ethyl 1-(4-bromophenyl)-5-phenyl-1H-pyrazole-3-carboxylate | 62160-91-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 1-(4-bromophenyl)-5-phenyl-1H-pyrazole-3-carboxylate
• 英文别名: 1-(4-bromo-phenyl)-5-phenyl-1H-pyrazole-3-carboxylic acid ethyl ester；1H-Pyrazole-3-carboxylic acid, 1-(4-bromophenyl)-5-phenyl-, ethyl ester；ethyl 1-(4-bromophenyl)-5-phenylpyrazole-3-carboxylate
• CAS: 62160-91-2
• 化学式: C₁₈H₁₅BrN₂O₂
• 分子量: 371.233
• InChiKey: FQFOAZVQXIKFSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 1-(4-bromophenyl)-5-phenyl-1H-pyrazole-3-carboxylate 在 dipotassium peroxodisulfate 、 palladium diacetate 作用下， 以 三氟乙酸 、 三氟乙酸酐 为溶剂， 反应 12.0h， 以40%的产率得到ethyl 1-(4-bromo-2-hydroxyphenyl)-5-phenyl-1H-pyrazole-3-carboxylate
  参考文献：
  名称：

  Palladium-Catalyzed Chelation-Assisted Regioselective Oxidative Dehydrogenative Homocoupling/Ortho-Hydroxylation in N-Phenylpyrazoles

  摘要：

  A palladium-catalyzed pyrazole-directed regioselective oxidative C(sp2)-H functionalization of the N-phenyl ring in N-phenylpyrazoles to afford either a biaryl bis-pyrazole (via dehydrogenative homocoupling) or N-(o-hydroxyphenyl)pyrazole (via C-H oxygenation) or their mixture is described. The substitutions on the N-phenyl ring and the pyrazole ring and the dilution of the reaction medium with respect to the TFA/TFAA mixture (substrate concentration) have a remarkable influence on the outcome of the reaction. It was discovered that if the reactions were performed under highly dilute conditions (ca. 10 times) then N-(o-hydroxyphenyl)pyrazoles were the major or the sole products.

  DOI：

  10.1021/acs.joc.5b00733
• 作为产物：
  描述：

  (2-氧代-2-苯乙基)膦酸二乙酯 、 乙基(2E)-[(4-溴苯基)亚肼基](氯)乙酸酯 在 lithium hydroxide 作用下， 以 乙二醇二甲醚 为溶剂， 反应 10.0h， 以95%的产率得到ethyl 1-(4-bromophenyl)-5-phenyl-1H-pyrazole-3-carboxylate
  参考文献：
  名称：

  A new efficient synthesis of pyrazoles from hydrazonoyl halides and β-oxophosphonates

  摘要：

  A new practical and efficient synthesis of 1,3,5-trisubstituted pyrazoles has been developed by reacting of hydrazonoyl halides with beta-oxophosphonates under mild conditions in good yields with excellent regioselectivity. This process employs an addition-elimination sequence. Wide scope, functional group compatibility has been established. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.12.045

文献信息

• Synthesis, central and peripheral benzodiazepine receptor affinity of pyrazole and pyrazole-containing polycyclic derivatives
  作者：Francesco Campagna、Fausta Palluotto、Angelo Carotti、Elisabetta Maciocco

  DOI：10.1016/j.farmac.2004.05.008

  日期：2004.11

  A series of new pyrazole-condensed 6,5,5 tricyclic compounds were synthesized and tested to evaluate their binding affinities at both central (CBR) and peripheral (PBR) benzodiazepine receptors. Some 1-aryl-5-phenylpyrazole derivatives were also prepared and tested for comparison with their corresponding rigid tricyclic analogs. Among the newly synthesized 1-aryl-1,4-dihydro-indeno[1,2-c]pyrazoles bearing both an ethoxycarbonyl group at position 3 and a carbonyl function at the position 4, compound 4b emerged as a new potent (IC(50) = 26.4 nM) and selective CBR ligand. The 4-oxo-1-aryl-1,4-dihydro-indeno[1,2-c]pyrazole diethylamide derivative 14a was instead identified as a relatively potent (IC(50) = 124 nM) but highly selective PBR ligand.