4-(2-hydroxy-3,4,6-trimethylphenyl)-but-2-enal

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-(2-hydroxy-3,4,6-trimethylphenyl)-but-2-enal
• 英文别名: (E)-4-(2-hydroxy-3,4,6-trimethylphenyl)but-2-enal
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: IXGOTTNDELMJAN-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-trimethylsilyl-1,3-butadiene 、 2,3,5-三甲基苯酚 在 [双(三氟乙酰氧基)碘]苯 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以44%的产率得到4-(2-hydroxy-3,4,6-trimethylphenyl)-but-2-enal
  参考文献：
  名称：

  Oxidized Arenol Intermediates in Intermolecular Carbon−Carbon Bond Formation. Naphthoid Cyclohexa-2,4-dienones via Oxidative Nucleophilic Substitution

  摘要：

  [GRAPHICS]Dearomatization of arenes is a powerful strategy for the preparation of functionalized cyclic olefins, Phenol oxidation can be exploited as a dearomatization tactic to produce cyclohexa-2,4-dienones. lodine(lll)-mediated oxidation of 2-alkyl- and 5-alkoxynaphthols was accomplished in the presence of an allylsilane or a silyl enol ether carbon-based nucleophile to furnish cyclohexa-2,4-dienone derivatives in moderate to good yields. This intermolecular carbon-carbon bond-forming reaction is particularly promising for the preparation of synthetically valuable naphthoid orthoquinols.

  DOI：

  10.1021/ol9910363

文献信息

• Oxidized Arenol Intermediates in Intermolecular Carbon−Carbon Bond Formation. Naphthoid Cyclohexa-2,4-dienones via Oxidative Nucleophilic Substitution
  作者：Stéphane Quideau、Matthew A. Looney、Laurent Pouységu

  DOI：10.1021/ol9910363

  日期：1999.11.1

  [GRAPHICS]Dearomatization of arenes is a powerful strategy for the preparation of functionalized cyclic olefins, Phenol oxidation can be exploited as a dearomatization tactic to produce cyclohexa-2,4-dienones. lodine(lll)-mediated oxidation of 2-alkyl- and 5-alkoxynaphthols was accomplished in the presence of an allylsilane or a silyl enol ether carbon-based nucleophile to furnish cyclohexa-2,4-dienone derivatives in moderate to good yields. This intermolecular carbon-carbon bond-forming reaction is particularly promising for the preparation of synthetically valuable naphthoid orthoquinols.