4-(2,5-dimethoxy-3,4,6-trimethylphenyl)-2-methyl-3-butyn-2-ol | 185757-83-9

• 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: 4-(2,5-dimethoxy-3,4,6-trimethylphenyl)-2-methyl-3-butyn-2-ol
• 英文别名: 4-(2,5-Dimethoxy-3,4,6-trimethylphenyl)-2-methylbut-3-yn-2-ol
• CAS: 185757-83-9
• 化学式: C₁₆H₂₂O₃
• 分子量: 262.349
• InChiKey: LPUGNKYQLMDFCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2,5-dimethoxy-3,4,6-trimethylphenyl)-2-methyl-3-butyn-2-ol 在 platinum(IV) oxide 氢气 、 4-甲基苯磺酸吡啶 、 乙酸酐 、 对甲苯磺酸 、 氢化奎宁 1,4-(2,3-二氮杂萘)二醚 作用下， 以 甲醇 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 4.0 ℃ 、303.98 kPa 条件下， 反应 48.0h， 生成 (S)-4-<2-(2,5-dimethoxy-3,4,6-trimethylphenyl)ethyl>-2,2,4-trimethyl<1,3>dioxolane
  参考文献：
  名称：

  Enantioselective Synthesis of the Chromane Moiety of Vitamin E

  摘要：

  Several new approaches for the enantioselective synthesis of the chromane moiety of vitamin E are described. Sonogashira coupling of 3a with the alkyne 4 and subsequent elimination gave 6, which was bis(hydroxylated) in 93% yield and with 85% ee. Recrystallization gave enantiopure 7a, which was hydrogenated and transformed into the vitamin E precursor 11. The bis(hydroxylation) of 18 and 21 to give 9 and 22, respectively, was less than satisfactory, proceeding with ee values of 28% and 18%. In contrast, stereoselective allylation of ketone 15 followed by removal of the protecting group or ozonolysis of the allyl moiety furnished the allyl alcohol 26 and the aldehyde 27, respectively, in almost enantiopure form, which again could be used as precursors for vitamin E. Partial hydrogenation of 5a gave the alkene 32a and that of 28 the alkene 30b, both of which show interesting atropisomerism.

  DOI：

  10.1002/(sici)1099-0690(199905)1999:5<1075::aid-ejoc1075>3.0.co;2-i
• 作为产物：
  描述：

  1,4-dimethoxy-2,3,5-trimethyl-benzene 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 硫酸 、 碘 、 高碘酸 、 二乙胺 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 19.0h， 生成 4-(2,5-dimethoxy-3,4,6-trimethylphenyl)-2-methyl-3-butyn-2-ol
  参考文献：
  名称：

  Enantioselective Synthesis of the Chromane Moiety of Vitamin E

  摘要：

  Several new approaches for the enantioselective synthesis of the chromane moiety of vitamin E are described. Sonogashira coupling of 3a with the alkyne 4 and subsequent elimination gave 6, which was bis(hydroxylated) in 93% yield and with 85% ee. Recrystallization gave enantiopure 7a, which was hydrogenated and transformed into the vitamin E precursor 11. The bis(hydroxylation) of 18 and 21 to give 9 and 22, respectively, was less than satisfactory, proceeding with ee values of 28% and 18%. In contrast, stereoselective allylation of ketone 15 followed by removal of the protecting group or ozonolysis of the allyl moiety furnished the allyl alcohol 26 and the aldehyde 27, respectively, in almost enantiopure form, which again could be used as precursors for vitamin E. Partial hydrogenation of 5a gave the alkene 32a and that of 28 the alkene 30b, both of which show interesting atropisomerism.

  DOI：

  10.1002/(sici)1099-0690(199905)1999:5<1075::aid-ejoc1075>3.0.co;2-i