methyl 1-acetyl-1,4,5,6-tetrahydropyrazine-2-carboxylate | 171504-81-7

• 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: methyl 1-acetyl-1,4,5,6-tetrahydropyrazine-2-carboxylate
• 英文别名: methyl 4-acetyl-2,3-dihydro-1H-pyrazine-5-carboxylate
• CAS: 171504-81-7
• 化学式: C₈H₁₂N₂O₃
• 分子量: 184.195
• InChiKey: KTIHAXUVHMDOCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  乙酸酐 、 甲基1,4,5,6-四氢-2-吡嗪羧酸酯 生成 methyl 1-acetyl-1,4,5,6-tetrahydropyrazine-2-carboxylate
  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

• Process for the preparation of optically active piperazine-2-carboxylic
  申请人：Lonza, Ltd.

  公开号：US05886181A1

  公开（公告）日：1999-03-23

  Optically active piperazine-2-carboxylic acid derivatives of the general formula: ##STR1## wherein R.sup.1 and R.sup.2 are inter alia hydrogen, alkyl or acyl and X is alkoxy or a (substituted) amino group, are prepared by asymmetric hydrogenation of the corresponding 1,4,5,6-tetrahydropyrazines, catalyzed by optically active rhodium, ruthenium or iridium complexes. The compounds of the Formula 1 are intermediates for the preparation of pharmaceutical active ingredients, for example, HIV protease inhibitors.

  光学活性的哌嗪-2-羧酸衍生物，其一般公式为：##STR1## 其中R.sup.1和R.sup.2是氢、烷基或酰基，X是烷氧基或（取代）氨基团，是通过相应的1,4,5,6-四氢吡嗪的光学活性铑、钌或铱络合物催化的不对称氢化反应来制备的。公式1的化合物是用于制备药物活性成分的中间体，例如，HIV蛋白酶抑制剂。
• US5886181A
  申请人：——

  公开号：US5886181A

  公开（公告）日：1999-03-23
• 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.