(S)-N-tert-Butyl-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-oxo-3-phenyl-propionamide | 160648-63-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-N-tert-Butyl-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-oxo-3-phenyl-propionamide
• CAS: 160648-63-5
• 化学式: C₂₁H₂₀N₂O₄
• 分子量: 364.401
• InChiKey: HINKYCLKGVCVKB-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.45
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  83.55
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S)-N-tert-Butyl-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-oxo-3-phenyl-propionamide 在 盐酸 、 sodium tetrahydroborate 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 0.17h， 生成 3-苯基-L-丝氨酸
  参考文献：
  名称：

  Stereocontrolled synthesis of β-hydroxyphenylalanine and β-hydroxytyrosine derivatives

  摘要：

  Side-chain bromination of N-phthaloyl-(S)-phenylalanine and tyrosine derivatives, followed by treatment of the product bromides with silver nitrate in aqueous acetone, affords the corresponding (2S,3R)-beta-hydroxy-alpha-amino acids, enantiospecifically and diastereoselectively. The diastereoselectivity depends on the carboxyl protecting group, tert-Butyl esters display greater stereoselectivity than the corresponding methyl esters, presumably as a result of a steric effect, while N-tert-butylamides react diastereospecifically due to a combination of steric and electronic effects.

  DOI：

  10.1016/s0040-4020(01)85256-x
• 作为产物：
  描述：

  (2S,3R)-3-hydroxy-N-tert-butyl-N²-phthaloylphenylalanylamide 在 jones reagent 作用下， 以 丙酮 为溶剂， 反应 0.25h， 以67%的产率得到(S)-N-tert-Butyl-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-oxo-3-phenyl-propionamide
  参考文献：
  名称：

  Stereocontrolled synthesis of β-hydroxyphenylalanine and β-hydroxytyrosine derivatives

  摘要：

  Side-chain bromination of N-phthaloyl-(S)-phenylalanine and tyrosine derivatives, followed by treatment of the product bromides with silver nitrate in aqueous acetone, affords the corresponding (2S,3R)-beta-hydroxy-alpha-amino acids, enantiospecifically and diastereoselectively. The diastereoselectivity depends on the carboxyl protecting group, tert-Butyl esters display greater stereoselectivity than the corresponding methyl esters, presumably as a result of a steric effect, while N-tert-butylamides react diastereospecifically due to a combination of steric and electronic effects.

  DOI：

  10.1016/s0040-4020(01)85256-x