4-(2-甲基苯基)-4-氧代丁酸甲酯 | 85616-39-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-(2-甲基苯基)-4-氧代丁酸甲酯
• 英文名称: methyl 4-oxo-4-o-tolylbutyrate
• 英文别名: methyl 4-(2-methylphenyl)-4-oxobutanoate；4-oxo-4-o-tolyl-butyric acid methyl ester；4-Oxo-4-o-tolyl-buttersaeure-methylester
• CAS: 85616-39-3
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: YAHOPCAPQXOADV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 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：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2-甲基苯基)-4-氧代丁酸甲酯 生成 4-(2-甲基苯基)-4-氧代丁酸
  参考文献：
  名称：

  THE USE OF ORGANOCADMIUM REAGENTS FOR THE PREPARATION OF SUBSTITUTED β-AROYLPROPIONIC ACIDS

  摘要：

  DOI：

  10.1021/jo01150a010
• 作为产物：
  描述：

  邻甲苯基溴化镁 在 硫酸 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 4-(2-甲基苯基)-4-氧代丁酸甲酯
  参考文献：
  名称：

  Fluorescent Derivatives of AC-42 To Probe Bitopic Orthosteric/Allosteric Binding Mechanisms on Muscarinic M1 Receptors

  摘要：

  Two fluorescent derivatives of the M1 muscarinic selective agonist AC-42 were synthesized by coupling the lissamine rhodamine B fluorophore (in ortho and para positions) to AC42-NH2. This precursor) prepared according to an original seven-step procedure, was included in the study together with the LRB fluorophore (alone or linked to an alkyl chain). All these compounds are antagonists, but examination of their ability to inhibit or modulate orthosteric [H-3]NMS binding revealed that para-LRB-AC42 shared several properties with AC-42. Carefully designed experiments allowed para-LRB-AC42 to be used as a FRET tracer on EGFP-fused M1 receptors. Under equilibrium binding conditions, orthosteric ligands, AC-42, and the allosteric modulator gallamine behaved as competitors of para-LRB-AC42 binding whereas other allosteric compounds such as WIN 51,708 and N-desmethylclozapine were noncompetitive inhibitors. Finally, molecular modeling studies focused on putative orthosteric/allosteric bitopic poses for AC-42 and para-LRB-AC42 in a 3D model of the human M1 receptor.

  DOI：

  10.1021/jm201348t

文献信息

• Generation of Acyl Radicals from 1-Oxidoalkylidenechromium(0) Complexes by Treatment with Bis(2,2,6,6-tetramethyl-3,5-heptanedionato)copper(II) and Their Reactions with Olefins
  作者：Hidehiro Sakurai、Koichi Narasaka

  DOI：10.1246/cl.1994.2017

  日期：1994.11

  Tetramethylammonium pentacarbonyl(1-oxidoalkylidene)chromium(0) complexes are oxidized with bis(2,2,6,6-tetramethyl-3,5-heptanedionato)copper(II) to generate acyl radicals which react with electron-deficient olefins, giving intermolecular addition products.

  四甲基铵五羰基（1-氧化亚烷基）铬（0）配合物与双（2,2,6,6-四甲基-3,5-庚二酮）铜（II）氧化生成酰基自由基，与缺电子烯烃反应，得到分子间加成产物。
• Ribeiro, Odartey; Hadfield, Stephen T.; Clayton, Alexandra F., Journal of the Chemical Society. Perkin transactions I, 1983, # 1, p. 87 - 91
  作者：Ribeiro, Odartey、Hadfield, Stephen T.、Clayton, Alexandra F.、Vose, Colin W.、Coombs, Maurice M.

  DOI：——

  日期：——
• Effect of Alkyl Substituents on Photorelease from Butyrophenone Derivatives
  作者：Sivaramakrishnan Muthukrishnan、Jagadis Sankaranarayanan、Tamara C. S. Pace、Armands Konosonoks、Mariel E. DeMichiei、Michael J. Meese、Cornelia Bohne、Anna D. Gudmundsdottir

  DOI：10.1021/jo9021088

  日期：2010.3.5

  Photolysis of 1a yields 4a in organ-saturated methanol, whereas 1b is photostable. Laser flash photolysis of 1a in acetonitrile shows formation of biradical 2a (lambda(max) = 380 nm, tau = similar to 60 ns), which undergoes intersystem crossing to form Z-3a (lambda(max) = 380 nm, tau = 270 ns) and E-3a (lambda(max) = 380 nm, tau = 300 ms). Z-3a regenerates the starting material, whereas E-3b undergoes intramolecular lactonization to release the alcohol moiety and form 4a. Similar laser flash photolysis of 1b shows formation of biradical 2b (lambda(max) = 340 nm, tau = 1.9 mu s in acetonitrile), which is longer-lived than 2a is. However, 2b only undergoes intersystem crossing to form Z-3b (lambda(max) = 380 nm, tau = 4.3 mu s). Calculations demonstrate that intramolecular pseudo hydrogen bonding between the OH moiety and the radical centered on the isopropyl carbon in 2b and the bulkiness of the isopropyl group prevent the necessary rotation to form E-3b. In comparison, 2a does not form an intramolecular pseudo hydrogen bond between the methylene radical center and the OH group, and as a consequence, it undergoes intersystem crossing to form both E- and Z-3a.
• THE USE OF ORGANOCADMIUM REAGENTS FOR THE PREPARATION OF SUBSTITUTED β-AROYLPROPIONIC ACIDS
  作者：WILLIAM G. DAUBEN、HARRY TILLES

  DOI：10.1021/jo01150a010

  日期：1950.7
• Fluorescent Derivatives of AC-42 To Probe Bitopic Orthosteric/Allosteric Binding Mechanisms on Muscarinic M1 Receptors
  作者：Sandrine B. Daval、Céline Valant、Dominique Bonnet、Esther Kellenberger、Marcel Hibert、Jean-Luc Galzi、Brigitte Ilien

  DOI：10.1021/jm201348t

  日期：2012.3.8

  Two fluorescent derivatives of the M1 muscarinic selective agonist AC-42 were synthesized by coupling the lissamine rhodamine B fluorophore (in ortho and para positions) to AC42-NH2. This precursor) prepared according to an original seven-step procedure, was included in the study together with the LRB fluorophore (alone or linked to an alkyl chain). All these compounds are antagonists, but examination of their ability to inhibit or modulate orthosteric [H-3]NMS binding revealed that para-LRB-AC42 shared several properties with AC-42. Carefully designed experiments allowed para-LRB-AC42 to be used as a FRET tracer on EGFP-fused M1 receptors. Under equilibrium binding conditions, orthosteric ligands, AC-42, and the allosteric modulator gallamine behaved as competitors of para-LRB-AC42 binding whereas other allosteric compounds such as WIN 51,708 and N-desmethylclozapine were noncompetitive inhibitors. Finally, molecular modeling studies focused on putative orthosteric/allosteric bitopic poses for AC-42 and para-LRB-AC42 in a 3D model of the human M1 receptor.