N-benzoyl-L-β-tert-butylalanine | 459836-81-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-benzoyl-L-β-tert-butylalanine
• 英文别名: (2S)-2-benzamido-4,4-dimethylpentanoic acid
• CAS: 459836-81-8
• 化学式: C₁₄H₁₉NO₃
• 分子量: 249.31
• InChiKey: SAXFLDAJFZSACF-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-benzoyl-L-β-tert-butylalanine 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以94%的产率得到4-neopentyl-2-phenyloxazol-5(4H)-one
  参考文献：
  名称：

  Peptide-Catalyzed Conversion of Racemic Oxazol-5(4H)-ones into Enantiomerically Enriched α-Amino Acid Derivatives

  摘要：

  We report the development and optimization of a tetrapeptide that catalyzes the methanolytic dynamic kinetic resolution of oxazol-5(4H)-ones (azlactones) with high levels of enantioinduction. Oxazolones possessing benzylic-type substituents were found to perform better than others, providing methyl ester products in 88:12 to 98:2 er. The mechanism of this peptide-catalyzed process was investigated through truncation studies and competition experiments. High-field NOESY analysis was performed to elucidate the solution-phase structure of the peptide, and we present a plausible model for catalysis.

  DOI：

  10.1021/jo402828f
• 作为产物：
  描述：

  L-α-新戊基甘氨酸 、 苯甲酰氯 在 sodium hydroxide 作用下， 以 水 为溶剂， 以63%的产率得到N-benzoyl-L-β-tert-butylalanine
  参考文献：
  名称：

  Peptide-Catalyzed Conversion of Racemic Oxazol-5(4H)-ones into Enantiomerically Enriched α-Amino Acid Derivatives

  摘要：

  We report the development and optimization of a tetrapeptide that catalyzes the methanolytic dynamic kinetic resolution of oxazol-5(4H)-ones (azlactones) with high levels of enantioinduction. Oxazolones possessing benzylic-type substituents were found to perform better than others, providing methyl ester products in 88:12 to 98:2 er. The mechanism of this peptide-catalyzed process was investigated through truncation studies and competition experiments. High-field NOESY analysis was performed to elucidate the solution-phase structure of the peptide, and we present a plausible model for catalysis.

  DOI：

  10.1021/jo402828f

文献信息

• Pd-Catalyzed Enantioselective C–H Iodination: Asymmetric Synthesis of Chiral Diarylmethylamines
  作者：Ling Chu、Xiao-Chen Wang、Curtis E. Moore、Arnold L. Rheingold、Jin-Quan Yu

  DOI：10.1021/ja408864c

  日期：2013.11.6

  An enantioselective C-H iodination reaction using a mono-N-benzoyl-protected amino acid has been developed for the synthesis of chiral diarylmethylamines. The reaction uses iodine as the sole oxidant and proceeds at ambient temperature and under air.
• Peptide-Catalyzed Conversion of Racemic Oxazol-5(4<i>H</i>)-ones into Enantiomerically Enriched α-Amino Acid Derivatives
  作者：Anthony J. Metrano、Scott J. Miller

  DOI：10.1021/jo402828f

  日期：2014.2.21

  We report the development and optimization of a tetrapeptide that catalyzes the methanolytic dynamic kinetic resolution of oxazol-5(4H)-ones (azlactones) with high levels of enantioinduction. Oxazolones possessing benzylic-type substituents were found to perform better than others, providing methyl ester products in 88:12 to 98:2 er. The mechanism of this peptide-catalyzed process was investigated through truncation studies and competition experiments. High-field NOESY analysis was performed to elucidate the solution-phase structure of the peptide, and we present a plausible model for catalysis.