2-amino-5-<(phenylmethyl)thio>pentanoic acid | 144084-04-8

• 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: 2-amino-5-<(phenylmethyl)thio>pentanoic acid
• 英文别名: 2-amino-5-benzylsulfanyl-valeric acid；2-Amino-5-benzylmercapto-valeriansaeure；2-Amino-5-benzylsulfanylpentanoic acid
• CAS: 144084-04-8
• 化学式: C₁₂H₁₇NO₂S
• 分子量: 239.338
• InChiKey: URHYOXZEINUHIQ-UHFFFAOYSA-N

物化性质

• 熔点：
  222-224 °C(Solv: water (7732-18-5))
• 沸点：
  402.0±45.0 °C(Predicted)
• 密度：
  1.191±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  88.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-amino-5-<(phenylmethyl)thio>pentanoic acid 在 sodium 、 正丁醇 作用下， 生成 2,2'-diamino-5,5'-disulfanediyl-di-valeric acid
  参考文献：
  名称：

  Gaudry et al., 1952, vol. 11, p. 132,138

  摘要：

  DOI：
• 作为产物：
  描述：

  2,2'-diamino-5,5'-disulfanediyl-di-valeric acid 在 氨 、 sodium 作用下， 生成 2-amino-5-<(phenylmethyl)thio>pentanoic acid
  参考文献：
  名称：

  du Vigneaud et al., Journal of Biological Chemistry, 1934, vol. 106, p. 401,405

  摘要：

  DOI：

文献信息

• [EN] PROCESS FOR PRODUCING SULFUR-CONTAINING AMINO ACID OR SALT THEREOF<br/>[FR] PROCÉDÉ DE PRODUCTION D'UN ACIDE AMINÉ CONTENANT DU SOUFRE OU DE L'UN DE SES SELS
  申请人：SUMITOMO CHEMICAL CO

  公开号：WO2011118849A1

  公开（公告）日：2011-09-29

  According to the present invention, a new process for producing a sulfur-containing amino acid without using of hydrogen cyanide or sodium azide which requires careful handling as a raw material can be provided. The present invention relates to a process for producing a sulfur-containing amino acid represented by the following formula (1) or a salt thereof: wherein R1 is an alkyl group having 1 to 12 carbon atoms and optionally having substituents or a cycloalkyl group having 3 to 12 carbon atoms and optionally having substituents, and n is an integral number of from 1 to 4, comprising a step of reacting a sulfur-containing 2-ketocarboxylic acid represented by the formula (2) or a salt thereof: wherein R1 and n mean the same as defined above, with ammonia and hydrogen in the presence of a transition metal catalyst.

  根据本发明，可以提供一种新的生产含硫氨基酸的方法，而不需要使用需要小心处理的氢氰酸或偏氮化钠作为原料。本发明涉及一种生产以下式（1）或其盐所表示的含硫氨基酸的方法：其中R1是具有1至12个碳原子并可选择具有取代基的烷基或具有3至12个碳原子并可选择具有取代基的环烷基，n是从1至4的整数，包括以下步骤：在过渡金属催化剂的存在下，将以下式（2）或其盐所表示的含硫2-酮羧酸与氨和氢反应。其中R1和n的含义如上所定义。
• Synthesis of (optically active) sulfur-containing trifunctional amino acids by radical addition to (optically active) unsaturated amino acids
  作者：Quirinus B. Broxterman、Bernard Kaptein、Johan Kamphuis、Hans E. Schoemaker

  DOI：10.1021/jo00049a041

  日期：1992.11

  Sulfur-based radicals, generated from R-S-H-type precursors (R = alkyl, acyl) with AIBN, smoothly add to alpha-allylglycines protected at none, one, or both of the amino acid functions (NH2 and/or CO2H). Sulfur-containing trifunctional amino acids were obtained in good to excellent yields (64-100%). The solvent used for the reaction is critical. Optimal results were obtained when both the unsaturated amino acid and RSH dissolve completely in the medium (dioxane/water or methanol/water are good solvent systems). The scope of the reaction includes alpha-substituted alpha-allylglycine and derivatives as well as beta-substituted beta-allyl-beta-ammo alcohols. In the case of optically active alpha-allylglycine derivatives, radical addition is accompanied by a small amount of racemization, the amount depending on the type of protection and R-S-H. The products are easily optically enriched by crystallization. Addition of sulfur-based radicals to alpha-allylglycine is believed to be an example of a general method for synthesizing optically active trifunctional amino acids from unsaturated amino acids.
• PROCESS FOR PRODUCING SULFUR-CONTAINING AMINO ACID OR SALT THEREOF
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP2550251B1

  公开（公告）日：2015-04-29
• US8779190B2
  申请人：——

  公开号：US8779190B2

  公开（公告）日：2014-07-15