(Z)-2-methyl-4-(2,3,5,6-tetramethylphenyl)-3-buten-2-ol

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (Z)-2-methyl-4-(2,3,5,6-tetramethylphenyl)-3-buten-2-ol
• 英文别名: (Z)-2-methyl-4-(2,3,5,6-tetramethylphenyl)but-3-en-2-ol
• 化学式: C₁₅H₂₂O
• 分子量: 218.339
• InChiKey: KYEWJHLNZFRHJK-FPLPWBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-碘-1,2,4,5-四甲基苯 在 platinum(IV) oxide 、 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 氢气 、 二乙胺 作用下， 以 乙酸乙酯 为溶剂， 45.0 ℃ 、101.33 kPa 条件下， 反应 4.0h， 生成 (Z)-2-methyl-4-(2,3,5,6-tetramethylphenyl)-3-buten-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