2-(1,3-dioxolan-2-ylmethyl)-4-methoxyphenol | 141989-04-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(1,3-dioxolan-2-ylmethyl)-4-methoxyphenol
• 英文别名: 2-(1,3-Dioxolan-2-ylmethyl)-4-methoxyphenol
• CAS: 141989-04-0
• 化学式: C₁₁H₁₄O₄
• 分子量: 210.23
• InChiKey: BUEQLEPCSUKKAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲醇 、 2-(1,3-dioxolan-2-ylmethyl)-4-methoxyphenol 在 potassium carbonate 、 thallium(III) nitrate 作用下， 以94%的产率得到2-(1,3-dioxolan-2-ylmethyl)-4,4-dimethoxy-2,5-cyclohexadienone
  参考文献：
  名称：

  烷基化的4,4-二甲氧基-2,5-环己二酮在甲醇中的光化学。（±）-去氧-2,5-二氢甲基松香霉素A的甲酯的合成

  摘要：

  在甲醇中辐照烷基化的4,4-二甲氧基-2,5-环己二酮，以合理的收率得到2-环戊烯酮衍生物。使用该光化学反应作为关键步骤，由2,3-二甲基对苯二酚单甲醚分四个步骤，以36％的总收率制备（±）-脱环氧-2,5-二氢甲基苯菌灵A的甲酯。

  DOI：

  10.1016/0040-4039(92)88165-2
• 作为产物：
  描述：

  2-(5-甲氧基-2-苯基甲氧基苯基)乙醛 在 palladium on activated charcoal 氢气 、 对甲苯磺酸 作用下， 以 乙酸乙酯 、 苯 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 6.0h， 生成 2-(1,3-dioxolan-2-ylmethyl)-4-methoxyphenol
  参考文献：
  名称：

  Photochemistry of Substituted 4,4-Dimethoxy-2,5-Cyclohexadienones

  摘要：

  Abstract4,4‐Dimethoxy‐2,5‐cyclohexadienones 9–14 were prepared from the corresponding hydroquinone monomethyl ethers by oxidation with thallium trinitrate in methanol. Irradiation of solutions of 9–13 in methanol with a broad band of UV light centered at 350 nm in a Rayonet reactor afforded 2‐cyclopentenone derivatives 15–19 in moderate to excellent yields, whereas irradiation of 14 in methanol gave phenol 8 along with other unidentified products. Irradiation of 11–14 in benzene yielded substituted phenols. The plausible reaction pathways for the product formation are discussed.

  DOI：

  10.1002/jccs.199800001

文献信息

• Photochemistry of alkylated 4,4-dimethoxy-2,5-cyclohexadienones in methanol. Synthesis of methyl ester of (±)-desepoxy-2,5-didehydromethylenomycin A
  作者：Fang-Tsao Hong、Kung-Shing Lee、Chun-Chen Liao

  DOI：10.1016/0040-4039(92)88165-2

  日期：1992.4

  Alkylated 4,4-dimethoxy-2,5-cyclohexadienones were irradiated in methanol to give 2-cyclopentenones derivatives in fair yields. Methyl ester of (±)-desepoxy-2,5-didehydromethylenomycin A was prepared from 2,3-dimethylhydroquinone monomethyl ether in four steps and 36% overall yield using this photochemical reaction as a key step.

  在甲醇中辐照烷基化的4,4-二甲氧基-2,5-环己二酮，以合理的收率得到2-环戊烯酮衍生物。使用该光化学反应作为关键步骤，由2,3-二甲基对苯二酚单甲醚分四个步骤，以36％的总收率制备（±）-脱环氧-2,5-二氢甲基苯菌灵A的甲酯。
• Photochemistry of Substituted 4,4-Dimethoxy-2,5-Cyclohexadienones
  作者：Fang-Tsao Hong、Kung-Shing Lee、Yow-Fu Tsai、Chun-Chen Liao

  DOI：10.1002/jccs.199800001

  日期：1998.2

  Abstract4,4‐Dimethoxy‐2,5‐cyclohexadienones 9–14 were prepared from the corresponding hydroquinone monomethyl ethers by oxidation with thallium trinitrate in methanol. Irradiation of solutions of 9–13 in methanol with a broad band of UV light centered at 350 nm in a Rayonet reactor afforded 2‐cyclopentenone derivatives 15–19 in moderate to excellent yields, whereas irradiation of 14 in methanol gave phenol 8 along with other unidentified products. Irradiation of 11–14 in benzene yielded substituted phenols. The plausible reaction pathways for the product formation are discussed.