(S)-3-methylpentanethioic acid S-phenyl ester | 725240-13-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯硫酚酯
• 英文名称: (S)-3-methylpentanethioic acid S-phenyl ester
• 英文别名: (3S)-methylpentanethioic acid S-phenylester；S-phenyl (3S)-3-methylpentanethioate
• CAS: 725240-13-1
• 化学式: C₁₂H₁₆OS
• 分子量: 208.324
• InChiKey: WCYWJXUQZXHOHM-JTQLQIEISA-N

物化性质

• 沸点：
  90-95 °C(Press: 0.4 Torr)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-3-methylpentanethioic acid S-phenyl ester 在 2,2,6,6-四甲基哌啶 、 tin(II) trifluoromethanesulfonate 、 正丁基锂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 53.0h， 生成 (2R,3S,4S)-2-hydroxy-4-methyl-3-phenylsulfanylcarbonylhexanoic acid
  参考文献：
  名称：

  Enantioselective Total Syntheses of Belactosin A, Belactosin C, and Its Homoanalogue

  摘要：

  Enantioselective total syntheses of belactosin A, belactosin C, and its homoanalogue have been accomplished in high overall yields (32% for belactosin A from the amino acid 10, and 35 and 36% for belactosin C and its homoanalogue, respectively). This concise approach comprises a novel sequential acylation/beta-lactonization reaction and allows a facile alteration of the substituents, thus providing a flexible route to a new family of highly active belactosin-based proteasome inhibitors.

  DOI：

  10.1021/ol049409+
• 作为产物：
  描述：

  L-异亮氨酸 在 4-二甲氨基吡啶 、 sodium hydroxide 、 N,N'-二环己基碳二亚胺 、 hydroxylamine-O-sulfonic acid 作用下， 以 二氯甲烷 为溶剂， 反应 28.0h， 生成 (S)-3-methylpentanethioic acid S-phenyl ester
  参考文献：
  名称：

  Enantioselective Total Syntheses of Belactosin A, Belactosin C, and Its Homoanalogue

  摘要：

  Enantioselective total syntheses of belactosin A, belactosin C, and its homoanalogue have been accomplished in high overall yields (32% for belactosin A from the amino acid 10, and 35 and 36% for belactosin C and its homoanalogue, respectively). This concise approach comprises a novel sequential acylation/beta-lactonization reaction and allows a facile alteration of the substituents, thus providing a flexible route to a new family of highly active belactosin-based proteasome inhibitors.

  DOI：

  10.1021/ol049409+

文献信息

• Synthesis and biological activity of simplified belactosin C analogues
  作者：Armin de Meijere、Vadim S. Korotkov、Alexander V. Lygin、Oleg V. Larionov、Viktor V. Sokolov、Tine Graef、Mazen Es-Sayed

  DOI：10.1039/c2ob25586c

  日期：——

  Successful biochemical studies of the natural products belactosin A and C and their acylated congeners have shown a β-lactonecarboxamide moiety to be a possible core structure of powerful proteasome inhibitors. As a part of further investigations, variously decorated simplified β-lactonecarboxamides have been synthesized in order to understand structure–biological activity relations in detail, to find ways of improving their biological activity and stability and to reduce the complexity of their preparation. Biological tests showed that the best compounds possess a high potential against phytopathogenic fungi in the greenhouse.

  对天然产物贝拉糖苷 A 和 C 及其酰化同系物的成功生化研究表明，β-内酯羧酰胺分子可能是强力蛋白酶体抑制剂的核心结构。作为进一步研究的一部分，我们合成了各种装饰简化的 β-内酯羧酰胺，以详细了解结构-生物活性关系，找到提高其生物活性和稳定性的方法，并降低其制备的复杂性。生物测试表明，最佳化合物对温室中的植物病原真菌具有很高的抗病潜力。
• Enantioselective Total Syntheses of Belactosin A, Belactosin C, and Its Homoanalogue
  作者：Oleg V. Larionov、Armin de Meijere

  DOI：10.1021/ol049409+

  日期：2004.6.1

  Enantioselective total syntheses of belactosin A, belactosin C, and its homoanalogue have been accomplished in high overall yields (32% for belactosin A from the amino acid 10, and 35 and 36% for belactosin C and its homoanalogue, respectively). This concise approach comprises a novel sequential acylation/beta-lactonization reaction and allows a facile alteration of the substituents, thus providing a flexible route to a new family of highly active belactosin-based proteasome inhibitors.