3-hydroxy-3-(3-methoxyphenyl)butan-2-one | 104296-21-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-hydroxy-3-(3-methoxyphenyl)butan-2-one
• 英文别名: 3-Hydroxy-3-(3-methoxy-phenyl)-butan-2-on
• CAS: 104296-21-1
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: MCYOHJKDWIFSAI-UHFFFAOYSA-N

物化性质

• 沸点：
  148-151 °C(Press: 10 Torr)
• 密度：
  1.111±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-hydroxy-3-(3-methoxyphenyl)butan-2-one 在 lithium hydroxide 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 5-(3-methoxy-phenyl)-5-methyl-4-oxo-4,5-dihydro-furan-2-carboxylic acid
  参考文献：
  名称：

  Analogues of Acifran:  Agonists of the High and Low Affinity Niacin Receptors, GPR109a and GPR109b

  摘要：

  Recently identified GPCRs, GPR109a and GPR109b, the high and low affinity receptors for niacin, may represent good targets for the development of HDL elevating drugs for the treatment of atherosclerosis. Acifran, an agonist of both receptors, has been tested in human subjects, yet until recently very few analogs had been reported. We describe a series of acifran analogs prepared using newly developed synthetic pathways and evaluated as agonists for GPR109a and GPR109b, resulting in identification of compounds with improved activity at these receptors.

  DOI：

  10.1021/jm070022x
• 作为产物：
  描述：

  3-甲氧基苯乙酮 在 四丁基氟化铵 、 tert-butylammonium hexafluorophosphate(V) 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 3-hydroxy-3-(3-methoxyphenyl)butan-2-one
  参考文献：
  名称：

  酰基咪唑对芳香族酮的电还原酰化

  摘要：

  在氯代三甲基硅烷的存在下，通过电还原作用实现芳族酮与酰基咪唑的分子间还原偶联，得到α-三甲基甲硅烷氧基酮和酯。使用Bu 4 NPF 6作为支持电解质和THF中的Pb阴极可获得最佳结果。通过在THF中用TBAF处理，将含α-三甲基甲硅烷氧基的产物转化为相应的α-羟基酮和酯。该方法对于δ-和ε-酮基酰基咪唑的分子内还原偶联也是有效的。

  DOI：

  10.1021/jo051498w

文献信息

• Electroreductive Acylation of Aromatic Ketones with Acylimidazoles
  作者：Naoki Kise、Syun Agui、Shinji Morimoto、Nasuo Ueda

  DOI：10.1021/jo051498w

  日期：2005.11.1

  The intermolecular reductive coupling of aromatic ketones with acylimidazoles was effected by electroreduction in the presence of chlorotrimethylsilane and gave α-trimethylsiloxy ketones and esters. The best result was obtained using Bu4NPF6 as a supporting electrolyte and a Pb cathode in THF. The α-trimethylsiloxy-containing products were transformed to the corresponding α-hydroxy ketones and esters

  在氯代三甲基硅烷的存在下，通过电还原作用实现芳族酮与酰基咪唑的分子间还原偶联，得到α-三甲基甲硅烷氧基酮和酯。使用Bu 4 NPF 6作为支持电解质和THF中的Pb阴极可获得最佳结果。通过在THF中用TBAF处理，将含α-三甲基甲硅烷氧基的产物转化为相应的α-羟基酮和酯。该方法对于δ-和ε-酮基酰基咪唑的分子内还原偶联也是有效的。
• An Abnormal Reaction of an Organocadmium Reagent: para-Acylation of m-Methoxythenylcadmium Reagent
  作者：William G. Dauben、John W. Collette

  DOI：10.1021/ja01513a052

  日期：1959.3
• Analogues of Acifran:  Agonists of the High and Low Affinity Niacin Receptors, GPR109a and GPR109b
  作者：Jae-Kyu Jung、Benjamin R. Johnson、Tracy Duong、Marc Decaire、Jane Uy、Tawfik Gharbaoui、P. Douglas Boatman、Carleton R. Sage、Ruoping Chen、Jeremy G. Richman、Daniel T. Connolly、Graeme Semple

  DOI：10.1021/jm070022x

  日期：2007.4.1

  Recently identified GPCRs, GPR109a and GPR109b, the high and low affinity receptors for niacin, may represent good targets for the development of HDL elevating drugs for the treatment of atherosclerosis. Acifran, an agonist of both receptors, has been tested in human subjects, yet until recently very few analogs had been reported. We describe a series of acifran analogs prepared using newly developed synthetic pathways and evaluated as agonists for GPR109a and GPR109b, resulting in identification of compounds with improved activity at these receptors.