4-Hydroxy-3,5-dimethyl-benzalaceton | 7733-53-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 4-Hydroxy-3,5-dimethyl-benzalaceton
• 英文别名: 4-(4-hydroxy-3,5-dimethylphenyl)but-3-en-2-one
• CAS: 7733-53-1
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: PIVDVDIWHFLDEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-Hydroxy-3,5-dimethyl-benzalaceton 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、800.01 kPa 条件下， 生成 4-(3,5-Dimethyl-4-hydroxyphenyl)butan-2-one
  参考文献：
  名称：

  10.1002/ejoc.202400267

  摘要：

  A catalytic strategy towards the tribromide‐catalyzed dearomative spirocyclization reaction is described employing tetrabutylammonium bromide (TBAB) and oxone as an oxidising agent. This methodology leads to the exclusive formation of spirofurano dienones without rearomatization or halogenation. Our group has been on trails of tribromide‐catalyzed dearomative transformation during the last decade, and now this exhibits the first report which delivers high functional group tolerance and broad substrate scope with excellent yield (up to 99%) and good diastereoselectivity (dr up to 14:1). The oxidation of naphthols as well as phenols is achieved under this mild conditions.

  DOI：

  10.1002/ejoc.202400267
• 作为产物：
  描述：

  2,6-二甲基苯酚 在 sodium hydroxide 作用下， 以 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 5.0h， 生成 4-Hydroxy-3,5-dimethyl-benzalaceton
  参考文献：
  名称：

  10.1002/ejoc.202400267

  摘要：

  A catalytic strategy towards the tribromide‐catalyzed dearomative spirocyclization reaction is described employing tetrabutylammonium bromide (TBAB) and oxone as an oxidising agent. This methodology leads to the exclusive formation of spirofurano dienones without rearomatization or halogenation. Our group has been on trails of tribromide‐catalyzed dearomative transformation during the last decade, and now this exhibits the first report which delivers high functional group tolerance and broad substrate scope with excellent yield (up to 99%) and good diastereoselectivity (dr up to 14:1). The oxidation of naphthols as well as phenols is achieved under this mild conditions.

  DOI：

  10.1002/ejoc.202400267

文献信息

• Rajakumar; Rao, Pharmazie, 1994, vol. 49, # 7, p. 516 - 519
  作者：Rajakumar、Rao

  DOI：——

  日期：——
• 10.1002/ejoc.202400267
  作者：Kuila, Puspendu、Roy, Barnali、Sarkar, Debayan

  DOI：10.1002/ejoc.202400267

  日期：——

  A catalytic strategy towards the tribromide‐catalyzed dearomative spirocyclization reaction is described employing tetrabutylammonium bromide (TBAB) and oxone as an oxidising agent. This methodology leads to the exclusive formation of spirofurano dienones without rearomatization or halogenation. Our group has been on trails of tribromide‐catalyzed dearomative transformation during the last decade, and now this exhibits the first report which delivers high functional group tolerance and broad substrate scope with excellent yield (up to 99%) and good diastereoselectivity (dr up to 14:1). The oxidation of naphthols as well as phenols is achieved under this mild conditions.