3-(4-Fluoro-phenyl)-2-{[1-phenyl-meth-(E)-ylidene]-amino}-propionic acid ethyl ester | 135950-34-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-(4-Fluoro-phenyl)-2-{[1-phenyl-meth-(E)-ylidene]-amino}-propionic acid ethyl ester
• 英文别名: Ethyl 2-(benzylideneamino)-3-(4-fluorophenyl)propanoate
• CAS: 135950-34-4
• 化学式: C₁₈H₁₈FNO₂
• 分子量: 299.345
• InChiKey: FUPSNSMTNMXAGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-Fluoro-phenyl)-2-{[1-phenyl-meth-(E)-ylidene]-amino}-propionic acid ethyl ester 在 水 、 chymotrypsin 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以37%的产率得到L-4-氟苯丙氨酸
  参考文献：
  名称：

  Schiff Bases of Amino Acid Esters as New Substrates for the Enantioselective Enzymatic Hydrolysis and Accompanied Asymmetric Transformations in Aqueous Organic Solvents^1,2

  摘要：

  The enzyme (lipases and chymotrypsin)-catalyzed hydrolysis of Schiff bases derived from racemic amino acid esters and aromatic aldehydes has been investigated. The reactions were successfully carried out in different aqueous organic solvents at ambient temperature, but the aqueous acetonitrile (5.4% water content by volume) was the solvent of choice. The L-amino acid (ee 98%) precipitated out from the solution as the reaction progressed, and the liberated aldehyde and unhydrolyzed D-ester (ee 40-98%) remained in the solution. The range of substrates included amino acids having different types of side chains. The addition of an organic base (DABCO) into the solution resulted in the racemization of the remaining D-ester and the additional hydrolysis of the substrate, thus leading to the effective asymmetric transformation of the initial ester. Upto 87.5% of the initial racemate was converted into the L-enantiomer.

  DOI：

  10.1021/jo941734v
• 作为产物：
  描述：

  ([1-苯基-meth-(e)-基idene]-氨基)-乙酸 乙酯 、 4-氟溴苄 在 sodium hydroxide 、 四丁基溴化铵 作用下， 以 二氯甲烷 为溶剂， 以48%的产率得到3-(4-Fluoro-phenyl)-2-{[1-phenyl-meth-(E)-ylidene]-amino}-propionic acid ethyl ester
  参考文献：
  名称：

  Schiff Bases of Amino Acid Esters as New Substrates for the Enantioselective Enzymatic Hydrolysis and Accompanied Asymmetric Transformations in Aqueous Organic Solvents^1,2

  摘要：

  The enzyme (lipases and chymotrypsin)-catalyzed hydrolysis of Schiff bases derived from racemic amino acid esters and aromatic aldehydes has been investigated. The reactions were successfully carried out in different aqueous organic solvents at ambient temperature, but the aqueous acetonitrile (5.4% water content by volume) was the solvent of choice. The L-amino acid (ee 98%) precipitated out from the solution as the reaction progressed, and the liberated aldehyde and unhydrolyzed D-ester (ee 40-98%) remained in the solution. The range of substrates included amino acids having different types of side chains. The addition of an organic base (DABCO) into the solution resulted in the racemization of the remaining D-ester and the additional hydrolysis of the substrate, thus leading to the effective asymmetric transformation of the initial ester. Upto 87.5% of the initial racemate was converted into the L-enantiomer.

  DOI：

  10.1021/jo941734v

文献信息

• Schiff Bases of Amino Acid Esters as New Substrates for the Enantioselective Enzymatic Hydrolysis and Accompanied Asymmetric Transformations in Aqueous Organic Solvents¹^,²
  作者：Virinder S. Parmar、Amarjit Singh、Kirpal S. Bisht、Naresh Kumar、Y. N. Belokon、K. A. Kochetkov、N. S. Ikonnikov、S. A. Orlova、V. I. Tararov、T. F. Saveleva

  DOI：10.1021/jo941734v

  日期：1996.1.1

  The enzyme (lipases and chymotrypsin)-catalyzed hydrolysis of Schiff bases derived from racemic amino acid esters and aromatic aldehydes has been investigated. The reactions were successfully carried out in different aqueous organic solvents at ambient temperature, but the aqueous acetonitrile (5.4% water content by volume) was the solvent of choice. The L-amino acid (ee 98%) precipitated out from the solution as the reaction progressed, and the liberated aldehyde and unhydrolyzed D-ester (ee 40-98%) remained in the solution. The range of substrates included amino acids having different types of side chains. The addition of an organic base (DABCO) into the solution resulted in the racemization of the remaining D-ester and the additional hydrolysis of the substrate, thus leading to the effective asymmetric transformation of the initial ester. Upto 87.5% of the initial racemate was converted into the L-enantiomer.