(7aS)-tert-butyl 3-amino-5,6,7,7a-tetrahydro-1-oxo-1H-pyrrolizine-2-carboxylate | 866572-51-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯嗪
• 英文名称: (7aS)-tert-butyl 3-amino-5,6,7,7a-tetrahydro-1-oxo-1H-pyrrolizine-2-carboxylate
• 英文别名: tert-butyl (8S)-3-amino-1-oxo-5,6,7,8-tetrahydropyrrolizine-2-carboxylate
• CAS: 866572-51-2
• 化学式: C₁₂H₁₈N₂O₃
• 分子量: 238.287
• InChiKey: NRFUFFDBYHKDOD-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.55
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  72.63
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (7aS)-tert-butyl 3-amino-5,6,7,7a-tetrahydro-1-oxo-1H-pyrrolizine-2-carboxylate 在 silica gel 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 20.0h， 生成 tert-butyl 3-amino-5,6,7,7a-tetrahydro-7a-methoxy-1-oxo-1H-pyrrolizine-2-carboxylate
  参考文献：
  名称：

  Structure Reassignment and Synthesis of Jenamidines A₁/A₂, Synthesis of (+)-NP25302, and Formal Synthesis of SB-311009 Analogues

  摘要：

  and C (8-10). Jenamidines A(1)/A(2) (8) were synthesized from activated proline derivative 43 by conversion to 26 in two steps and 50% overall yield. Acylation of 26 with acid chloride 38d gave 39d, which was deprotected with TFA and then mild base to give 8 in 45% yield from 26. (-)-trans-2,5-Dimethylproline ethyl ester (49) was prepared by the enantioselective Michael reaction of ethyl 2-nitropropionate (51) and methyl vinyl ketone (50) using modified dihydroquinine 60 as the catalyst. Further elaboration converted 49 to natural (+)-NP25302 (12). A Wittig reaction of proline NCA ( 76) with ylide 79 gave 72 as a 9/1 E/Z mixture in 27% yield, completing a one-step formal synthesis of SB-311009 analogues.

  DOI：

  10.1021/jo061650+
• 作为产物：
  描述：

  N-苄氧羰基-L-脯氨酸 N-羟基琥珀酰亚胺酯 在 palladium on activated charcoal 氢气 、 sodium hydride 作用下， 以 甲醇 、 苯 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 30.0h， 生成 (7aS)-tert-butyl 3-amino-5,6,7,7a-tetrahydro-1-oxo-1H-pyrrolizine-2-carboxylate
  参考文献：
  名称：

  Structure Reassignment and Synthesis of Jenamidines A₁/A₂, Synthesis of (+)-NP25302, and Formal Synthesis of SB-311009 Analogues

  摘要：

  and C (8-10). Jenamidines A(1)/A(2) (8) were synthesized from activated proline derivative 43 by conversion to 26 in two steps and 50% overall yield. Acylation of 26 with acid chloride 38d gave 39d, which was deprotected with TFA and then mild base to give 8 in 45% yield from 26. (-)-trans-2,5-Dimethylproline ethyl ester (49) was prepared by the enantioselective Michael reaction of ethyl 2-nitropropionate (51) and methyl vinyl ketone (50) using modified dihydroquinine 60 as the catalyst. Further elaboration converted 49 to natural (+)-NP25302 (12). A Wittig reaction of proline NCA ( 76) with ylide 79 gave 72 as a 9/1 E/Z mixture in 27% yield, completing a one-step formal synthesis of SB-311009 analogues.

  DOI：

  10.1021/jo061650+

文献信息

• Structure Reassignment and Synthesis of Jenamidines A₁/A₂, Synthesis of (+)-NP25302, and Formal Synthesis of SB-311009 Analogues
  作者：Jeremy R. Duvall、Fanghui Wu、Barry B. Snider

  DOI：10.1021/jo061650+

  日期：2006.10.1

  and C (8-10). Jenamidines A(1)/A(2) (8) were synthesized from activated proline derivative 43 by conversion to 26 in two steps and 50% overall yield. Acylation of 26 with acid chloride 38d gave 39d, which was deprotected with TFA and then mild base to give 8 in 45% yield from 26. (-)-trans-2,5-Dimethylproline ethyl ester (49) was prepared by the enantioselective Michael reaction of ethyl 2-nitropropionate (51) and methyl vinyl ketone (50) using modified dihydroquinine 60 as the catalyst. Further elaboration converted 49 to natural (+)-NP25302 (12). A Wittig reaction of proline NCA ( 76) with ylide 79 gave 72 as a 9/1 E/Z mixture in 27% yield, completing a one-step formal synthesis of SB-311009 analogues.