(2S*,3R*,6S*)-3-(α-ethoxybenzyl)-2-methyltetrahydrofuran

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S*,3R*,6S*)-3-(α-ethoxybenzyl)-2-methyltetrahydrofuran
• 英文别名: (2S,3R)-3-[(S)-ethoxy(phenyl)methyl]-2-methyloxolane
• 化学式: C₁₄H₂₀O₂
• 分子量: 220.312
• InChiKey: ABTGDDKBCIRCLB-IACUBPJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯甲醛二乙缩醛 在 对甲苯磺酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 40.0h， 生成 (2S*,3R*,6S*)-3-(α-ethoxybenzyl)-2-methyltetrahydrofuran
  参考文献：
  名称：

  Additions of 1-(.alpha.-alkoxybenzyl)benzotriazoles to enol ethers. New routes to 1,3-diethers

  摘要：

  1-(alpha-Alkoxybenzyl)benzotriazoles undergo reversible ionization in solution to a benzotriazolyl anion (Bt-) and carboxonium cations PhCH:O+R. These cations can attack the beta-carbon atom of enol ethers to give cation adducts which add the Bt- to form new alpha-(benzotriazol-1-yl)alkyl ethers in which the carbon chains are extended by an alpha-ethoxybenzyl group. Reactions of these adducts with Grignard reagents produce the corresponding 1,3-diethers in high yield. Reduction of the adducts with lithium aluminum hydride gives the corresponding diethers via substitution of the benzotriazolyl moiety with a hydrogen atom or 1-(3-alkoxyalkyl)benzotriazoles via substitution of the alpha-alkoxy group, depending on the reaction conditions and the nature of the adduct.

  DOI：

  10.1021/jo00044a030

文献信息

• Additions of 1-(.alpha.-alkoxybenzyl)benzotriazoles to enol ethers. New routes to 1,3-diethers
  作者：Alan R. Katritzky、Stanislaw Rachwal、Bogumila Rachwal、Peter J. Steel

  DOI：10.1021/jo00044a030

  日期：1992.8

  1-(alpha-Alkoxybenzyl)benzotriazoles undergo reversible ionization in solution to a benzotriazolyl anion (Bt-) and carboxonium cations PhCH:O+R. These cations can attack the beta-carbon atom of enol ethers to give cation adducts which add the Bt- to form new alpha-(benzotriazol-1-yl)alkyl ethers in which the carbon chains are extended by an alpha-ethoxybenzyl group. Reactions of these adducts with Grignard reagents produce the corresponding 1,3-diethers in high yield. Reduction of the adducts with lithium aluminum hydride gives the corresponding diethers via substitution of the benzotriazolyl moiety with a hydrogen atom or 1-(3-alkoxyalkyl)benzotriazoles via substitution of the alpha-alkoxy group, depending on the reaction conditions and the nature of the adduct.