2-(2-butenylidene)-3,3-dimethyl-5-(2-oxopropyl)tetrahydrofuran

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: 2-(2-butenylidene)-3,3-dimethyl-5-(2-oxopropyl)tetrahydrofuran
• 英文别名: 2-(2-Butenylidene)-3,3-dimethyl-5-(2-oxopropyl)tetrahydrofuran, diastereomer 1；1-[(5E)-5-[(E)-but-2-enylidene]-4,4-dimethyloxolan-2-yl]propan-2-one
• 化学式: C₁₃H₂₀O₂
• 分子量: 208.301
• InChiKey: SUQDFKVIGVYZSR-DVIJZSFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-hydroxy-β-ionol 在 水 、 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 2-(2-butenylidene)-3,3-dimethyl-5-(2-oxopropyl)tetrahydrofuran
  参考文献：
  名称：

  2-(2-Butenylidene)-3,3-dimethyl-5-(2-oxopropyl)tetrahydrofuran: A New Degradation Product of 3-Hydroxy-5,6-epoxy-.beta.-ionol

  摘要：

  Identification of 2-(2-butenylidene)-3,3-dimethyl-5-(2-oxopropyl)tetrahydrofuran diastereomers (4, 5) in various leaves [stinging nettle; sloe tree; strawberry; vine (Riesling); sweet silique (Bunias orientalis)] was achieved by comparison of HRGC retention and spectral (MS; vapor phase FTIR) data with those of synthetic references. Model experiments revealed their acid-catalyzed formation from 3-hydroxy-5,6-epoxy-beta-ionol that was present in glycosidically bound form in the above-mentioned leaves. Assignment of the isomers 4a/4b and 5a/5b was established by NOE experiments. Enantiodifferentiation carried out by on-line coupled multidimensional gas chromatography-mass spectrometry revealed the occurrence of enantiomerically pure 5S enantiomers 4b/5b in the natural sources. A pathway for the selective formation of 4b/5b in nature is proposed.

  DOI：

  10.1021/jf00048a044

文献信息

• 2-(2-Butenylidene)-3,3-dimethyl-5-(2-oxopropyl)tetrahydrofuran: A New Degradation Product of 3-Hydroxy-5,6-epoxy-.beta.-ionol
  作者：Wolfgang Neugebauer、Peter Winterhalter、Peter Schreier

  DOI：10.1021/jf00048a044

  日期：1994.12

  Identification of 2-(2-butenylidene)-3,3-dimethyl-5-(2-oxopropyl)tetrahydrofuran diastereomers (4, 5) in various leaves [stinging nettle; sloe tree; strawberry; vine (Riesling); sweet silique (Bunias orientalis)] was achieved by comparison of HRGC retention and spectral (MS; vapor phase FTIR) data with those of synthetic references. Model experiments revealed their acid-catalyzed formation from 3-hydroxy-5,6-epoxy-beta-ionol that was present in glycosidically bound form in the above-mentioned leaves. Assignment of the isomers 4a/4b and 5a/5b was established by NOE experiments. Enantiodifferentiation carried out by on-line coupled multidimensional gas chromatography-mass spectrometry revealed the occurrence of enantiomerically pure 5S enantiomers 4b/5b in the natural sources. A pathway for the selective formation of 4b/5b in nature is proposed.