5S-(1S-hydroxy-6-trimethylsilylhex-5-ynyl)dihydrofuran-2-one | 628687-59-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 5S-(1S-hydroxy-6-trimethylsilylhex-5-ynyl)dihydrofuran-2-one
• 英文别名: (5S)-5-[(1S)-1-hydroxy-6-trimethylsilylhex-5-ynyl]oxolan-2-one
• CAS: 628687-59-2
• 化学式: C₁₃H₂₂O₃Si
• 分子量: 254.401
• InChiKey: SUZZMBAFRYRTDF-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5S-(1S-hydroxy-6-trimethylsilylhex-5-ynyl)dihydrofuran-2-one 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 29.0h， 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：

  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：

  6-三甲基硅烷基-己-5-炔-1-醇 在 AD-mix-α 、 甲基磺酰胺 、 丙酸 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 31.0h， 生成 5S-(1S-hydroxy-6-trimethylsilylhex-5-ynyl)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

文献信息

• Synthesis of (15S,16S,21R)-4-deoxyrollicosin analog
  作者：Jeng-Lin Lee、Chi-Fong Lin、Ling-Yu Hsieh、Wan-Ru Lin、Huey-Fen Chiu、Yang-Chang Wu、Kun-Sheng Wang、Ming-Jung Wu

  DOI：10.1016/j.tetlet.2003.08.088

  日期：2003.10

  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.
• Design, syntheses, and biological evaluations of squamostolide and its related analogs
  作者：Cheng-Lin Lee、Chi-Fong Lin、Wan-Ru Lin、Kun-Sheng Wang、Ya-her Chang、Shinne-Ren Lin、Yang-Chang Wu、Ming-Jung Wu

  DOI：10.1016/j.bmc.2005.05.050

  日期：2005.10

  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.