(1R,12R)-13-azabicyclo[10.2.0]tetradecan-14-one | 929296-23-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: (1R,12R)-13-azabicyclo[10.2.0]tetradecan-14-one
• CAS: 929296-23-1
• 化学式: C₁₃H₂₃NO
• 分子量: 209.332
• InChiKey: QZGCOFZRRZPWHB-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1R,12R)-13-azabicyclo[10.2.0]tetradecan-14-one 在 盐酸 作用下， 以 水 为溶剂， 反应 3.0h， 以79%的产率得到
  参考文献：
  名称：

  Do lipases also catalyse the ring cleavage of inactivated cyclic trans-β-lactams?

  摘要：

  Twelve-membered cyclic cis- and trans-beta-lactams 1b and 2b and the corresponding cyclic cis- and trans-beta-amino acid enantiomers, 1a, 1e and 2a, 2c were prepared through the CAL-B-catalysed enantio selective ring cleavage of racemic cis-13-azabicyclo[10.2.0]tetradecan-14-one, (+/-)-1, and trans-13-azabicyclo[10.2.0]tetradecan-14-one, (+/-)-2. High enantioselectivities (E > 200) were observed for the ring opening of both the cis- and trans-beta-lactams when the Lipolase-catalysed reactions were performed with 0.5 equiv of H2O in i-Pr2O at 70 degrees C. The resolved beta-lactams 1b and 2b (yield >= 47%) and beta-amino acids 1a and 2a (yield >= 32%) could be easily separated. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2006.11.030
• 作为产物：
  描述：

  trans-13-azabicyclo[10.2.0]tetradecan-14-one 在 Lipolase C_. antarctica lipase B 作用下， 以 异丙醚 、 水 为溶剂， 反应 99.0h， 以41%的产率得到(1S,2S)-2-aminocyclododecane-1-carboxylic acid
  参考文献：
  名称：

  Do lipases also catalyse the ring cleavage of inactivated cyclic trans-β-lactams?

  摘要：

  Twelve-membered cyclic cis- and trans-beta-lactams 1b and 2b and the corresponding cyclic cis- and trans-beta-amino acid enantiomers, 1a, 1e and 2a, 2c were prepared through the CAL-B-catalysed enantio selective ring cleavage of racemic cis-13-azabicyclo[10.2.0]tetradecan-14-one, (+/-)-1, and trans-13-azabicyclo[10.2.0]tetradecan-14-one, (+/-)-2. High enantioselectivities (E > 200) were observed for the ring opening of both the cis- and trans-beta-lactams when the Lipolase-catalysed reactions were performed with 0.5 equiv of H2O in i-Pr2O at 70 degrees C. The resolved beta-lactams 1b and 2b (yield >= 47%) and beta-amino acids 1a and 2a (yield >= 32%) could be easily separated. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2006.11.030

文献信息

• Do lipases also catalyse the ring cleavage of inactivated cyclic trans-β-lactams?
  作者：Enikő Forró、Ferenc Fülöp

  DOI：10.1016/j.tetasy.2006.11.030

  日期：2006.12

  Twelve-membered cyclic cis- and trans-beta-lactams 1b and 2b and the corresponding cyclic cis- and trans-beta-amino acid enantiomers, 1a, 1e and 2a, 2c were prepared through the CAL-B-catalysed enantio selective ring cleavage of racemic cis-13-azabicyclo[10.2.0]tetradecan-14-one, (+/-)-1, and trans-13-azabicyclo[10.2.0]tetradecan-14-one, (+/-)-2. High enantioselectivities (E > 200) were observed for the ring opening of both the cis- and trans-beta-lactams when the Lipolase-catalysed reactions were performed with 0.5 equiv of H2O in i-Pr2O at 70 degrees C. The resolved beta-lactams 1b and 2b (yield >= 47%) and beta-amino acids 1a and 2a (yield >= 32%) could be easily separated. (c) 2006 Published by Elsevier Ltd.