(4S)-4-hydroxy-2-phenylsulfanylpentanoic acid | 288585-37-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (4S)-4-hydroxy-2-phenylsulfanylpentanoic acid
• CAS: 288585-37-5
• 化学式: C₁₁H₁₄O₃S
• 分子量: 226.296
• InChiKey: LOVVOPCMUVPDNW-PEHGTWAWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  82.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S)-4-hydroxy-2-phenylsulfanylpentanoic acid 在 Raney-Ni (W₆) 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以78%的产率得到(S)-γ-valerolactone
  参考文献：
  名称：

  The absolute configuration of (-)-botryococcene

  摘要：

  DOI：

  10.1021/ja00277a054
• 作为产物：
  描述：

  苯硫基乙酸 、 S-环氧丙烷 在 lithium diisopropyl amide 作用下， 生成 (4S)-4-hydroxy-2-phenylsulfanylpentanoic acid
  参考文献：
  名称：

  Degradation and absolute configurational assignment to C34-botryococcene

  摘要：

  C34-Botryococcene, the major hydrocarbon constituent of the B race of Botryoeoccus braunii, was degraded by ozonolysis of its dihydro derivative followed by Baeyer-Villiger oxidation to gamma-valerolactone, 2,5-dimethylhexanolactone, and 2-ethyl-2,5-dimethylhexanolactone. These three lactones were correlated with enantiomerically pure, synthesized materials using a progressive induced chemical shift technique with the chiral shift reagent Eu(hfc)3. The lactones were found to possess 4S, 2R,5S, and 2R,5S configurations respectively, thereby specifying a 3S,7S,10R,13S,16S,20S configuration for C34-botryococcene. A biogenesis for botryococcene from 1R,2R,3R presqualene diphosphate is proposed to account for the observed 10R,13S configuration.

  DOI：

  10.1021/jo00044a039

文献信息

• The absolute configuration of (-)-botryococcene
  作者：James D. White、Todd C. Somers、G. Nagabushana. Reddy

  DOI：10.1021/ja00277a054

  日期：1986.8
• Total Synthesis of Muconin by Efficient Assembly of Chiral Building Blocks
  作者：Scott E. Schaus、Jonas Brånalt、Eric N. Jacobsen

  DOI：10.1021/jo9810765

  日期：1998.7.1
• Degradation and absolute configurational assignment to C34-botryococcene
  作者：James D. White、Todd C. Somers、G. Nagabushana Reddy

  DOI：10.1021/jo00044a039

  日期：1992.8

  C34-Botryococcene, the major hydrocarbon constituent of the B race of Botryoeoccus braunii, was degraded by ozonolysis of its dihydro derivative followed by Baeyer-Villiger oxidation to gamma-valerolactone, 2,5-dimethylhexanolactone, and 2-ethyl-2,5-dimethylhexanolactone. These three lactones were correlated with enantiomerically pure, synthesized materials using a progressive induced chemical shift technique with the chiral shift reagent Eu(hfc)3. The lactones were found to possess 4S, 2R,5S, and 2R,5S configurations respectively, thereby specifying a 3S,7S,10R,13S,16S,20S configuration for C34-botryococcene. A biogenesis for botryococcene from 1R,2R,3R presqualene diphosphate is proposed to account for the observed 10R,13S configuration.