2-ethyl-3-hydroxy-1-(2',4'-dihydroxyphenyl)propanone | 230976-76-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-ethyl-3-hydroxy-1-(2',4'-dihydroxyphenyl)propanone
• CAS: 230976-76-8
• 化学式: C₁₁H₁₄O₄
• 分子量: 210.23
• InChiKey: FRUOUXUERLTEPG-UHFFFAOYSA-N

物化性质

• 沸点：
  424.7±24.0 °C(Predicted)
• 密度：
  1.272±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  77.76
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  乙酸乙烯酯 、 2-ethyl-3-hydroxy-1-(2',4'-dihydroxyphenyl)propanone 在 Candida rugosa lipase (CRS, Type II) 作用下， 以 异丙醚 为溶剂， 反应 72.0h， 以55%的产率得到3-acetoxy-2-ethyl-1-(2',4'-dihydroxyphenyl)propanone
  参考文献：
  名称：

  Enzyme-Catalyzed Chemoselective Transesterification Reactions on Hydroxymethylated Phenolic Compounds

  摘要：

  The chemoselective capabilities of porcine pancreatic lipase (PPL) in tetrahydrofuran and Candida rugosa lipase (CRL) in diisopropyl ether have been investigated for selective acetylation and deacetylation of hydroxymethylated phenols and hydroxyaryl alkyl ketones and their peracetylated derivatives. Both PPL and CRL exhibited exclusive selectivity for the acetylation of alcoholic hydroxyl group over the phenolic hydroxyl group(s) of the hydroxymethylated phenols 1-5 and aryl alkyl ketones 6-9, and for the deacetylation of ester group involving the phenolic hydroxyl group over the ester group involving alcoholic hydroxyl of the peracetates 19-24. The preliminary results indicate that this strategy of chemoselective acetylation can also be used in the enantiomeric resolution of racemic ketones 6-9. Single crystal X-ray diffraction studies have confirmed the structures of compounds 4, 15, and 17. (C) 1999 Academic Press.

  DOI：

  10.1006/bioo.1998.1117
• 作为产物：
  描述：

  1-(4'-benzyloxy-2'-hydroxyphenyl)-2-ethyl-3-hydroxypropanone 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 25.0~30.0 ℃ 、101.32 kPa 条件下， 反应 2.0h， 以98%的产率得到2-ethyl-3-hydroxy-1-(2',4'-dihydroxyphenyl)propanone
  参考文献：
  名称：

  Enzyme-Catalyzed Chemoselective Transesterification Reactions on Hydroxymethylated Phenolic Compounds

  摘要：

  The chemoselective capabilities of porcine pancreatic lipase (PPL) in tetrahydrofuran and Candida rugosa lipase (CRL) in diisopropyl ether have been investigated for selective acetylation and deacetylation of hydroxymethylated phenols and hydroxyaryl alkyl ketones and their peracetylated derivatives. Both PPL and CRL exhibited exclusive selectivity for the acetylation of alcoholic hydroxyl group over the phenolic hydroxyl group(s) of the hydroxymethylated phenols 1-5 and aryl alkyl ketones 6-9, and for the deacetylation of ester group involving the phenolic hydroxyl group over the ester group involving alcoholic hydroxyl of the peracetates 19-24. The preliminary results indicate that this strategy of chemoselective acetylation can also be used in the enantiomeric resolution of racemic ketones 6-9. Single crystal X-ray diffraction studies have confirmed the structures of compounds 4, 15, and 17. (C) 1999 Academic Press.

  DOI：

  10.1006/bioo.1998.1117