2-甲氧基甲基-3-苯基丙腈 | 1013032-70-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-甲氧基甲基-3-苯基丙腈
• 英文名称: 2-methoxymethyl-3-phenylpropionitrile
• 英文别名: 2-Benzyl-3-methoxypropanenitrile
• CAS: 1013032-70-6
• 化学式: C₁₁H₁₃NO
• 分子量: 175.23
• InChiKey: XGCLSZYZWIEZFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-甲氧基甲基-3-苯基丙腈 在 Rhodococcus erythropolis AJ₂₇₀ cells 作用下， 以 phosphate buffer 为溶剂， 反应 168.0h， 以50%的产率得到(S)-2-methoxymethyl-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
• 作为产物：
  描述：

  2-苄基-3-羟基丙腈 、 碘甲烷 在 silver(l) oxide 作用下， 以 乙腈 为溶剂， 以77%的产率得到2-甲氧基甲基-3-苯基丙腈
  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

文献信息

• 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
  作者：Da-You Ma、De-Xian Wang、Jie Pan、Zhi-Tang Huang、Mei-Xiang Wang

  DOI：10.1016/j.tetasy.2008.01.017

  日期：2008.2

  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.