4-Acetyl-5,6-dihydro-4H-pyrazine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester | 171504-83-9

• 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: 4-Acetyl-5,6-dihydro-4H-pyrazine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester
• 英文别名: 1-O-tert-butyl 5-O-methyl 4-acetyl-2,3-dihydropyrazine-1,5-dicarboxylate
• CAS: 171504-83-9
• 化学式: C₁₃H₂₀N₂O₅
• 分子量: 284.312
• InChiKey: ROALSHFZNQUTMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  76.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-Acetyl-5,6-dihydro-4H-pyrazine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 生成 1-(tert-butyl) 3-methyl 4-acetylpiperazine-1,3-dicarboxylate
  参考文献：
  名称：

  Asymmetric hydrogenation of tetrahydropyrazines: Synthesis of (S)-piperazine-2-tert-butylcarboxamide, an intermediate in the preparation of the HIV protease inhibitor indinavir

  摘要：

  Hydrogenation of tetrahydropyrazine 4g with [(R)-BINAP(COD)Rh]TfO gave piperazine 6g in 96% yield and 99% ee. Simple hydrogenolytic deprotection and crystallization afforded the key chiral (S)-N-Boc-piperazine MK-639 intermediate 1 in high yield and enantiomeric purity.

  DOI：

  10.1016/0040-4039(95)01345-i
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 methyl 1-acetyl-1,4,5,6-tetrahydropyrazine-2-carboxylate 在 4-二甲氨基吡啶 作用下， 生成 4-Acetyl-5,6-dihydro-4H-pyrazine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester
  参考文献：
  名称：

  Asymmetric hydrogenation of tetrahydropyrazines: Synthesis of (S)-piperazine-2-tert-butylcarboxamide, an intermediate in the preparation of the HIV protease inhibitor indinavir

  摘要：

  Hydrogenation of tetrahydropyrazine 4g with [(R)-BINAP(COD)Rh]TfO gave piperazine 6g in 96% yield and 99% ee. Simple hydrogenolytic deprotection and crystallization afforded the key chiral (S)-N-Boc-piperazine MK-639 intermediate 1 in high yield and enantiomeric purity.

  DOI：

  10.1016/0040-4039(95)01345-i

文献信息

• Asymmetric hydrogenation of tetrahydropyrazines: Synthesis of (S)-piperazine-2-tert-butylcarboxamide, an intermediate in the preparation of the HIV protease inhibitor indinavir
  作者：K. Rossen、Steven A. Weissman、J. Sager、R.A. Reamer、D. Askin、R.P. Volante、P.J. Reider

  DOI：10.1016/0040-4039(95)01345-i

  日期：1995.9

  Hydrogenation of tetrahydropyrazine 4g with [(R)-BINAP(COD)Rh]TfO gave piperazine 6g in 96% yield and 99% ee. Simple hydrogenolytic deprotection and crystallization afforded the key chiral (S)-N-Boc-piperazine MK-639 intermediate 1 in high yield and enantiomeric purity.
• A New Planar Chiral Bisphosphine Ligand for Asymmetric Catalysis:  Highly Enantioselective Hydrogenations under Mild Conditions
  作者：Philip J. Pye、Kai Rossen、Robert A. Reamer、Nancy N. Tsou、R. P. Volante、Paul J. Reider

  DOI：10.1021/ja970654g

  日期：1997.7.1