing only the base equivalents.