2-[(1S,5R)-5-hydroxycyclopent-2-en-1-yl]-N,N-dimethylacetamide | 138232-58-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-[(1S,5R)-5-hydroxycyclopent-2-en-1-yl]-N,N-dimethylacetamide
• CAS: 138232-58-3
• 化学式: C₉H₁₅NO₂
• 分子量: 169.224
• InChiKey: KCABZZVEKBHZLB-HTQZYQBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  辛酸乙烯酯 、 2-[(1S,5R)-5-hydroxycyclopent-2-en-1-yl]-N,N-dimethylacetamide 以 异丙醚 为溶剂， 生成 Octanoic acid (1R,2S)-2-dimethylcarbamoylmethyl-cyclopent-3-enyl ester
  参考文献：
  名称：

  Significant effect of acyl groups on enantioselectivity in lipase-catalyzed transesterifications

  摘要：

  The effect of the acyl group of acylating agents on the enantioselectivity in the lipase-catalyzed transesterifications of racemic 2-[(N,N-dimethylcarbamoyl)methyl]-3-cyclopenten-1-ol in diisopropyl ether was found to be significant. The enantioselectivity was enhanced markedly by changing the acylating agent from vinyl acetate to vinyl butyrate, and dropped substantially with longer acyl donors. Other acyl donors were also examined. (C) 1996 Published by Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00049-3
• 作为产物：
  描述：

  辛酸乙烯酯 、 2-(5-hydroxycyclopent-2-en-1-yl)-N,N-dimethylacetamide 在 Lipase PS 作用下， 以 异丙醚 为溶剂， 反应 2.0h， 生成 2-[(1S,5R)-5-hydroxycyclopent-2-en-1-yl]-N,N-dimethylacetamide 、 2-[(1R,5S)-5-hydroxycyclopent-2-en-1-yl]-N,N-dimethylacetamide 、 Octanoic acid (1R,2S)-2-dimethylcarbamoylmethyl-cyclopent-3-enyl ester 、 Octanoic acid (1S,2R)-2-dimethylcarbamoylmethyl-cyclopent-3-enyl ester
  参考文献：
  名称：

  Kinetic Resolution of Racemic 2-Substituted 3-Cyclopenten-1-ols by Lipase-Catalyzed Transesterifications:  A Rational Strategy To Improve Enantioselectivity

  摘要：

  The effect of the acyl group of acylating agents on the enantioselectivity in the Pseudomonas cepacia lipase-catalyzed acylations of racemic alcohols has been studied. 2-[(N,N-Dimethylcarbamoyl)methyl]-3-cyclopenten-1-ol (1) and 2-[2-(tert-butyldimethylsilyloxy)ethyl]-3-cyclopenten-1-ol (4) were resolved with a variety of enantioselectivities. In the case of alcohol 1, the enantiomeric ratio (the E value) was increased by changing the acylating agent from vinyl acetate (E = 30) to vinyl butyrate (E = 156) and dropped substantially with longer acyl donors. With vinyl chloroacetate, the reaction rate was fast and the enantioselectivity was high (E = 89), whereas the resolution with vinyl trifluoroacetate resulted in a very poor enantioselectivity (E = 4). The bulky acylating agent, vinyl pivalate, gave a moderate enantioselectivity (E = 15). In the case of alcohol 4, the enantioselectivities were excellent (E > 142) except vinyl pivalate (E = 12). It is indicated that the acyl group transiently attached at the active site of the lipase acts as a stereochemical controller. The solvent effect is also described briefly. A clear correlation was observed between the E values and the log P values of the organic solvents; the smaller the log P value of the solvent, the higher the E value.

  DOI：

  10.1021/jo961144s