(5R)-3-[(S)-13-hydroxy-13-((S)-5-oxotetrahydrofuran-2-yl)tridec-6-en-8-ynyl]-5-methyl-3-(phenylsulfanyl)dihydrofuran-2-one | 628687-62-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (5R)-3-[(S)-13-hydroxy-13-((S)-5-oxotetrahydrofuran-2-yl)tridec-6-en-8-ynyl]-5-methyl-3-(phenylsulfanyl)dihydrofuran-2-one
• CAS: 628687-62-7
• 化学式: C₂₈H₃₆O₅S
• 分子量: 484.657
• InChiKey: REUIQHRWYYLYBU-WMUBDEIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  34.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  72.83
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (5R)-3-[(S)-13-hydroxy-13-((S)-5-oxotetrahydrofuran-2-yl)tridec-6-en-8-ynyl]-5-methyl-3-(phenylsulfanyl)dihydrofuran-2-one 在 RhCl(PPh₃)3 、 氢气 作用下， 以 甲醇 、 苯 为溶剂， 反应 24.0h， 以87%的产率得到(5R)-3-[(S)-13-hydroxy-13-((S)-5-oxotetrahydrofuran-2-yl)tridecyl]-5-methyl-3-(phenylsulfanyl)dihydrofuran-2-one
  参考文献：
  名称：

  Synthesis of (15S,16S,21R)-4-deoxyrollicosin analog

  摘要：

  Synthesis of 4-deoxy rollicosin analog 2 was completed in nine steps, which was based on palladium-catalyzed coupling of two building blocks 3 and 4. Lactone 3 was synthesized from 5-hexyn-1-ol, and vinyl iodide 4 was accessed from L-glutamate and 1-hexyne. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.08.088
• 作为产物：
  描述：

  (R)-5-methyl-3-phenylthio-3H-dihydrofuran-2-one 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 26.5h， 生成 (5R)-3-[(S)-13-hydroxy-13-((S)-5-oxotetrahydrofuran-2-yl)tridec-6-en-8-ynyl]-5-methyl-3-(phenylsulfanyl)dihydrofuran-2-one
  参考文献：
  名称：

  Design, syntheses, and biological evaluations of squamostolide and its related analogs

  摘要：

  Squamostolide and its related analogs were designed and synthesized for biological evaluation. All these compounds were tested for growth inhibition activities against human tumor cell lines, in which one of the compounds showed the most potent cyto-toxicity among these derivatives against a full panel of 60 human cancer cell lines. The same compound also showed G2/M phase arrest and a weak apoptotic effect during flow cytometric analysis. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.05.050