6-acetoxy-2,2,5,8-tetramethylchromane | 600152-23-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6-acetoxy-2,2,5,8-tetramethylchromane
• CAS: 600152-23-6
• 化学式: C₁₅H₂₀O₃
• 分子量: 248.322
• InChiKey: QIBWTYQRFXTNHB-UHFFFAOYSA-N

物化性质

• 沸点：
  338.1±41.0 °C(Predicted)
• 密度：
  1.052±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.33
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  6-acetoxy-2,2,5,8-tetramethylchromane 在 甲醇 、 水 、 三氯化铁 、 potassium carbonate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 乙醚 、 甲苯 为溶剂， 反应 28.5h， 生成 8a-hydroxy-2,2,5,8-tetramethyl-2H,8aH-chromen-6-one
  参考文献：
  名称：

  Novel tocopheryl compounds XXV: synthesis and comparison of the para-quinones of all four homologous tocopherol model compounds and their 3,4-dehydro derivatives

  摘要：

  Four tocopherol model compounds, the chroman-6-ols (1-4) having the typical substitution pattern of alpha-, beta-, gamma-, and delta-tocopherol (vitamin E), were oxidized to the corresponding para-quinones (5-8), and dehydrogenated to the 2H-chromen-6-ols (17-20) involving initial acetyl protection of the phenolic OH and deprotection as the last step. The chromenols were also converted into the para-quinones (21-24), which existed in the bicyclic hemiketal form, in contrast to the chromanol-derived, monocyclic quinones 5-8, the ketalization behavior agreeing well with computations on the DFT level. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.03.114
• 作为产物：
  描述：

  6-hydroxy-2,2,5,8-tetramethylchroman 、 乙酸酐 在 吡啶 作用下， 反应 6.0h， 以98%的产率得到6-acetoxy-2,2,5,8-tetramethylchromane
  参考文献：
  名称：

  Novel tocopheryl compounds XXV: synthesis and comparison of the para-quinones of all four homologous tocopherol model compounds and their 3,4-dehydro derivatives

  摘要：

  Four tocopherol model compounds, the chroman-6-ols (1-4) having the typical substitution pattern of alpha-, beta-, gamma-, and delta-tocopherol (vitamin E), were oxidized to the corresponding para-quinones (5-8), and dehydrogenated to the 2H-chromen-6-ols (17-20) involving initial acetyl protection of the phenolic OH and deprotection as the last step. The chromenols were also converted into the para-quinones (21-24), which existed in the bicyclic hemiketal form, in contrast to the chromanol-derived, monocyclic quinones 5-8, the ketalization behavior agreeing well with computations on the DFT level. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.03.114