methyl N-[(2R)-3-cyano-2-phenylpropyl]carbamate | 321125-73-9

• 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: methyl N-[(2R)-3-cyano-2-phenylpropyl]carbamate
• CAS: 321125-73-9
• 化学式: C₁₂H₁₄N₂O₂
• 分子量: 218.255
• InChiKey: KNIUVJYXAVKPEJ-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  62.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl N-[(2R)-3-cyano-2-phenylpropyl]carbamate 在 盐酸 作用下， 以 水 为溶剂， 反应 48.0h， 以34%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 Rhodococcus sp. AJ₂₇₀ cells 、 氯甲酸乙酯 、 三乙胺 作用下， 以 phosphate buffer 、 丙酮 为溶剂， 反应 31.5h， 生成 methyl N-[(2R)-3-cyano-2-phenylpropyl]carbamate
  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

• Microbial desymmetrization of 3-arylglutaronitriles, an unusual enhancement of enantioselectivity in the presence of additives
  作者：Mei-Xiang Wang、Chu-Sheng Liu、Ji-Sheng Li、Otto Meth-Cohn

  DOI：10.1016/s0040-4039(00)01518-5

  日期：2000.10

  3-arylglutaronitriles catalyzed by Rhodococcus sp. AJ270 cells proceeded regiospecifically and enantioselectively to produce S-(+)-3-aryl-4-cyanobutyric acids in high enantiomeric excess. Convenient chemoenzymatic syntheses of optically active R-(−)-4-amino-3-phenylbutyric acid and 4R-(−)-4-phenyltetrahydropyran-2-one are described.

  在有机添加剂（例如丙酮或β-环糊精）的存在下，或在己烷和磷酸盐缓冲液的双相系统中，红球菌（Rhodococcus sp。）催化3-芳基戊二腈的微生物脱对称化。AJ270细胞在区域特异性和对映体选择性上产生高对映体过量的S -（+）-3-芳基-4-氰基丁酸。描述了光学活性R -（-）-4-氨基-3-苯基丁酸和4 R -（-）-4-苯基四氢吡喃-2-酮的便捷化学酶促合成。