(S)-2-amino-N-((1S,2S)-2-hydroxy-1,2-diphenylethyl)-N,2-dimethyl-3-phenylpropanamide | 1443008-10-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (S)-2-amino-N-((1S,2S)-2-hydroxy-1,2-diphenylethyl)-N,2-dimethyl-3-phenylpropanamide
• 英文别名: (2S)-2-amino-N-[(1S,2S)-2-hydroxy-1,2-diphenylethyl]-N,2-dimethyl-3-phenylpropanamide
• CAS: 1443008-10-3
• 化学式: C₂₅H₂₈N₂O₂
• 分子量: 388.51
• InChiKey: SYMQWTCZMUPWNA-LSQMVHIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  66.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-amino-N-((1S,2S)-2-hydroxy-1,2-diphenylethyl)-N,2-dimethyl-3-phenylpropanamide 在 水 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 tert-butyl ((R)-1-(((1S,2S)-2-hydroxy-1,2-diphenylethyl)(methyl)amino)-1-oxopropan-2-yl)carbamate
  参考文献：
  名称：

  Synthesis of Quaternary α-Methyl α-Amino Acids by Asymmetric Alkylation of Pseudoephenamine Alaninamide Pivaldimine

  摘要：

  The utility of pseudoephenamine as a chiral auxiliary for the alkylative construction of quaternary alpha-methyl alpha-amino acids Is demonstrated. The method is notable for the high diastereoselectivities of the alkylation reactions, for its versatility with respect to electrophilic substrate partners, and for its mild hydrolysis conditions, which provide alpha-amino acids without salt contaminants. Alternatively, alpha-amino esters can be obtained by direct alcoholysis.

  DOI：

  10.1021/ol401337p
• 作为产物：
  描述：

  lithium benzyloxide 在 盐酸 、 三乙胺 、 lithium chloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 、 苯 为溶剂， -78.0~23.0 ℃ 、26.66 kPa 条件下， 反应 24.37h， 生成 (S)-2-amino-N-((1S,2S)-2-hydroxy-1,2-diphenylethyl)-N,2-dimethyl-3-phenylpropanamide
  参考文献：
  名称：

  Synthesis of Quaternary α-Methyl α-Amino Acids by Asymmetric Alkylation of Pseudoephenamine Alaninamide Pivaldimine

  摘要：

  The utility of pseudoephenamine as a chiral auxiliary for the alkylative construction of quaternary alpha-methyl alpha-amino acids Is demonstrated. The method is notable for the high diastereoselectivities of the alkylation reactions, for its versatility with respect to electrophilic substrate partners, and for its mild hydrolysis conditions, which provide alpha-amino acids without salt contaminants. Alternatively, alpha-amino esters can be obtained by direct alcoholysis.

  DOI：

  10.1021/ol401337p

文献信息

• Synthesis of Quaternary α-Methyl α-Amino Acids by Asymmetric Alkylation of Pseudoephenamine Alaninamide Pivaldimine
  作者：Cedric L. Hugelshofer、Kevin T. Mellem、Andrew G. Myers

  DOI：10.1021/ol401337p

  日期：2013.6.21

  The utility of pseudoephenamine as a chiral auxiliary for the alkylative construction of quaternary alpha-methyl alpha-amino acids Is demonstrated. The method is notable for the high diastereoselectivities of the alkylation reactions, for its versatility with respect to electrophilic substrate partners, and for its mild hydrolysis conditions, which provide alpha-amino acids without salt contaminants. Alternatively, alpha-amino esters can be obtained by direct alcoholysis.