2-(diethoxymethyl)oct-1-ene | 924650-96-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(diethoxymethyl)oct-1-ene
• CAS: 924650-96-4
• 化学式: C₁₃H₂₆O₂
• 分子量: 214.348
• InChiKey: ZISVAQOKDCMGRG-UHFFFAOYSA-N

物化性质

• 沸点：
  121 °C(Press: 13 Torr)
• 密度：
  0.979 g/cm3(Temp: 22 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  3.91
• 重原子数：
  15.0
• 可旋转键数：
  10.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-(diethoxymethyl)oct-1-ene 在 蔗糖 Saccharomyces cerevisiae 、 citric monohydrate 、 碳酸氢铵 、 甲基磺酰氯 、 三乙胺 、 四丁基氯化铵 作用下， 以 乙醇 、 水 、 乙醚 、 苯 为溶剂， 反应 80.0h， 以3.48 g的产率得到(2R)-1-chloro-2-methyloctane
  参考文献：
  名称：

  The synthesis of the insect pheromone (2S,3R,7R)-3,7-dimethyltridec-2-yl acetate from racemic 3,4-dimethyl-γ-butyrolactone by diastereoselective chiral resolution

  摘要：

  The insect pheromone (2S,3R,7R)-3,7-dimethyltridec-2-yl acetate 1-Ac was prepared from diastereomerically enriched (2S*,3R*,7R)-1, which in turn was obtained by the coupling of racemic 3,4-dimethyl-gamma-butyrolactone with (7S)-2-methyloctyllithium, followed by a Wolff-Kishner reduction of the resulting ketone. Conversion of (2S*,3R*,7R)-1 to the corresponding alkyl hydrogen phthalate and diastereomer salt formation with (S)-PhCHMeNH2 provided after several crystallizations individual diastereomer, which was later transformed into target 1-Ac after hydrolysis and acylation. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2006.11.005
• 作为产物：
  描述：

  1-hexylcyclopropyl methanesulfonate 在 硝酸铵 、 碳酸氢钠 、 magnesium bromide 作用下， 以 乙醚 、 乙醇 、 二甲基亚砜 为溶剂， 反应 60.0h， 生成 2-(diethoxymethyl)oct-1-ene
  参考文献：
  名称：

  The synthesis of the insect pheromone (2S,3R,7R)-3,7-dimethyltridec-2-yl acetate from racemic 3,4-dimethyl-γ-butyrolactone by diastereoselective chiral resolution

  摘要：

  The insect pheromone (2S,3R,7R)-3,7-dimethyltridec-2-yl acetate 1-Ac was prepared from diastereomerically enriched (2S*,3R*,7R)-1, which in turn was obtained by the coupling of racemic 3,4-dimethyl-gamma-butyrolactone with (7S)-2-methyloctyllithium, followed by a Wolff-Kishner reduction of the resulting ketone. Conversion of (2S*,3R*,7R)-1 to the corresponding alkyl hydrogen phthalate and diastereomer salt formation with (S)-PhCHMeNH2 provided after several crystallizations individual diastereomer, which was later transformed into target 1-Ac after hydrolysis and acylation. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2006.11.005