Octanoic acid ((1S,2R)-2-octanoylamino-cyclohexyl)-amide

• 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: Octanoic acid ((1S,2R)-2-octanoylamino-cyclohexyl)-amide
• 英文别名: N-[(1S,2R)-2-(octanoylamino)cyclohexyl]octanamide
• 化学式: C₂₂H₄₂N₂O₂
• 分子量: 366.588
• InChiKey: NHUKVDOWBNNVFH-BGYRXZFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.25
• 重原子数：
  26.0
• 可旋转键数：
  14.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  58.2
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  辛酸乙酯 、 1,2-二氨基环己烷 生成 Octanoic acid ((1R,2R)-2-octanoylamino-cyclohexyl)-amide 、 Octanoic acid ((1S,2S)-2-octanoylamino-cyclohexyl)-amide 、 Octanoic acid ((1S,2R)-2-octanoylamino-cyclohexyl)-amide
  参考文献：
  名称：

  Kinetic Resolution of Chiral Auxiliaries with C2-Symmetry by Lipase-Catalyzed Alcoholysis and Aminolysis.

  摘要：

  Three cyclic diols, 1,2-cyclohexanediol (1), 1,3-cyclohexanediol (2), and 1,3-cyclopentanediol (3), two acyclic unsaturated diols, 1,5-hexadiene-3,4-diol (4) and 1,7-octadiyne-3,6-diol (5), and a cyclic diamine, 1,2-cyclohexanediamine (6), have been kinetically resolved in alcoholysis and aminolysis reactions, catalyzed by Candida antarctica component B lipase, using S-ethyl thiooctanoate or ethyl octanoate as acyl donors. Acceptable stereoselectivity was achieved in most cases.

  DOI：

  10.3891/acta.chem.scand.50-0918

文献信息

• Kinetic Resolution of Chiral Auxiliaries with C2-Symmetry by Lipase-Catalyzed Alcoholysis and Aminolysis.
  作者：Anders Mattson、Christian Orrenius、Niklas Öhrner、C. Rikard Unelius、Karl Hult、Torbjörn Norin、Muhammed Nour Homsi、Frank K. H. Kuske、Monika Haugg、Nathalie Trabesinger-Rüf、Elmar G. Weinhold

  DOI：10.3891/acta.chem.scand.50-0918

  日期：——

  Three cyclic diols, 1,2-cyclohexanediol (1), 1,3-cyclohexanediol (2), and 1,3-cyclopentanediol (3), two acyclic unsaturated diols, 1,5-hexadiene-3,4-diol (4) and 1,7-octadiyne-3,6-diol (5), and a cyclic diamine, 1,2-cyclohexanediamine (6), have been kinetically resolved in alcoholysis and aminolysis reactions, catalyzed by Candida antarctica component B lipase, using S-ethyl thiooctanoate or ethyl octanoate as acyl donors. Acceptable stereoselectivity was achieved in most cases.