2-oxo-4-(4-pentylphenyl)-but-3-enoic acid ethyl ester

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 2-oxo-4-(4-pentylphenyl)-but-3-enoic acid ethyl ester
• 英文别名: (E)-ethyl 2-oxo-4-(4-pentylphenyl)but-3-enoate；ethyl (E)-2-oxo-4-(4-pentylphenyl)but-3-enoate
• 化学式: C₁₇H₂₂O₃
• 分子量: 274.36
• InChiKey: NULFFOTYZOXSHW-OUKQBFOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 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：

  2-oxo-4-(4-pentylphenyl)-but-3-enoic acid ethyl ester 、 2,4-二氯苯肼盐酸盐 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 20.0h， 生成 1-(2,4-dichlorophenyl)-5-(4-pentylphenyl)-4,5-dihydro-1H-pyrazole-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Diaryl Dihydropyrazole-3-carboxamides with Significant In Vivo Antiobesity Activity Related to CB1 Receptor Antagonism:  Synthesis, Biological Evaluation, and Molecular Modeling in the Homology Model

  摘要：

  A number of analogues of diaryl dihydropyrazole-3-carboxamides have been synthesized. Their activities were evaluated for appetite suppression and body weight reduction in animal models. Depending on the chemical modification of the selected dihydropyrazole scaffold, the lead compounds-the bisulfate salt,of (+/-)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4,5-dihydro-1H-pyrazole-3-carboxylic acid morpholin-4-ylamide 26 and the bisulfate salt of (-)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4,5-dihydro-1H-pyrazole3-carboxylic acid morpholin-4-ylamide 30-showed significant body weight reduction in vivo, which is attributed to their CB1 antagonistic activity and exhibited a favorable pharmacokinetic profile. The molecular modeling studies also showed interactions of two isomers of (+/-)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)4,5-dihydro- 1H-pyrazole-3-carboxylic acid morpholin-4-ylamide 9 with CB I receptor in the homology model similar to those of N-piperidino-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-3-pyrazole-carboxarnide (rimonabant) 1 and 4S-(-)-3-(4-chlorophenyl)-N-methyl-N'-[(4-chlorophenyl)-sulfonyl]-4-pheny1-4,5-dihydro-1H-pyrazole-1-carboxamidine (SLV-319) 2.

  DOI：

  10.1021/jm061490u
• 作为产物：
  描述：

  乙醛酸乙酯 、 4-戊基苯乙炔 在 吗啉 、 copper(I) bromide 作用下， 以 1,4-二氧六环 为溶剂， 以62%的产率得到2-oxo-4-(4-pentylphenyl)-but-3-enoic acid ethyl ester
  参考文献：
  名称：

  CuBr-Promoted Formal Hydroacylation of 1-Alkynes with Glyoxal Derivatives: An Unexpected Synthesis of 1,2-Dicarbonyl-3-enes

  摘要：

  An efficient and concise protocol has been developed for the highly regio- and stereoselective synthesis of E-1,2-dicarbonyl-3-ene derivatives by a copper-promoted reaction of 1-alkynes with a-carbonyl aldehydes in the presence of morpholine. The products obtained are believed as the formal hydroacylation of the triple bond.

  DOI：

  10.1021/jo500199v

文献信息

• CuBr-Promoted Formal Hydroacylation of 1-Alkynes with Glyoxal Derivatives: An Unexpected Synthesis of 1,2-Dicarbonyl-3-enes
  作者：Shufeng Chen、Xiaojie Li、Haiying Zhao、Baoguo Li

  DOI：10.1021/jo500199v

  日期：2014.5.2

  An efficient and concise protocol has been developed for the highly regio- and stereoselective synthesis of E-1,2-dicarbonyl-3-ene derivatives by a copper-promoted reaction of 1-alkynes with a-carbonyl aldehydes in the presence of morpholine. The products obtained are believed as the formal hydroacylation of the triple bond.
• Diaryl Dihydropyrazole-3-carboxamides with Significant In Vivo Antiobesity Activity Related to CB1 Receptor Antagonism:  Synthesis, Biological Evaluation, and Molecular Modeling in the Homology Model
  作者：Brijesh Kumar Srivastava,*、Amit Joharapurkar、Saurin Raval、Jayendra Z. Patel、Rina Soni、Preeti Raval、Archana Gite、Amitgiri Goswami、Nisha Sadhwani、Neha Gandhi、Harilal Patel、Bhupendra Mishra、Manish Solanki、Bipin Pandey、Mukul R. Jain、Pankaj R. Patel

  DOI：10.1021/jm061490u

  日期：2007.11.1

  A number of analogues of diaryl dihydropyrazole-3-carboxamides have been synthesized. Their activities were evaluated for appetite suppression and body weight reduction in animal models. Depending on the chemical modification of the selected dihydropyrazole scaffold, the lead compounds-the bisulfate salt,of (+/-)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4,5-dihydro-1H-pyrazole-3-carboxylic acid morpholin-4-ylamide 26 and the bisulfate salt of (-)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4,5-dihydro-1H-pyrazole3-carboxylic acid morpholin-4-ylamide 30-showed significant body weight reduction in vivo, which is attributed to their CB1 antagonistic activity and exhibited a favorable pharmacokinetic profile. The molecular modeling studies also showed interactions of two isomers of (+/-)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)4,5-dihydro- 1H-pyrazole-3-carboxylic acid morpholin-4-ylamide 9 with CB I receptor in the homology model similar to those of N-piperidino-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-3-pyrazole-carboxarnide (rimonabant) 1 and 4S-(-)-3-(4-chlorophenyl)-N-methyl-N'-[(4-chlorophenyl)-sulfonyl]-4-pheny1-4,5-dihydro-1H-pyrazole-1-carboxamidine (SLV-319) 2.