[(1R,6S)-8-oxo-7-azabicyclo[4.2.0]oct-3-en-7-yl]methyl butanoate | 285560-91-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: [(1R,6S)-8-oxo-7-azabicyclo[4.2.0]oct-3-en-7-yl]methyl butanoate
• CAS: 285560-91-0
• 化学式: C₁₂H₁₇NO₃
• 分子量: 223.272
• InChiKey: DJKDKHUXMUQTAC-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [(1R,6S)-8-oxo-7-azabicyclo[4.2.0]oct-3-en-7-yl]methyl butanoate 在 盐酸 作用下， 反应 2.0h， 以69 mg的产率得到(1R,6S)-6-氨基-3-环己烯-1-羧酸
  参考文献：
  名称：

  Enzymatic resolution of alicyclic β-lactams

  摘要：

  Racemates of N-hydroxymethylated beta-lactams 4-6 were resolved through the lipase-catalyzed asymmetric acylation of the primary hydroxy group at the 6S stereogenic centre. High enantioselectivity (E > 200) was observed when the enzymatic reactions were performed in acetone with lipase PS as catalyst and vinyl butyrate as acyl donor. The hydrolysis of the enantiomeric azetidinones 4a-6a and 4b-6b resulted in the enantiomerically pure alicyclic beta-amino acids 4c-6c and 4d-6d. When the less reactive enantiomers 4b-6b were treated with NH4OH/MeOH, enantiomerically pure beta-lactams 4e-6e were formed. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00070-7
• 作为产物：
  描述：

  7-azabicyclo[4.2.0]oct-3-en-8-one 、 alkaline earth salt of/the/ methylsulfuric acid 在 Lipase PS 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 9.0h， 生成 [(1R,6S)-8-oxo-7-azabicyclo[4.2.0]oct-3-en-7-yl]methyl butanoate
  参考文献：
  名称：

  Enzymatic resolution of alicyclic β-lactams

  摘要：

  Racemates of N-hydroxymethylated beta-lactams 4-6 were resolved through the lipase-catalyzed asymmetric acylation of the primary hydroxy group at the 6S stereogenic centre. High enantioselectivity (E > 200) was observed when the enzymatic reactions were performed in acetone with lipase PS as catalyst and vinyl butyrate as acyl donor. The hydrolysis of the enantiomeric azetidinones 4a-6a and 4b-6b resulted in the enantiomerically pure alicyclic beta-amino acids 4c-6c and 4d-6d. When the less reactive enantiomers 4b-6b were treated with NH4OH/MeOH, enantiomerically pure beta-lactams 4e-6e were formed. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00070-7

文献信息

• Enzymatic resolution of alicyclic β-lactams
  作者：Judit Kámán、Enikő Forró、Ferenc Fülöp

  DOI：10.1016/s0957-4166(00)00070-7

  日期：2000.4

  Racemates of N-hydroxymethylated beta-lactams 4-6 were resolved through the lipase-catalyzed asymmetric acylation of the primary hydroxy group at the 6S stereogenic centre. High enantioselectivity (E > 200) was observed when the enzymatic reactions were performed in acetone with lipase PS as catalyst and vinyl butyrate as acyl donor. The hydrolysis of the enantiomeric azetidinones 4a-6a and 4b-6b resulted in the enantiomerically pure alicyclic beta-amino acids 4c-6c and 4d-6d. When the less reactive enantiomers 4b-6b were treated with NH4OH/MeOH, enantiomerically pure beta-lactams 4e-6e were formed. (C) 2000 Elsevier Science Ltd. All rights reserved.