ethyl 4-phenyl-3-methylquinoline-2-carboxylate | 154419-40-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: ethyl 4-phenyl-3-methylquinoline-2-carboxylate
• 英文别名: 2-ethoxycarbonyl-3-methyl-4-phenylquinoline；2-Quinolinecarboxylic acid, 3-methyl-4-phenyl-, ethyl ester；ethyl 3-methyl-4-phenylquinoline-2-carboxylate
• CAS: 154419-40-6
• 化学式: C₁₉H₁₇NO₂
• 分子量: 291.349
• InChiKey: YXYCTDOWDFYCNE-UHFFFAOYSA-N

物化性质

• 熔点：
  99-100 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  436.0±45.0 °C(Predicted)
• 密度：
  1.152±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 4-phenyl-3-methylquinoline-2-carboxylate 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 乙醇 为溶剂， 反应 26.0h， 生成 9-phenylfuro[3,4-b]quinolin-3(1H)-one
  参考文献：
  名称：

  Anzini, Maurizio; Capelli, Andrea; Vomero, Salvatore, Heterocycles, 1994, vol. 38, # 1, p. 103 - 112

  摘要：

  DOI：
• 作为产物：
  描述：

  3-bromomethyl-2-ethoxycarbonyl-4-phenylquinoline 在 potassium tert-butylate 、 乙醛 作用下， 以 苯 为溶剂， 反应 12.5h， 生成 ethyl 4-phenyl-3-methylquinoline-2-carboxylate
  参考文献：
  名称：

  Synthesis of 4-Substituted 11-Phenyl-1,2,3,4-tetrahydro-5H-azepino[3,4-b]quinolin-5-one Derivatives as Potential Peripheral Benzodiazepine-Receptor Ligands

  摘要：

  The synthesis of semirigid analogs of PK 11195, the highly specific peripheral benzodiazepine-receptor ligand, is reported. Compound (4) underwent the Wittig reaction with acetaldehyde to give olefin (7) which after allylic bromination was aminated to give the omega-amino esters (10a-c). These compounds were then hydrogenated and cyclized in boiling toluene with DMAP as catalyst. The standard procedure failed in the case of compound (10b), thus other cyclization procedures were examinated.

  DOI：

  10.3987/com-93-6662

文献信息

• Chlorotrimethylsilane-Mediated Friedländer Synthesis of Polysubstituted Quinolines
  作者：Dmitriy Volochnyuk、Sergey Ryabukhin、Andrey Plaskon、Vasiliy Naumchik、Andrei Tolmachev

  DOI：10.1055/s-2007-966003

  日期：2007.4

  New convenient conditions for the Friedlander synthesis of quinolines are described. Polysubstituted quinolines were readily prepared using chlorotrimethylsilane as a promoter and water-acceptor agent.

  描述了弗里德兰德合成喹啉的新便利条件。使用三甲基氯硅烷作为促进剂和吸水剂很容易制备多取代的喹啉。
• New iodinated quinoline-2-carboxamides for SPECT imaging of the translocator protein
  作者：Louise Stevenson、Adriana A.S. Tavares、Aurélie Brunet、Fiona I. McGonagle、Deborah Dewar、Sally L. Pimlott、Andrew Sutherland

  DOI：10.1016/j.bmcl.2009.12.061

  日期：2010.2

  With the aim of developing new SPECT imaging agents for the translocator protein (TSPO), a small library of iodinated quinoline-2-carboxamides have been prepared and tested for binding affinity with TSPO. N,N-Diethyl-3-iodomethyl-4-phenylquinoline-2-carboxamide was found to have excellent affinity (K-i 12.0 nM), comparable to that of the widely used TSPO imaging agent PK11195. (c) 2009 Elsevier Ltd. All rights reserved.
• Anzini, Maurizio; Capelli, Andrea; Vomero, Salvatore, Heterocycles, 1994, vol. 38, # 1, p. 103 - 112
  作者：Anzini, Maurizio、Capelli, Andrea、Vomero, Salvatore

  DOI：——

  日期：——
• Synthesis of 4-Substituted 11-Phenyl-1,2,3,4-tetrahydro-5H-azepino[3,4-b]quinolin-5-one Derivatives as Potential Peripheral Benzodiazepine-Receptor Ligands
  作者：Andrea Cappelli、Maurizio Anzini、Salvatore Vomero

  DOI：10.3987/com-93-6662

  日期：——

  The synthesis of semirigid analogs of PK 11195, the highly specific peripheral benzodiazepine-receptor ligand, is reported. Compound (4) underwent the Wittig reaction with acetaldehyde to give olefin (7) which after allylic bromination was aminated to give the omega-amino esters (10a-c). These compounds were then hydrogenated and cyclized in boiling toluene with DMAP as catalyst. The standard procedure failed in the case of compound (10b), thus other cyclization procedures were examinated.