4-(p-methylphenyl)-2-oxobutanoic acid | 121104-54-9

• 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: 4-(p-methylphenyl)-2-oxobutanoic acid
• 英文别名: 2-oxo-4-p-tolyl-butyric acid；2-Oxo-4-p-tolyl-buttersaeure；4-(4-Methylphenyl)-2-oxobutanoic acid
• CAS: 121104-54-9
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: KKWIVXSNWOATPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(p-methylphenyl)-2-oxobutanoic acid 在 [RuCl(benzene)(S)-SunPhos]Cl 、 氢溴酸 、 氢气 作用下， 以 四氢呋喃 、 水 为溶剂， 70.0 ℃ 、2.76 MPa 条件下， 反应 20.0h， 生成 (2S)-2-hydroxy-4-(4-methylphenyl)butanoic acid
  参考文献：
  名称：

  Highly enantioselective hydrogenation of 2-oxo-4-arybutanoic acids to 2-hydroxy-4-arylbutanoic acids

  摘要：

  The Ru-catalyzed asymmetric hydrogenation of 2-oxo-4-arybutanoic acids to afford 2-hydroxy-4-arybutanoic acids was accomplished by employing SunPhos as chiral ligand and 1 M aq HBr as additive. The high enantioselectivities (88.4%-92.6% ee) and efficiency (TON=10,000, TOF=300 h(-1)) make this method efficient for the synthesis of an important intermediate, (R)-2-hydroxy-4-phenylbutanoic acid, for ACE inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.06.071
• 作为产物：
  描述：

  4-甲基苯乙基溴 在 碘 、 magnesium 、 三氟乙酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 4-(p-methylphenyl)-2-oxobutanoic acid
  参考文献：
  名称：

  Structure–Activity Relationship Studies of α-Ketoamides as Inhibitors of the Phospholipase A and Acyltransferase Enzyme Family

  摘要：

  The phospholipase A and acyltransferase (PLAAT) family of cysteine hydrolases consists of five members, which are involved in the Ca2+-independent production of N-acylphosphatidylethanolamines (NAPEs). NAPEs are lipid precursors for bioactive N-acylethanolamines (NAEs) that are involved in various physiological processes such as food intake, pain, inflammation, stress, and anxiety. Recently, we identified alpha-ketoamides as the first pan-active PLAAT inhibitor scaffold that reduced arachidonic acid levels in PLAAT3-overexpressing U2OS cells and in HepG2 cells. Here, we report the structure-activity relationships of the alpha-ketoamide series using activity-based protein profiling. This led to the identification of LEI-301, a nanomolar potent inhibitor for the PLAAT family members. LEI-301 reduced the NAE levels, including anandamide, in cells overexpressing PLAAT2 or PLAAT5. Collectively, LEI-301 may help to dissect the physiological role of the PLAATs.

  DOI：

  10.1021/acs.jmedchem.0c00522

文献信息

• Synthesis of γ-Butyrolactones, Quinoxalines, and Azauracils from 4-Aryl-2-oxobutanoic Acid Derivatives
  作者：G. H. Labib、M. Abdel Rahman、Y. El-Kilany、A. I. El-Massry、E. S. H. El-Ashry

  DOI：10.1246/bcsj.61.4427

  日期：1988.12

  the corresponding 4-aryl-2-oxobutanoic acids (1). The anticipated products from the reaction of the furanones (2) with o-phenylenediamine (3) have not been isolated, but products resulting from the condensation followed by retro-aldol type of reaction are obtained and determined as 3-(2-arylethyl)-2(1H)-quinoxalinones (4). Compounds 4 could be readily obtained by the condensation of 3 with 1. 4-Aryl-2-oxobutanoic

  4-芳烷基-5-芳基-3-羟基-2(5H)-呋喃酮(2)已由相应的4-芳基-2-氧代丁酸(1)制备。呋喃酮 (2) 与邻苯二胺 (3) 反应的预期产物尚未分离，但得到缩合反应后的反醇醛型反应产物并确定为 3-(2-芳乙基) -2(1H)-喹喔啉酮 (4)。化合物4可以通过3与1的缩合容易地获得。4-芳基-2-氧代丁酸缩氨基硫脲(5)已经环化为5-(2-芳乙基)-6-氮杂尿嘧啶(6)。
• Cordier, Bulletin de la Societe Chimique de France, 1956, p. 564,568
  作者：Cordier

  DOI：——

  日期：——
• LABIB, G. H.;RAHMAN, M. ABDEL;EL-KILANY, Y.;EL-MASSRY, A. I.;EL-ASHRY, E.+, BULL. CHEM. SOC. JAP., 61,(1988) N2, C. 4427-4430
  作者：LABIB, G. H.、RAHMAN, M. ABDEL、EL-KILANY, Y.、EL-MASSRY, A. I.、EL-ASHRY, E.+

  DOI：——

  日期：——