1-tert-butoxycarbonyl-4-phenoxycarbonyl-1,4,5,6-tetrahydropyrazine-2-(N-tert-butyl)carboxamide | 221557-13-7

• 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-tert-butoxycarbonyl-4-phenoxycarbonyl-1,4,5,6-tetrahydropyrazine-2-(N-tert-butyl)carboxamide
• 英文别名: 4-O-tert-butyl 1-O-phenyl 5-(tert-butylcarbamoyl)-2,3-dihydropyrazine-1,4-dicarboxylate
• CAS: 221557-13-7
• 化学式: C₂₁H₂₉N₃O₅
• 分子量: 403.478
• InChiKey: YKZZKGUSOXDLJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  88.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-tert-butoxycarbonyl-4-phenoxycarbonyl-1,4,5,6-tetrahydropyrazine-2-(N-tert-butyl)carboxamide 在 PF6 、 (S,S)-2,2''-bis<(R)-1-(diisobutylphosphino)ethyl>-1,1''-biferrocene 、 氢气 作用下， 以 1,2-二氯乙烷 为溶剂， 50.0 ℃ 、98.06 kPa 条件下， 反应 24.0h， 以100%的产率得到1-tert-butoxycarbonyl-4-phenoxycarbonylpiperazine-2-(N-tert-butyl)carboxamide
  参考文献：
  名称：

  Asymmetric Hydrogenation of 1,4,5,6-Tetrahydropyrazine-2-(N-tert-butyl)carboxamide Catalyzed by Trans-Chelating Chiral Diphosphine−Rhodium Complexes

  摘要：

  Highly enantioselective hydrogenation of 1,4,5,6-tetrahydropyrazine-2-(N-tert-butyl)carboxamide (2) was accomplished by a rhodium complex coordinated with a chiral diphosphine TRAP ligand, which is possible to chelate to a transition metal atom in a trans-manner. Of particular interest is that (R,R)-(S,S)-i-BuTRAP gave 97% ee of the corresponding piperazine-2-carboxylic acid derivative (3) with (S) configuration, while the hydrogenation with (R,R)-(S,S)-MeTRAP-rhodium catalyst provided (R)-3 with up to 85% ee. P-31 NMR studies of behavior of i-Bu- and MeTRAP-rhodium catalysts during the reaction suggest that the asymmetric hydrogenation of 2 with TRAPs may involve two competitive reaction pathways, giving their respective enantiomeric products 3.

  DOI：

  10.1021/jo981939u
• 作为产物：
  描述：

  氯甲酸苯酯 、 1-tert-butoxycarbonyl-1,4,5,6-tetrahydropyrazine-2-(N-tert-butyl)carboxamide 在 碳酸氢钠 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 反应 1.0h， 以79%的产率得到1-tert-butoxycarbonyl-4-phenoxycarbonyl-1,4,5,6-tetrahydropyrazine-2-(N-tert-butyl)carboxamide
  参考文献：
  名称：

  Asymmetric Hydrogenation of 1,4,5,6-Tetrahydropyrazine-2-(N-tert-butyl)carboxamide Catalyzed by Trans-Chelating Chiral Diphosphine−Rhodium Complexes

  摘要：

  Highly enantioselective hydrogenation of 1,4,5,6-tetrahydropyrazine-2-(N-tert-butyl)carboxamide (2) was accomplished by a rhodium complex coordinated with a chiral diphosphine TRAP ligand, which is possible to chelate to a transition metal atom in a trans-manner. Of particular interest is that (R,R)-(S,S)-i-BuTRAP gave 97% ee of the corresponding piperazine-2-carboxylic acid derivative (3) with (S) configuration, while the hydrogenation with (R,R)-(S,S)-MeTRAP-rhodium catalyst provided (R)-3 with up to 85% ee. P-31 NMR studies of behavior of i-Bu- and MeTRAP-rhodium catalysts during the reaction suggest that the asymmetric hydrogenation of 2 with TRAPs may involve two competitive reaction pathways, giving their respective enantiomeric products 3.

  DOI：

  10.1021/jo981939u

文献信息

• Asymmetric Hydrogenation of 1,4,5,6-Tetrahydropyrazine-2-(<i>N</i>-<i>tert</i>-butyl)carboxamide Catalyzed by Trans-Chelating Chiral Diphosphine−Rhodium Complexes
  作者：Ryoichi Kuwano、Yoshihiko Ito

  DOI：10.1021/jo981939u

  日期：1999.2.1

  Highly enantioselective hydrogenation of 1,4,5,6-tetrahydropyrazine-2-(N-tert-butyl)carboxamide (2) was accomplished by a rhodium complex coordinated with a chiral diphosphine TRAP ligand, which is possible to chelate to a transition metal atom in a trans-manner. Of particular interest is that (R,R)-(S,S)-i-BuTRAP gave 97% ee of the corresponding piperazine-2-carboxylic acid derivative (3) with (S) configuration, while the hydrogenation with (R,R)-(S,S)-MeTRAP-rhodium catalyst provided (R)-3 with up to 85% ee. P-31 NMR studies of behavior of i-Bu- and MeTRAP-rhodium catalysts during the reaction suggest that the asymmetric hydrogenation of 2 with TRAPs may involve two competitive reaction pathways, giving their respective enantiomeric products 3.