p-bromophenacyl trimethylacetate | 53756-57-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-bromophenacyl trimethylacetate
• 英文别名: 2-(4-bromophenyl)-2-oxoethyl pivalate；Trimethylessigsaeure-p-bromphenacylester；Pivalinsaeure-p-bromphenacylester；Pivalinsaeure- (¹⁴C-markiert)；Trimethyl-essigsaeure-(4-brom-phenacylester)；1-(4-bromo-phenyl)-2-pivaloyloxy-ethanone；1-(4-Brom-phenyl)-2-pivaloyloxy-aethanon；[2-(4-Bromophenyl)-2-oxoethyl] 2,2-dimethylpropanoate
• CAS: 53756-57-3
• 化学式: C₁₃H₁₅BrO₃
• 分子量: 299.164
• InChiKey: KPWLWMMBFGZQJE-UHFFFAOYSA-N

物化性质

• 熔点：
  77.0-77.4 °C(Solv: water (7732-18-5); ethanol (64-17-5))
• 沸点：
  365.9±22.0 °C(Predicted)
• 密度：
  1.340±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  p-bromophenacyl trimethylacetate 在 (S)-(+)-5,5'-双[二(3,5-二叔丁基-4-甲氧基苯基)膦]-4,4'-二-1,3-苯并二氧戊环 、 palladium(II) trifluoroacetate 、 氢气 作用下， 以 乙醇 、 2,2,2-三氟乙醇 为溶剂， 20.0 ℃ 、3.0 MPa 条件下， 反应 24.0h， 以94%的产率得到
  参考文献：
  名称：

  Palladium-Catalyzed Asymmetric Hydrogenation of α-Acyloxy-1-arylethanones

  摘要：

  First hand: The first example of a palladium-catalyzed asymmetric hydrogenation of α-acyloxy ketones (1) was accomplished to give the hydrogenated products 2 with by far the highest catalytic efficiency in up to quantitative conversions and excellent enantioselectivities. The hydrogenated products could serve as important intermediates for the preparation of many drug candidates. TFE=2,2,2-trifluoroethanol.

  DOI：

  10.1002/anie.201306231
• 作为产物：
  描述：

  4-溴苯乙酮 在 溴 、 四丁基碘化铵 、 potassium carbonate 作用下， 以 乙醚 、 二氯甲烷 、 水 为溶剂， 生成 p-bromophenacyl trimethylacetate
  参考文献：
  名称：

  Palladium-Catalyzed Asymmetric Hydrogenation of α-Acyloxy-1-arylethanones

  摘要：

  First hand: The first example of a palladium-catalyzed asymmetric hydrogenation of α-acyloxy ketones (1) was accomplished to give the hydrogenated products 2 with by far the highest catalytic efficiency in up to quantitative conversions and excellent enantioselectivities. The hydrogenated products could serve as important intermediates for the preparation of many drug candidates. TFE=2,2,2-trifluoroethanol.

  DOI：

  10.1002/anie.201306231

文献信息

• <b>Some New</b> <i>p</i><b>-Bromophenacyl Esters.</b>
  作者：S. G. Powell

  DOI：10.1021/ja01354a501

  日期：1931.3
• Bartsch, Richard A.; Phillips, John B., Synthetic Communications, 1986, vol. 16, # 14, p. 1777 - 1780
  作者：Bartsch, Richard A.、Phillips, John B.

  DOI：——

  日期：——
• Potassium fluoride assisted derivatization of carboxylic acids to phenacyl esters for determination by high-performance liquid chromatography
  作者：Jack M. Miller、Ian D. Brindle、Stephen R. Cater、Kwok-Hung. So、James H. Clark

  DOI：10.1021/ac50064a047

  日期：1980.12.1
• BARTSCH R. A.; PHILLIPS J. B., SYNTH. COMMUN., 16,(1986) N 14, 1777-1780
  作者：BARTSCH R. A.、 PHILLIPS J. B.

  DOI：——

  日期：——
• Palladium-Catalyzed Asymmetric Hydrogenation of α-Acyloxy-1-arylethanones
  作者：Jianzhong Chen、Delong Liu、Nicholas Butt、Chao Li、Dongyang Fan、Yangang Liu、Wanbin Zhang

  DOI：10.1002/anie.201306231

  日期：2013.10.25

  First hand: The first example of a palladium-catalyzed asymmetric hydrogenation of α-acyloxy ketones (1) was accomplished to give the hydrogenated products 2 with by far the highest catalytic efficiency in up to quantitative conversions and excellent enantioselectivities. The hydrogenated products could serve as important intermediates for the preparation of many drug candidates. TFE=2,2,2-trifluoroethanol.