3-tert-butoxy-2-methoxytetrahydropyrane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 3-tert-butoxy-2-methoxytetrahydropyrane
• 英文别名: 2-Methoxy-3-[(2-methylpropan-2-yl)oxy]oxane
• 化学式: C₁₀H₂₀O₃
• 分子量: 188.267
• InChiKey: DALKQCAEFJIAAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 、 甲醇 、 tert-butyl hypofluorite 以 氯仿 为溶剂， 以15%的产率得到1-甲氧基萘
  参考文献：
  名称：

  tert-Butyl HypofluoriteAn Electrophilic tert-Butoxylation Agent

  摘要：

  tert-Butyl hypofluorite, t-BuOF, easily synthesized from t-BuOH and F-2, is a unique source of the novel electrophilic tert-butoxylium moiety t-BuO+. It was added to several benzylic double bonds to form vicinal fluoro-tert-butoxide derivatives. Not surprisingly, this bulky reagent is quite sensitive to steric hindrance. The process is electrophilic in nature, but since the reaction is relatively slow (20-60 min) formation of various radical species can take place, forming eventually several distinct byproducts. t-BuOF was also reacted with a number of enols, producing the corresponding alpha-tert-butoxy ketone derivatives in moderate to good yields. The best results were obtained with benzylic enol derivatives.

  DOI：

  10.1021/jo9723366

文献信息

• <i>tert</i>-Butyl HypofluoriteAn Electrophilic <i>tert</i>-Butoxylation Agent
  作者：Iris Ben-David、Eyal Mishani、Shlomo Rozen

  DOI：10.1021/jo9723366

  日期：1998.7.1

  tert-Butyl hypofluorite, t-BuOF, easily synthesized from t-BuOH and F-2, is a unique source of the novel electrophilic tert-butoxylium moiety t-BuO+. It was added to several benzylic double bonds to form vicinal fluoro-tert-butoxide derivatives. Not surprisingly, this bulky reagent is quite sensitive to steric hindrance. The process is electrophilic in nature, but since the reaction is relatively slow (20-60 min) formation of various radical species can take place, forming eventually several distinct byproducts. t-BuOF was also reacted with a number of enols, producing the corresponding alpha-tert-butoxy ketone derivatives in moderate to good yields. The best results were obtained with benzylic enol derivatives.