(3R)-3-hydroxy-3-phenylpropanethioamide | 1170316-54-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3R)-3-hydroxy-3-phenylpropanethioamide
• CAS: 1170316-54-7
• 化学式: C₉H₁₁NOS
• 分子量: 181.258
• InChiKey: YZKXPGXDJBSKSC-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  46.25
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  glucosibarin 在 iron(II) sulfate 作用下， 以 phosphate buffer 、 acetate buffer 为溶剂， 反应 24.0h， 生成 1-吖丁啶羧酸,3-[(2-溴苯基)磺酰]-,1,1-二甲基乙基酯 、 (3R)-3-hydroxy-3-phenylpropanethioamide 、 (R)-3-phenyl-3-hydroxypropanenitrile
  参考文献：
  名称：

  Fe²⁺-Catalyzed Formation of Nitriles and Thionamides from Intact Glucosinolates

  摘要：

  The ratio of isothiocyanates to nitriles formed upon the hydrolysis of glucosinolates is a key factor determining the physiological effect of glucosinolate-containing plants and materials. A micellar electrokinetic capillary chromatography (MECC) method was used to study the nonenzymatic Fe2+-catalyzed transformation of glucosinolates. At room temperature, pH 5, and in the presence of only 2 molar excess of Fe2+ all glucosinolate was degraded in 24 h. At all molar excess Fe2+ tested, nitriles were the major compounds formed. Thionamides were also formed from glucosinolates that contained a side chain hydroxylated at C-2; in this case, trace amounts of oxazolidine-2-thione were also detected. The presence of Fe3+ had no effect. The nonenzymatic Fe2+-catalyzed transformation of glucosinolates involves the binding of Fe2+ to the glucosinolate to form a complex.

  DOI：

  10.1021/np070438d