(S)-9-((5S)-2-oxo-tetrahydrofuran-5-yl)-non-1-en-3-ol | 1268624-49-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-9-((5S)-2-oxo-tetrahydrofuran-5-yl)-non-1-en-3-ol
• 英文别名: (5S)-5-[(7S)-7-hydroxynon-8-enyl]oxolan-2-one
• CAS: 1268624-49-2
• 化学式: C₁₃H₂₂O₃
• 分子量: 226.316
• InChiKey: DOORIIFWWJQWKH-NEPJUHHUSA-N

物化性质

• 沸点：
  376.6±15.0 °C(Predicted)
• 密度：
  1.017±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  8
• 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：

  (S)-9-((5S)-2-oxo-tetrahydrofuran-5-yl)-non-1-en-3-ol 在 詹氏催化剂 、 dimethyl sulfide borane 、 碳酸氢钠 、 戴斯-马丁氧化剂 、 (R)-2-甲基-CBS-恶唑硼烷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 26.5h， 生成 (8R,6E)-14-((5S)-2-oxo-tetrahydrofuran-5-yl)-tetradec-6-en-8-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)-Decane-1,2,9,10-tetraol 在 正丁基锂 、 水 、 sodium methylate 、 二正丁基氧化锡 、 potassium carbonate 、 三乙胺 、 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 20.08h， 生成 (S)-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

文献信息

• Synthesis of the structures proposed for natural butanolides piliferolides A and C
  作者：Jing Guan、Zhi-Bin Zhen、Yang Zou、Zheng-Yu Yue、Ping Jiang、Yan Li、Yikang Wu

  DOI：10.1016/j.tet.2010.12.037

  日期：2011.2

  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.