(2R,4R)-4-hydroxy-N-[(1S,2S)-1-hydroxy-1-phenylpropan-2-yl]-N,2-dimethylpentanamide | 176198-66-6

• 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,4R)-4-hydroxy-N-[(1S,2S)-1-hydroxy-1-phenylpropan-2-yl]-N,2-dimethylpentanamide
• CAS: 176198-66-6
• 化学式: C₁₆H₂₅NO₃
• 分子量: 279.379
• InChiKey: PQPNGFAORPWXNS-GUIRCDHDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  60.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (2R,4R)-4-hydroxy-N-[(1S,2S)-1-hydroxy-1-phenylpropan-2-yl]-N,2-dimethylpentanamide 在 4-二甲氨基吡啶 作用下， 生成 [(2R,4R)-5-[[(1S,2S)-1-acetyloxy-1-phenylpropan-2-yl]-methylamino]-4-methyl-5-oxopentan-2-yl] acetate
  参考文献：
  名称：

  Practical Syntheses of Enantiomerically Enriched γ-Lactones and γ-Hydroxy Ketones by the Alkylation of Pseudoephedrine Amides with Epoxides and Their Derivatives

  摘要：

  Pseudoephedrine amide enolates are shown to undergo efficient alkylation reactions with epoxides as electrophiles. Reactions with monosubstituted epoxides are subject to stereochemical matching such that the pairing leading to the 1,3-syn diastereomer is a highly selective, synthetically useful process, while the pairing forming the 1,3-anti diastereomer is not. Reactions with the 1,1-disubstituted epoxide isobutylene oxide are also highly diastereoselective and synthetically useful, but ethylene oxide exhibits poor diastereoselectivity. As an alternative to the use of ethylene oxide, 2-(tert-butyldimethylsilyloxy)ethyl iodide is shown to undergo highly diastereoselective and efficient alkylation reactions with pseudoephedrine amide enolates. Interestingly, epoxides and alkyl halides are found to attack opposite pi-faces of pseudoephedrine amide enolates. The products of each of these alkylation reactions are transformed efficiently into gamma-lactones by acidic hydrolysis and into methyl ketones by the addition of methyllithium. The methodology described provides useful procedures for the synthesis of enantiomerically enriched gamma-lactones and gamma-hydroxy ketones.

  DOI：

  10.1021/jo952032o
• 作为产物：
  描述：

  (1S,2S)-(+)-伪麻黄碱丙酰胺 在 四丁基氟化铵 、 lithium chloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 14.25h， 生成 (2R,4R)-4-hydroxy-N-[(1S,2S)-1-hydroxy-1-phenylpropan-2-yl]-N,2-dimethylpentanamide
  参考文献：
  名称：

  Practical Syntheses of Enantiomerically Enriched γ-Lactones and γ-Hydroxy Ketones by the Alkylation of Pseudoephedrine Amides with Epoxides and Their Derivatives

  摘要：

  Pseudoephedrine amide enolates are shown to undergo efficient alkylation reactions with epoxides as electrophiles. Reactions with monosubstituted epoxides are subject to stereochemical matching such that the pairing leading to the 1,3-syn diastereomer is a highly selective, synthetically useful process, while the pairing forming the 1,3-anti diastereomer is not. Reactions with the 1,1-disubstituted epoxide isobutylene oxide are also highly diastereoselective and synthetically useful, but ethylene oxide exhibits poor diastereoselectivity. As an alternative to the use of ethylene oxide, 2-(tert-butyldimethylsilyloxy)ethyl iodide is shown to undergo highly diastereoselective and efficient alkylation reactions with pseudoephedrine amide enolates. Interestingly, epoxides and alkyl halides are found to attack opposite pi-faces of pseudoephedrine amide enolates. The products of each of these alkylation reactions are transformed efficiently into gamma-lactones by acidic hydrolysis and into methyl ketones by the addition of methyllithium. The methodology described provides useful procedures for the synthesis of enantiomerically enriched gamma-lactones and gamma-hydroxy ketones.

  DOI：

  10.1021/jo952032o