(S)-4-Carbamoyl-3-phenyl-butyric acid | 446062-61-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (S)-4-Carbamoyl-3-phenyl-butyric acid
• 英文别名: (3S)-5-amino-5-oxo-3-phenylpentanoic acid
• CAS: 446062-61-9
• 化学式: C₁₁H₁₃NO₃
• 分子量: 207.229
• InChiKey: UGYMJTSIRXZBIB-VIFPVBQESA-N

物化性质

• 沸点：
  462.4±38.0 °C(Predicted)
• 密度：
  1.233±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  80.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-4-Carbamoyl-3-phenyl-butyric acid 在 sodium hydroxide 、 溴 作用下， 以 水 为溶剂， 反应 12.0h， 以100 mg的产率得到4-氨基-3-苯基丁酸盐酸盐
  参考文献：
  名称：

  Enzymatic desymmetrization of 3-alkyl- and 3-arylglutaronitriles, a simple and convenient approach to optically active 4-amino-3-phenylbutanoic acids

  摘要：

  The enantioselective hydrolysis of 3-alkyl- and 3-arylglutaronitriles catalyzed by Rhodococcus sp. AJ270 cells, afforded the corresponding (S)-3-substituted 4-cyanobutanoic acids with low to moderate enantiomeric purities. Additives such as acetone were found to significantly enhance the enantioselectivity of the desymmetrization, giving enantiomeric excesses of up to 95%. The synthetic potential of the homochiral product was also demonstrated by the preparation of optically active (R)- and (S)-4-amino-3-phenylbutanoic acids. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00028-9
• 作为产物：
  描述：

  3-phenylglutaronitrile 在 sodium hydroxide 、 Rhodococcus sp. AJ₂₇₀ cells 、 双氧水 作用下， 以 phosphate buffer 、 水 、 丙酮 为溶剂， 反应 24.0h， 生成 (S)-4-Carbamoyl-3-phenyl-butyric acid
  参考文献：
  名称：

  Enzymatic desymmetrization of 3-alkyl- and 3-arylglutaronitriles, a simple and convenient approach to optically active 4-amino-3-phenylbutanoic acids

  摘要：

  The enantioselective hydrolysis of 3-alkyl- and 3-arylglutaronitriles catalyzed by Rhodococcus sp. AJ270 cells, afforded the corresponding (S)-3-substituted 4-cyanobutanoic acids with low to moderate enantiomeric purities. Additives such as acetone were found to significantly enhance the enantioselectivity of the desymmetrization, giving enantiomeric excesses of up to 95%. The synthetic potential of the homochiral product was also demonstrated by the preparation of optically active (R)- and (S)-4-amino-3-phenylbutanoic acids. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00028-9

文献信息

• Biocatalytic Desymmetrization of Prochiral 3-Aryl and 3-Arylmethyl Glutaramides: Different Remote Substituent Effect on Catalytic Efficiency and Enantioselectivity
  作者：Yu-Fei Ao、Li-Bin Zhang、Qi-Qiang Wang、De-Xian Wang、Mei-Xiang Wang

  DOI：10.1002/adsc.201800956

  日期：2018.12.3

  efficiently afforded 3‐substituted glutaric acid monoamides in up to 95% yield and >99.5% ee. Even far away from the reaction site, the substituents on the aryl still have a significant effect on the catalytic activity and enantioselectivity and different remote substituent effect was observed for the two types of substrates. The synthetic application of biocatalytic desymmetrization was demonstrated by

  在30°C下于中性磷酸盐缓冲液中用含酰胺酶的红球菌红球菌AJ270微生物全细胞催化剂催化，一系列前手性3-芳基和3-芳基甲基戊二酰胺的不对称水解有效地提供了3-取代的戊二酸单酰胺，收率高达95％和> 99.5％ee。甚至远离反应位点，芳基上的取代基仍然对催化活性和对映选择性具有显着影响，并且对于两种类型的底物观察到不同的远程取代基效果。获得的对映纯（R）-3-取代的4-氨基甲酰基丁酸产物轻松转化为手性二氢喹啉酮和δ证明了生物催化脱对称的合成应用内酯化合物。