(S)-2-(3-Amino-benzyl)-butyric acid | 138809-55-9

• 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)-2-(3-Amino-benzyl)-butyric acid
• 英文别名: (2S)-2-[(3-aminophenyl)methyl]butanoic acid
• CAS: 138809-55-9
• 化学式: C₁₁H₁₅NO₂
• 分子量: 193.246
• InChiKey: ZRRVWPUAOKIETO-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 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：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-(3-Amino-benzyl)-butyric acid 在 盐酸 、 一氯化碘 作用下， 反应 1.0h， 生成 (S)-(+)-iopanoic acid 、 (R)-(-)-iopanoic acid
  参考文献：
  名称：

  Chemoenzymatic synthesis of the enantiomers of iopanoic acid

  摘要：

  The two enantiomers of Iopanoic acid 1 were prepared in enantiomeric excess higher than 90% by enzyme-catalyzed hydrolysis of precursors (+/-)-2a and (+/-)-3a, followed by standard chemical transformations. Among the tested enzymes, chymotrypsin and Lipase PS proved to be the most selective catalysts. The stereochemical outcome of the lipase-catalyzed hydrolyses of esters (+/-)-2a-d is strictly dependent upon both the size of the alkyl group attached to the chiral center and the substituent in the aromatic ring. The enantioselectivity of the reactions was evaluated by chiral HPLC and the configurations of the new products were assigned by chemical correlations.

  DOI：

  10.1016/s0957-4166(00)86152-2
• 作为产物：
  描述：

  3-氨基苯基-2-乙基丙酸甲酯 在 potassium phosphate buffer 作用下， 反应 48.0h， 生成 (2R)-2-[(3-aminophenyl)methyl]butanoic acid 、 (S)-2-(3-Amino-benzyl)-butyric acid
  参考文献：
  名称：

  Chemoenzymatic synthesis of the enantiomers of iopanoic acid

  摘要：

  The two enantiomers of Iopanoic acid 1 were prepared in enantiomeric excess higher than 90% by enzyme-catalyzed hydrolysis of precursors (+/-)-2a and (+/-)-3a, followed by standard chemical transformations. Among the tested enzymes, chymotrypsin and Lipase PS proved to be the most selective catalysts. The stereochemical outcome of the lipase-catalyzed hydrolyses of esters (+/-)-2a-d is strictly dependent upon both the size of the alkyl group attached to the chiral center and the substituent in the aromatic ring. The enantioselectivity of the reactions was evaluated by chiral HPLC and the configurations of the new products were assigned by chemical correlations.

  DOI：

  10.1016/s0957-4166(00)86152-2

文献信息

• Chemoenzymatic synthesis of the enantiomers of iopanoic acid
  作者：M. Colombo、M. De Amici、C. De Micheli、D. Pitré、G. Carrea、S. Riva

  DOI：10.1016/s0957-4166(00)86152-2

  日期：1991.1

  The two enantiomers of Iopanoic acid 1 were prepared in enantiomeric excess higher than 90% by enzyme-catalyzed hydrolysis of precursors (+/-)-2a and (+/-)-3a, followed by standard chemical transformations. Among the tested enzymes, chymotrypsin and Lipase PS proved to be the most selective catalysts. The stereochemical outcome of the lipase-catalyzed hydrolyses of esters (+/-)-2a-d is strictly dependent upon both the size of the alkyl group attached to the chiral center and the substituent in the aromatic ring. The enantioselectivity of the reactions was evaluated by chiral HPLC and the configurations of the new products were assigned by chemical correlations.