(RS)-4-cyano-4-(3,4-dimethoxyphenyl)-4-isopropylbutyl acetate | 255721-20-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (RS)-4-cyano-4-(3,4-dimethoxyphenyl)-4-isopropylbutyl acetate
• 英文别名: [4-Cyano-4-(3,4-dimethoxyphenyl)-5-methylhexyl] acetate
• CAS: 255721-20-1
• 化学式: C₁₈H₂₅NO₄
• 分子量: 319.401
• InChiKey: XSWYZLLMJLRFFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  68.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (RS)-4-cyano-4-(3,4-dimethoxyphenyl)-4-isopropylbutyl acetate 在 sodium hydroxide 、 phosphate buffer 、 pseudomonas fluorescens lipase 作用下， 生成 (2S)-(-)-2-(3,4-dimethoxyphenyl)-5-hydroxy-2-isopropylpentanenitrile
  参考文献：
  名称：

  Enzyme-catalysed improved resolution of (RS)-4-cyano-4-(3,4-dimethoxyphenyl)-4-isopropyl-1-butanol

  摘要：

  Resolutions of (RS)-4-cyano-4-(3,4-dimethoxyphenyl)-4-isopropyl-1-butanol 1 using various enzymes were performed. Among them, Pseudomonas fluorescens resolved it with moderate stereoselectivity (E=13) and reacted faster with the (S)-enantiomer. To optimize enzyme-catalysed reaction conditions for the resolution, the effect of solvents and additives was studied. In n-hexane:ethyl acetate (9:1), both reaction rate and selectivity were high. When pyridine, potassium carbonate and molecular sieves were used as additives, the enantiomeric excess of the (R)-enantiomer was 99, 99 and 98% at 52-60% conversion, respectively. However, in diisopropyl ether, the enantiomeric excess of unreacted alcohol (R)-1 was up to 99% at 70% conversion without additives. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00389-4
• 作为产物：
  描述：

  3-甲基-2-(3,4-二甲氧基苯基)丁腈 在 吡啶 、 盐酸 、 甲醇 、 4-二甲氨基吡啶 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.5h， 生成 (RS)-4-cyano-4-(3,4-dimethoxyphenyl)-4-isopropylbutyl acetate
  参考文献：
  名称：

  Enzyme-catalysed improved resolution of (RS)-4-cyano-4-(3,4-dimethoxyphenyl)-4-isopropyl-1-butanol

  摘要：

  Resolutions of (RS)-4-cyano-4-(3,4-dimethoxyphenyl)-4-isopropyl-1-butanol 1 using various enzymes were performed. Among them, Pseudomonas fluorescens resolved it with moderate stereoselectivity (E=13) and reacted faster with the (S)-enantiomer. To optimize enzyme-catalysed reaction conditions for the resolution, the effect of solvents and additives was studied. In n-hexane:ethyl acetate (9:1), both reaction rate and selectivity were high. When pyridine, potassium carbonate and molecular sieves were used as additives, the enantiomeric excess of the (R)-enantiomer was 99, 99 and 98% at 52-60% conversion, respectively. However, in diisopropyl ether, the enantiomeric excess of unreacted alcohol (R)-1 was up to 99% at 70% conversion without additives. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00389-4