3-acetoxy-1-(4'-hydroxyphenyl)-2-methylpropanone | 92749-06-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-acetoxy-1-(4'-hydroxyphenyl)-2-methylpropanone
• 英文别名: 3-(4-Hydroxyphenyl)-2-methyl-3-oxopropyl acetate；[3-(4-hydroxyphenyl)-2-methyl-3-oxopropyl] acetate
• CAS: 92749-06-9
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: GCKOFCLHCPKCEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-acetoxy-1-(4'-hydroxyphenyl)-2-methylpropanone 、 溶剂黄146 在 一水合肼 作用下， 反应 2.0h， 以72%的产率得到4-(2,6-Dimethyl-6,7-dihydro-[1,3,4]oxadiazepin-5-yl)-phenol
  参考文献：
  名称：

  A Facile and General Synthesis of 2,5,6-Trisubstituted-6,7-dihydro-1,3,4-oxadiazepines

  摘要：

  DOI：

  10.1055/s-1984-30838
• 作为产物：
  描述：

  3-acetoxy-1-(4'-acetoxyphenyl)-2-methylpropanone 在 porcine pancreatic lipase (PPL, Type II) 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以60%的产率得到3-acetoxy-1-(4'-hydroxyphenyl)-2-methylpropanone
  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

文献信息

• CIGNARELLA, G.;BARLOCCO, D.;CURZU, M. M.;PINNA, G. A., SYNTHESIS, BRD, 1984, N 4, 342-345
  作者：CIGNARELLA, G.、BARLOCCO, D.、CURZU, M. M.、PINNA, G. A.

  DOI：——

  日期：——
• A Facile and General Synthesis of 2,5,6-Trisubstituted-6,7-dihydro-1,3,4-oxadiazepines
  作者：Giorgio Cignarella、Daniela Barlocco、Maria Michela Curzu、Gerard Aimé Pinna

  DOI：10.1055/s-1984-30838

  日期：——
• Enzyme-Catalyzed Chemoselective Transesterification Reactions on Hydroxymethylated Phenolic Compounds
  作者：Virinder S. Parmar、Ashok K. Prasad、Hari N. Pati、Rajesh Kumar、Abul Azim、Sucharita Roy、William Errington

  DOI：10.1006/bioo.1998.1117

  日期：1999.4

  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.