(S)-2-allyloxymethyl-3-phenylpropionamide | 1013032-77-3

• 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: (S)-2-allyloxymethyl-3-phenylpropionamide
• CAS: 1013032-77-3
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: PVIAPUKECRBCCQ-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.53
• 重原子数：
  16.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  52.32
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  在 Rhodococcus erythropolis AJ₂₇₀ cells 作用下， 以 phosphate buffer 为溶剂， 反应 168.0h， 生成 (S)-2-allyloxymethyl-3-phenylpropionic acid 、 (R)-2-allyloxymethyl-3-phenylpropionic acid 、 (S)-2-allyloxymethyl-3-phenylpropionamide 、 (R)-2-allyloxymethyl-3-phenylpropionamide
  参考文献：
  名称：

  Nitrile biotransformations for the synthesis of enantiomerically enriched β2-, and β3-hydroxy and -alkoxy acids and amides, a dramatic O-substituent effect of the substrates on enantioselectivity

  摘要：

  Rhodococcus erythropolis AJ270, a nitrile hydratase/amidase-containing microbial whole cell catalyst, is able to catalyze the hydrolysis of a number of P-hydroxy and beta-alkoxy nitriles under very mild conditions. Both the efficiency and enantio selectivity of the biocatalysis. however, were strongly dependent upon the structures of both nitrile and amide substrates. When biotransformations of racemic 3-hydroxy-3-phenylpropionitrile and 2-hydroxymethyl-3-phenylpropionitrile gave low enantioselectivity, their O-methylated isomers underwent highly efficient and enantio selective biocatalytic reactions to afford highly enantioenriched beta(2)- and beta(3)-hydroxy amide and acid derivatives in excellent yield. The study has provided an example of simple and very convenient substrate engineering method to increase the enantioselectivity of the biocatalytic reaction. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.01.017