(S)-2-Benzoyl-3-prop-(Z)-ylidene-hexahydro-pyrrolo[1,2-a]pyrazine-1,4-dione | 145038-61-5

• 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: (S)-2-Benzoyl-3-prop-(Z)-ylidene-hexahydro-pyrrolo[1,2-a]pyrazine-1,4-dione
• 英文别名: (3Z,8aS)-2-benzoyl-3-propylidene-6,7,8,8a-tetrahydropyrrolo[1,2-a]pyrazine-1,4-dione
• CAS: 145038-61-5
• 化学式: C₁₇H₁₈N₂O₃
• 分子量: 298.342
• InChiKey: ZNUHCXOEONCITN-GRFABLRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 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：

  (S)-2-Benzoyl-3-prop-(Z)-ylidene-hexahydro-pyrrolo[1,2-a]pyrazine-1,4-dione 在 甘氨酸甲酯盐酸盐 、 三乙胺 作用下， 以 乙醚 、 苯 为溶剂， 反应 288.0h， 生成 tert-butyl (5S,8'aS)-4-ethyl-1',4'-dioxospiro[3,4-dihydropyrazole-5,3'-6,7,8,8a-tetrahydropyrrolo[1,2-a]pyrazine]-2'-carboxylate
  参考文献：
  名称：

  Enantioselective synthesis of (+)-(1R,2S)-allocoronamic acid

  摘要：

  The asymmetric synthesis of (+)-(1R,2S)-allocoronamic acid is reported. Diazomethane addition to (Z)-N-(tert-butoxycarbonyl)ethyldehydroalanyl-L-prolin-anhydride, easily prepared from (Z)-2-phenyl-4-propylidene-5(4H)-oxazolone and L-proline, gave in high diastereomeric excess the corresponding spiropyrazoline, which was transformed, on photolysis and acid hydrolysis of the resulting spirocyclopropane, into (+)-(1R,2S)-1-amino-2-ethyl-cyclopropanecarboxylic acid.

  DOI：

  10.1016/s0040-4039(00)61159-0
• 作为产物：
  描述：

  (Z)-2-phenyl-4-propylidene-5(4H)-oxazolone 、 L-脯氨酸 在 sodium hydroxide 、 乙酸酐 作用下， 生成 (S)-2-Benzoyl-3-prop-(Z)-ylidene-hexahydro-pyrrolo[1,2-a]pyrazine-1,4-dione
  参考文献：
  名称：

  Enantioselective synthesis of (+)-(1R,2S)-allocoronamic acid

  摘要：

  The asymmetric synthesis of (+)-(1R,2S)-allocoronamic acid is reported. Diazomethane addition to (Z)-N-(tert-butoxycarbonyl)ethyldehydroalanyl-L-prolin-anhydride, easily prepared from (Z)-2-phenyl-4-propylidene-5(4H)-oxazolone and L-proline, gave in high diastereomeric excess the corresponding spiropyrazoline, which was transformed, on photolysis and acid hydrolysis of the resulting spirocyclopropane, into (+)-(1R,2S)-1-amino-2-ethyl-cyclopropanecarboxylic acid.

  DOI：

  10.1016/s0040-4039(00)61159-0

文献信息

• Enantioselective synthesis of (+)-(1R,2S)-allocoronamic acid
  作者：Carmen Alcaraz、Angela Herrero、José L. Marco、Eldiberto Fernández-Alvarez、Manuel Bernabé

  DOI：10.1016/s0040-4039(00)61159-0

  日期：1992.9

  The asymmetric synthesis of (+)-(1R,2S)-allocoronamic acid is reported. Diazomethane addition to (Z)-N-(tert-butoxycarbonyl)ethyldehydroalanyl-L-prolin-anhydride, easily prepared from (Z)-2-phenyl-4-propylidene-5(4H)-oxazolone and L-proline, gave in high diastereomeric excess the corresponding spiropyrazoline, which was transformed, on photolysis and acid hydrolysis of the resulting spirocyclopropane, into (+)-(1R,2S)-1-amino-2-ethyl-cyclopropanecarboxylic acid.