N-Chloracetyl-β-2-thienyl-DL-β-alanin | 67206-29-5

• 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: N-Chloracetyl-β-2-thienyl-DL-β-alanin
• 英文别名: 3-[(2-Chloroacetyl)amino]-3-thiophen-2-ylpropanoic acid
• CAS: 67206-29-5
• 化学式: C₉H₁₀ClNO₃S
• 分子量: 247.702
• InChiKey: LBWWWMBGRDDZMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  94.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-Chloracetyl-β-2-thienyl-DL-β-alanin 在 CoCl₂ porcine kidney acylase I 作用下， 以 phosphate buffer 为溶剂， 反应 45.0h， 生成 (S)-3-amino-3-(2-thienyl)propanoic acid
  参考文献：
  名称：

  The first aminoacylase-catalyzed enantioselective synthesis of aromatic β-amino acids

  摘要：

  报道了第一个氨酰化酶催化的芳香族β-氨基酸的对映选择性合成。底物中存在 N-氯乙酰基作为酰基以及使用猪肾酰基转移酶 I 作为合适的酶成分是此解析过程的先决条件，由此形成具有 >98 的高对映选择性的光学活性 β-氨基酸% ee。

  DOI：

  10.1039/b406380e

文献信息

• Process for preparing optically active beta-aminocarboxylic acids from racemic n-acylated beta-aminocarboxylic acids
  申请人：Groger Harald

  公开号：US20050153401A1

  公开（公告）日：2005-07-14

  A process is described for preparing optically active β-atninocarboxylic acids from racemic N-acylated β-aminocarboxylic acids by cnantiosclccthc hydrolysis of the N-acylated β-aminocarboxylic acid in the presence of a hydrolase by way of biocatalyst, wherein the N-acyl substituent of the N-acylated β-aminocarboxylic acid (I) exhibits Structure I in which R 1 , R 2 are each selected, independently of one another, from H, halogen, alkiyl residues, OH, alkoxy residues and aryloxy residues; R 3 is selected from halogen, alkoxy residues and aryloxy residues; (II) Structure IIA or IIB or the structure of the corresponding salts or (III) Structure III or the structure of the corresponding salt.

  本文描述了一种制备光学活性β-氨基羧酸的过程，该过程通过生物催化剂中的水解酶，在N-酰化的β-氨基羧酸存在下进行对映选择性水解，其中N-酰基取代基（I）的结构为I结构，其中R1、R2分别独立地选择自H、卤素、烷基残基、OH、烷氧基和芳氧基；R3从卤素、烷氧基和芳氧基中选择；（II）IIA或IIB结构或相应盐的结构或（III）III结构或相应盐的结构。
• PROCESS FOR PREPARING OPTICALLY ACTIVE BETA-AMINOCARBOXYLIC ACIDS FROM RACEMIC N-ACYLATED BETA-AMINOCARBOXYLIC ACIDS
  申请人：Degussa AG

  公开号：EP1487990A2

  公开（公告）日：2004-12-22
• [EN] PROCESS FOR PREPARING OPTICALLY ACTIVE BETA-AMINOCARBOXYLIC ACIDS FROM RACEMIC N-ACYLATED BETA-AMINOCARBOXYLIC ACIDS<br/>[FR] PROCEDE DE PREPARATION D'ACIDES BETA-AMINOCARBOXYLIQUES OPTIQUEMENT ACTIFS A PARTIR D'ACIDES BETA-AMINOCARBOXYLIQUES N-ACYLES RACEMIQUES
  申请人：DEGUSSA

  公开号：WO2003080854A2

  公开（公告）日：2003-10-02

  A process is described for preparing optically active β-aminocarboxylic acids from racemic N-acylated β-aminocarboxylic acids by enantioselective hydrolysis of the N-acylated β-aminocarboxylic acid in the presence of a hydrolase by way of biocatalyst, wherein the N-acyl substituent of the N-acylated β-aminocarboxylic acid (I) exhibits Structure I in which R1, R2 are each selected, independently of one another, from H, halogen, alkyl residues, OH, alkoxy residues and aryloxy residues; R3 is selected from halogen, alkoxy residues and aryloxy residues; (II) Structure IIA or IIB or the structure of the corresponding salts or (III) Structure III or the structure of the corresponding salt.
• The first aminoacylase-catalyzed enantioselective synthesis of aromatic β-amino acids
  作者：Harald Gröger、Harald Trauthwein、Stefan Buchholz、Karlheinz Drauz、Christiane Sacherer、Sylvie Godfrin、Helge Werner

  DOI：10.1039/b406380e

  日期：——

  The first aminoacylase-catalyzed enantioselective synthesis of aromatic β-amino acids is reported. The presence of an N-chloroacetyl group as acyl group in the substrate as well as the use of porcine kidney acylase I as a suitable enzyme component are prerequisites for this resolution process whereby optically active β-amino acids are formed with high enantioselectivities of >98% ee.

  报道了第一个氨酰化酶催化的芳香族β-氨基酸的对映选择性合成。底物中存在 N-氯乙酰基作为酰基以及使用猪肾酰基转移酶 I 作为合适的酶成分是此解析过程的先决条件，由此形成具有 >98 的高对映选择性的光学活性 β-氨基酸% ee。