(1S,6R)-7-羟甲基-7-氮杂双环[4.2.0]辛烷-8-酮 | 285560-93-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 中文名称: (1S,6R)-7-羟甲基-7-氮杂双环[4.2.0]辛烷-8-酮
• 英文名称: (1S,6R)-7-hydroxymethyl-7-azabicyclo[4.2.0]octan-8-one
• 英文别名: (1S,6R)-7-(hydroxymethyl)-7-azabicyclo[4.2.0]octan-8-one
• CAS: 285560-93-2
• 化学式: C₈H₁₃NO₂
• 分子量: 155.197
• InChiKey: IDMHNEFAJXWNEI-NKWVEPMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,6R)-7-羟甲基-7-氮杂双环[4.2.0]辛烷-8-酮 在 盐酸 作用下， 反应 2.0h， 以0.1 g的产率得到(1RS,2SR)-2-aminocyclohexanecarboxylic acid
  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-hydroxymethyl-7-azabicyclo[4.2.0]octan-8-one 在 Lipase PS 、 正丁酸乙烯酯 作用下， 以 丙酮 为溶剂， 反应 5.0h， 生成 (1S,6R)-7-羟甲基-7-氮杂双环[4.2.0]辛烷-8-酮
  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

• Hairpin Folding Behavior of Mixed α/β-Peptides in Aqueous Solution
  作者：George A. Lengyel、Rebecca C. Frank、W. Seth Horne

  DOI：10.1021/ja2002346

  日期：2011.3.30

  The invention of new strategies for the design of protein-mimetic oligomers that manifest the folding encoded in natural amino acid sequences is a significant challenge. In contrast to the a-helix, mimicry of protein beta-sheets is less understood. We report here the aqueous folding behavior of a prototype alpha-peptide hairpin model sequence varied at cross-strand positions by incorporation of 16 different beta-amino acid monomers. Our results provide a folding propensity scale for beta-residues in a protein beta-sheet context as well as high-resolution structures of several mixed-backbone alpha/beta-peptide hairpins in water.
• 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.