(3S)-3-amino-3-(4-methoxyphenyl)propanenitrile | 1228554-04-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (3S)-3-amino-3-(4-methoxyphenyl)propanenitrile
• CAS: 1228554-04-8
• 化学式: C₁₀H₁₂N₂O
• 分子量: 176.218
• InChiKey: XUXIWRVFCJZXKR-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-甲氧基苯甲腈 在 盐酸 、 potassium tert-butylate 、 水 、 sodium cyanoborohydride 作用下， 以 甲醇 、 乙醇 、 to\\ 、 水 为溶剂， 反应 27.0h， 生成 (3R)-3-amino-3-(4-methoxyphenyl)propanenitrile 、 (3S)-3-amino-3-(4-methoxyphenyl)propanenitrile 、 (3R)-3-amino-3-(4-methoxyphenyl)propanamide 、 (3S)-3-amino-3-(4-methoxyphenyl)propanamide
  参考文献：
  名称：

  Enantioselective biocatalytic hydrolysis of β-aminonitriles to β-amino-amides using Rhodococcus rhodochrous ATCC BAA-870

  摘要：

  A range of beta-aminonitriles (3-amino-3-phenylpropanenitrile and derivatives) were synthesised by reaction of various benzonitriles with acetonitrile and subsequent reduction of the resulting acrylonitrile products. These compounds were hydrolysed to the corresponding amides using the nitrile biocatalytic activity of Rhodococccus rhodochrous ATCC BAA-870. Results showed that the nitrile hydratase enzyme was enantioselective for these compounds, in particular 3-amino-3-p-tolylpropanenitrile and 3-amino-3-(4-methoxyphenyl)propanenitrile and the corresponding amides (up to 85% in one case). The reactions were performed at pH 9.0 after initial attempts at pH 7.0 were unsuccessful, most likely as a result of protonation of the 3-amino group at the lower pH. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2011.12.005