(1'S,1'S,2S)-N',N'-bis-(1'-phenylethyl)-N-phthaloylphenylalanilamide | 284662-19-7

• 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: (1'S,1'S,2S)-N',N'-bis-(1'-phenylethyl)-N-phthaloylphenylalanilamide
• 英文别名: (2S)-2-(1,3-dioxoisoindol-2-yl)-3-phenyl-N,N-bis[(1S)-1-phenylethyl]propanamide
• CAS: 284662-19-7
• 化学式: C₃₃H₃₀N₂O₃
• 分子量: 502.613
• InChiKey: AIIXOKAOIALCET-JYUFKMNQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  57.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1'S,1'S,2S)-N',N'-bis-(1'-phenylethyl)-N-phthaloylphenylalanilamide 在 肼 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以72.2%的产率得到(1'S,1'S,2S)-N',N'-bis-(1'-phenylethyl)phenylalanilamide
  参考文献：
  名称：

  Stereoselective alkylation of C2-symmetric chiral N-phthaloylglycinamides in the preparation of enantiopure α-amino acids

  摘要：

  The novel, chiral glycinamides (S,S)-3 and (S,S)-4 were prepared in good yields from C-2-symmetric chiral amines (S,S)-1 and (S,S)-2, respectively. Enolate formation and addition to methyl iodide and benzyl bromide proceeded in good yield and high diastereoselectivity, especially in the presence of LiCl or DMPU. Removal of the phthaloyl protecting group with hydrazine, followed by hydrolysis with 6N HCl, converted the benzylated product (S,S,S)-7 to enantiopure (S)-phenylalanine. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00066-5
• 作为产物：
  描述：

  双((S)-1-苯乙基)胺 在 N,N-二甲基丙烯基脲 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 11.0h， 生成 (1'S,1'S,2S)-N',N'-bis-(1'-phenylethyl)-N-phthaloylphenylalanilamide
  参考文献：
  名称：

  Stereoselective alkylation of C2-symmetric chiral N-phthaloylglycinamides in the preparation of enantiopure α-amino acids

  摘要：

  The novel, chiral glycinamides (S,S)-3 and (S,S)-4 were prepared in good yields from C-2-symmetric chiral amines (S,S)-1 and (S,S)-2, respectively. Enolate formation and addition to methyl iodide and benzyl bromide proceeded in good yield and high diastereoselectivity, especially in the presence of LiCl or DMPU. Removal of the phthaloyl protecting group with hydrazine, followed by hydrolysis with 6N HCl, converted the benzylated product (S,S,S)-7 to enantiopure (S)-phenylalanine. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00066-5

文献信息

• Stereoselective alkylation of C2-symmetric chiral N-phthaloylglycinamides in the preparation of enantiopure α-amino acids
  作者：Adelfo Reyes、Eusebio Juaristi

  DOI：10.1016/s0957-4166(00)00066-5

  日期：2000.4

  The novel, chiral glycinamides (S,S)-3 and (S,S)-4 were prepared in good yields from C-2-symmetric chiral amines (S,S)-1 and (S,S)-2, respectively. Enolate formation and addition to methyl iodide and benzyl bromide proceeded in good yield and high diastereoselectivity, especially in the presence of LiCl or DMPU. Removal of the phthaloyl protecting group with hydrazine, followed by hydrolysis with 6N HCl, converted the benzylated product (S,S,S)-7 to enantiopure (S)-phenylalanine. (C) 2000 Elsevier Science Ltd. All rights reserved.