N-Thiobenzoyl-L-leucin | 2584-82-9

• 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-Thiobenzoyl-L-leucin
• CAS: 2584-82-9
• 化学式: C₁₃H₁₇NO₂S
• 分子量: 251.349
• InChiKey: SEZKYZIKGVYKQI-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.45
• 重原子数：
  17.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  49.33
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-Thiobenzoyl-L-leucin 生成 N-benzoyl-L-leucine 4-isobutyl-2-phenyl-thiazol-5-yl ester
  参考文献：
  名称：

  N-硫代苯甲酰基-α-氨基酸及相关的N-取代的硫代苯甲酰胺与三氟乙酸酐的反应

  摘要：

  通过N-硫代苯甲酰基-α-氨基酸与三氟乙酸酐的反应形成5-（2'-苯甲酰酰氧基）噻唑。经过类似处理的相应酯经过等位SO交换，得到N-苯甲酰基-α-氨基酸酯。虽然这些是在N-（2-羧基）的反应所示的差异进一步的例子thiobenzamides与他们的苯甲酰胺类似物，N进行比较α发现-硫代苯甲酰基-α-氨基酸酰胺在三氟乙酸酐中进行环化反应，生成5-三氟乙酰氨基-噻唑，遵循与它们的N-苯甲酰基类似物相同的反应路径。末端N-硫代苯甲酰基二肽经三氟乙酸酐处理后可生成5-（N-2-羧基烷基）三氟乙酰氨基-噻唑，并且确定三氟乙酸酐不能裂解末端N-硫代酰基二肽的酰胺基，因此不适合使用用于多肽的埃德曼型序列分析的试剂。

  DOI：

  10.1016/0040-4020(78)80062-3
• 作为产物：
  描述：

  4-isobutyl-2-phenyl-4H-thiazol-5-one 以 乙腈 为溶剂， 反应 88.0h， 以78%的产率得到N-Thiobenzoyl-L-leucin
  参考文献：
  名称：

  Enzymic asymmetric synthesis of .alpha.-amino acids. Enantioselective cleavage of 4-substituted oxazolin-5-ones and thiazolin-5-ones

  摘要：

  A general enzymatic asymmetric synthesis of L-alpha-amino acids has been developed. This method entails the use of the Pseudomonas cepacia lipase (P-30) to catalyze the enantioselective methanolysis of a variety of 4-substituted 2-phenyloxazolin-5-one derivatives in a nonpolar organic solvent to furnish optically-active N-benzoyl-L-alpha-amino acid methyl esters (ee = 66-98%), which in turn is subjected to a protease-catalyzed kinetic resolution yielding enantiomerically-pure N-benzoyl-L-alpha-amino acids. This synergistic coupling of two enzymes allows the ready preparation of L-alpha-amino acids of high enantiopurity in yields greater than 50%, an inherent advantage over conventional resolution procedures. Two proteases were found to catalyze the enantioselective hydrolysis of a variety of 4-substituted 2-phenylthiazolin-5-one derivatives to give N-(thiobenzoyl)-L-alpha-amino acids of high optical purity.

  DOI：

  10.1021/jo00064a010

文献信息

• Efficient solid-phase synthesis of 4,5-dihydro-1,2,4-triazin-6(1H)-ones
  作者：Damien Boeglin、Sonia Cantel、Jean Martinez、Jean-Alain Fehrentz

  DOI：10.1016/s0040-4039(02)02591-1

  日期：2003.1

  A new and easy protocol for the formation of substituted 4,5-dihydro-1,2,4-triazin-6(1H)-ones was developed on solid support. The heterocyclic compounds were formed by nucleophilic reaction of hydrazine on thioamide esters. As cyclization was concomitant with cleavage from the support, substituted 4,5-dihydrotriazinones were obtained in high purity. (C) 2002 Elsevier Science Ltd. All rights reserved.