2S-(-)-1,1-dimethylethyl 3-aminocarbonyl-4-<<<(4-amino-2,6-dichlorophenyl)amino>carbonyl>methyl>-1-piperazinecarboxylate | 166520-16-7

• 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: 2S-(-)-1,1-dimethylethyl 3-aminocarbonyl-4-<<<(4-amino-2,6-dichlorophenyl)amino>carbonyl>methyl>-1-piperazinecarboxylate
• 英文别名: S-(-)-2-(aminocarbonyl)-N-(4-amino-2,6-dichlorophenyl)-4-(1,1-dimethylethoxycarbonyl)-1-piperazineacetamide；tert-butyl (3S)-4-[2-(4-amino-2,6-dichloroanilino)-2-oxoethyl]-3-carbamoylpiperazine-1-carboxylate
• CAS: 166520-16-7
• 化学式: C₁₈H₂₅Cl₂N₅O₄
• 分子量: 446.334
• InChiKey: USNWMGRWXJPGFW-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  131
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2S-(-)-1,1-dimethylethyl 3-aminocarbonyl-4-<<<(4-amino-2,6-dichlorophenyl)amino>carbonyl>methyl>-1-piperazinecarboxylate 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以90%的产率得到2S-(-)-2-aminocarbonyl-N-(4-amino-2,6-dichlorophenyl)-1-piperazineacetamide trihydrochloride
  参考文献：
  名称：

  Kinetic Resolution of Piperazine-2-Carboxamide by Leucine Aminopeptidase. An Application in the Synthesis of the Nucleoside Transport Blocker (-) Draflazine

  摘要：

  The resolution of N-t-Boc-piperazine carboxamide 5 proceeded smoothly in the presence of leucine aminopeptidase to produce acid (S)-1 and amide (R)-5 with good optical purity. Sequential alkylation and functional group manipulation of carboxamide (S)-5 provided the known nucleoside transport blocker draflazine (-) 2.

  DOI：

  10.1080/00397919508011814
• 作为产物：
  描述：

  4-BOC-2-哌嗪羧胺 在 platinum on activated charcoal 噻吩 、 Tris buffer pH 8.2 、 氢气 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 25.0~50.0 ℃ 、344.73 kPa 条件下， 反应 172.5h， 生成 2S-(-)-1,1-dimethylethyl 3-aminocarbonyl-4-<<<(4-amino-2,6-dichlorophenyl)amino>carbonyl>methyl>-1-piperazinecarboxylate
  参考文献：
  名称：

  Kinetic Resolution of Piperazine-2-Carboxamide by Leucine Aminopeptidase. An Application in the Synthesis of the Nucleoside Transport Blocker (-) Draflazine

  摘要：

  The resolution of N-t-Boc-piperazine carboxamide 5 proceeded smoothly in the presence of leucine aminopeptidase to produce acid (S)-1 and amide (R)-5 with good optical purity. Sequential alkylation and functional group manipulation of carboxamide (S)-5 provided the known nucleoside transport blocker draflazine (-) 2.

  DOI：

  10.1080/00397919508011814

文献信息

• Kinetic Resolution of Piperazine-2-Carboxamide by Leucine Aminopeptidase. An Application in the Synthesis of the Nucleoside Transport Blocker (-) Draflazine
  作者：M. A. Bruce、D. R. St. Laurent、G. S. Poindexter、I. Monkovic、S. Huang、N. Balasubramanian

  DOI：10.1080/00397919508011814

  日期：1995.9

  The resolution of N-t-Boc-piperazine carboxamide 5 proceeded smoothly in the presence of leucine aminopeptidase to produce acid (S)-1 and amide (R)-5 with good optical purity. Sequential alkylation and functional group manipulation of carboxamide (S)-5 provided the known nucleoside transport blocker draflazine (-) 2.