2-methyl-5-(2-methylbut-3-en-2-yl)-2-vinyltetrahydrofuran

• 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-methyl-5-(2-methylbut-3-en-2-yl)-2-vinyltetrahydrofuran
• 英文别名: (2S,5R)-2-ethenyl-2-methyl-5-(2-methylbut-3-en-2-yl)oxolane
• 化学式: C₁₂H₂₀O
• 分子量: 180.29
• InChiKey: ZJNZGBOEEGMIIC-ZYHUDNBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (E)-6-acetoxy-4-methyl-4-hexenal 在 lithium aluminium tetrahydride 、 正丁基锂 、 三氟甲磺酸 、 二异丙胺 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 10.17h， 生成 2-methyl-5-(2-methylbut-3-en-2-yl)-2-vinyltetrahydrofuran
  参考文献：
  名称：

  Synthesis and olfactory properties of unnatural derivatives of lilac aldehydes

  摘要：

  Lilac aldehydes are considered as principal olfactory molecules of lilac flowers. We have designed, prepared and evaluated two sets of their unnatural racemic analogues as pure diastereomers. While the synthesis of gem-dimethyl homologues starts from geranyl acetate, the preparation of methylene derivatives commences from linalyl acetate. The key Lewis and/or Bronsted acid catalysed cyclisation furnishes easily separable cis-/trans-tetrahydrofuranyl esters as common advanced intermediates. The subsequent functional group transformations lead to target aldehydes, alcohols, nitriles and olefins. Unlike the homologues possessing similar herbal scents, methylene derivatives exhibit woody and/or flowery odours. In the latter case, the sensory evaluation suggests the importance of relative stereochemistry and/or type of functional group on the odour character of respective compounds. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.07.030

文献信息

• Synthesis and olfactory properties of unnatural derivatives of lilac aldehydes
  作者：Peter Šiška、Peter Fodran、Peter Szolcsányi

  DOI：10.1016/j.tet.2014.07.030

  日期：2014.9

  Lilac aldehydes are considered as principal olfactory molecules of lilac flowers. We have designed, prepared and evaluated two sets of their unnatural racemic analogues as pure diastereomers. While the synthesis of gem-dimethyl homologues starts from geranyl acetate, the preparation of methylene derivatives commences from linalyl acetate. The key Lewis and/or Bronsted acid catalysed cyclisation furnishes easily separable cis-/trans-tetrahydrofuranyl esters as common advanced intermediates. The subsequent functional group transformations lead to target aldehydes, alcohols, nitriles and olefins. Unlike the homologues possessing similar herbal scents, methylene derivatives exhibit woody and/or flowery odours. In the latter case, the sensory evaluation suggests the importance of relative stereochemistry and/or type of functional group on the odour character of respective compounds. (C) 2014 Elsevier Ltd. All rights reserved.