(S)-9-((5S)-2-oxo-tetrahydrofuran-5-yl)-non-1-en-3-one | 1268624-61-8

• 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: (S)-9-((5S)-2-oxo-tetrahydrofuran-5-yl)-non-1-en-3-one
• CAS: 1268624-61-8
• 化学式: C₁₃H₂₀O₃
• 分子量: 224.3
• InChiKey: KEBSECCGILROBA-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.79
• 重原子数：
  16.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S)-9-((5S)-2-oxo-tetrahydrofuran-5-yl)-non-1-en-3-one 在 dimethyl sulfide borane 、 (R)-2-甲基-CBS-恶唑硼烷 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以96%的产率得到(R)-9-((5S)-2-oxo-tetrahydrofuran-5-yl)-non-1-en-3-ol
  参考文献：
  名称：

  Synthesis of the structures proposed for natural butanolides piliferolides A and C

  摘要：

  The structures proposed for natural butanolides piliferolides A and C have been synthesized. The allylic and lactone stereogenic centers in the target structures were derived from D-mannitol, while that near the side-chain terminal was taken from (R)-propylene oxide. The synthetic samples helped to reveal that a signal at around delta 2.0 ppm was missing in the H-1 NMR data listing for the structures proposed for natural piliferolides, whereas the delta 29.7 ppm signal in the C-13 NMR reported for the structure proposed for natural piliferolide C most likely stemmed from the impurities in the chromatography solvent. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.12.037
• 作为产物：
  描述：

  (2S,9S)-1,10-di-tosyloxy-decan-2,9-diol 在 正丁基锂 、 水 、 sodium methylate 、 碳酸氢钠 、 potassium carbonate 、 戴斯-马丁氧化剂 、 sodium chloride 作用下， 以 四氢呋喃 、 甲醇 、 hexanes 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 21.08h， 生成 (S)-9-((5S)-2-oxo-tetrahydrofuran-5-yl)-non-1-en-3-one
  参考文献：
  名称：

  Synthesis of the structures proposed for natural butanolides piliferolides A and C

  摘要：

  The structures proposed for natural butanolides piliferolides A and C have been synthesized. The allylic and lactone stereogenic centers in the target structures were derived from D-mannitol, while that near the side-chain terminal was taken from (R)-propylene oxide. The synthetic samples helped to reveal that a signal at around delta 2.0 ppm was missing in the H-1 NMR data listing for the structures proposed for natural piliferolides, whereas the delta 29.7 ppm signal in the C-13 NMR reported for the structure proposed for natural piliferolide C most likely stemmed from the impurities in the chromatography solvent. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.12.037