(-)-homomethionine | 108691-69-6

• 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: (-)-homomethionine
• 英文别名: (R)-2-amino-5-(methylthio)pentanoic acid；D-homomethionine；(2R)-2-amino-5-methylsulfanylpentanoic acid
• CAS: 108691-69-6
• 化学式: C₆H₁₃NO₂S
• 分子量: 163.241
• InChiKey: SFSJZXMDTNDWIX-RXMQYKEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  (-)-homomethionine 生成 (R)-2-Ethylsulfanylthiocarbonylamino-5-methylsulfanyl-pentanoic acid
  参考文献：
  名称：

  Resolution of 2-amino-5-thiomethyl pentanoic acid (homomethionine) with aminopeptidase from or chiral phosphoric acids.

  摘要：

  DOI：

  10.1016/s0040-4039(00)84445-7
• 作为产物：
  描述：

  (R)-5-Methylsulfanyl-2-{[1-phenyl-meth-(E)-ylidene]-amino}-pentanoic acid amide 在 硫酸 作用下， 以 水 为溶剂， 以68%的产率得到(-)-homomethionine
  参考文献：
  名称：

  Resolution of 2-amino-5-thiomethyl pentanoic acid (homomethionine) with aminopeptidase from or chiral phosphoric acids.

  摘要：

  DOI：

  10.1016/s0040-4039(00)84445-7

文献信息

• A Practical and Efficient Green Synthesis of β-Aminophosphoryl Compounds via the Aza-Michael Reaction in Water
  作者：Ekaterina V. Matveeva、Anatoly E. Shipov、Irina L. Odinets

  DOI：10.1080/10426507.2010.511358

  日期：2011.3.31

  as a solvent (without any cosolvent) promotes the aza-Michael reaction of diethyl vinylphosphonate and diphenylvinylphosphine oxide with a wide range of N-nucleophiles. The solubility of the starting phosphorus substrate in water does not play a crucial role in the reaction course, decreasing to some extent the reaction rate. The reaction can be performed either at room temperature or under reflux to

  摘要 使用水作为溶剂（没有任何助溶剂）促进了乙烯基膦酸二乙酯和二苯基乙烯基氧化膦与多种 N-亲核试剂的氮杂-迈克尔反应。起始磷底物在水中的溶解度在反应过程中不起关键作用，在一定程度上降低了反应速率。该反应可以在室温或回流下进行，以通过简单的冷冻干燥分离程序以优异的产率和高纯度提供相应的 β-氨基膦酸酯和 β-氨基膦氧化物。碱性催化剂的应用使得弱亲核试剂如α-氨基酸及其磷类似物的添加成为可能；即α-氨基膦酸。
• 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.
• Design of ligands derived from sulfur containing amino acids for enantioselective cross coupling catalyzed by nickel. Intramolecular participation of sulfide
  作者：Bindert K Vriesema、Richard M Kellogg

  DOI：10.1016/s0040-4039(00)84446-9

  日期：1986.1
• Resolution of 2-amino-5-thiomethyl pentanoic acid (homomethionine) with aminopeptidase from or chiral phosphoric acids.
  作者：B.K Vriesema、H ten Hoeve、H Wynberg、Richard M Kellogg、W.H.J Boesten、E.M Meijer、H.E Schoemaker

  DOI：10.1016/s0040-4039(00)84445-7

  日期：1986.1