1-(4-chlorophenyl)-5-phenyl-1H-pyrazole-3-carboxylic acid ethyl ester | 62160-92-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(4-chlorophenyl)-5-phenyl-1H-pyrazole-3-carboxylic acid ethyl ester
• 英文别名: ethyl 1-(4-chlorophenyl)-5-phenyl-1H-pyrazole-3-carboxylate；3-ethoxycarbonyl-1-(4-chlorophenyl)-5-phenyl-1H-pyrazole；1-(4-chloro-phenyl)-5-phenyl-1H-pyrazole-3-carboxylic acid ethyl ester；1H-Pyrazole-3-carboxylic acid, 1-(4-chlorophenyl)-5-phenyl-, ethyl ester；ethyl 1-(4-chlorophenyl)-5-phenylpyrazole-3-carboxylate
• CAS: 62160-92-3
• 化学式: C₁₈H₁₅ClN₂O₂
• 分子量: 326.782
• InChiKey: KWIBTNACMQKSKT-UHFFFAOYSA-N

物化性质

• 熔点：
  79-80 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  483.9±40.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 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：

  1-(4-chlorophenyl)-5-phenyl-1H-pyrazole-3-carboxylic acid ethyl ester 在 锂硼氢 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 87.5h， 生成 3-bromomethyl-1-(4-chlorophenyl)-5-phenyl-1H-pyrazole
  参考文献：
  名称：

  New COX-2/5-LOX Inhibitors:  Apoptosis-Inducing Agents Potentially Useful in Prostate Cancer Chemotherapy

  摘要：

  The arachidonic acid metabolizing enzymes cyclooxygenase-2 (COX-2) and lipoxygenases (LOXs) have been found to be implicated in a variety of cancers, including prostate cancer. To develop new therapeutic treatments, it therefore seemed interesting to design dual COX-2/5-LOX inhibitors. We report here the synthesis and in vitro pharmacological properties of diarylpyrazole derivatives that have in their structure key pharmacophoric elements to obtain optimal interaction with subsites of active pockets in both enzyme systems. Using a molecular modeling approach, a set of SAR data is proposed, highlighting the importance of the sulfonyl group of one of the aryl moieties in terms of proliferation inhibition and/or apoptosis induction.

  DOI：

  10.1021/jm0407761
• 作为产物：
  描述：

  1-(4-chlorophenyl)-5-phenyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid ethyl ester 在 吡啶 、 sodium chloride 作用下， 以 水 、 乙酸乙酯 为溶剂， 以82 %的产率得到1-(4-chlorophenyl)-5-phenyl-1H-pyrazole-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  电化学使吡唑啉氧化芳构化

  摘要：

  吡唑是一种非常重要的结构基序，广泛存在于药物和农用化学品中。提出了一种通过吡唑啉的氧化芳构化可持续合成吡唑的电化学方法。廉价的氯化钠在双相系统（水/有机）中用作氧化还原介质和支持电解质的双重作用。该方法适用范围广，可以使用碳基电极在最简单的电解装置中进行。因此，该方法允许简单的后处理策略，例如提取和结晶，从而能够在技术相关的规模上应用这种绿色合成路线。多克规模电解的演示不会降低产量，这一点得到了强调。

  DOI：

  10.1039/d3ob00671a

文献信息

• Palladium-Catalyzed Chelation-Assisted Regioselective Oxidative Dehydrogenative Homocoupling/<i>Ortho</i>-Hydroxylation in <i>N</i>-Phenylpyrazoles
  作者：Harikrishna Batchu、Soumya Bhattacharyya、Ruchir Kant、Sanjay Batra

  DOI：10.1021/acs.joc.5b00733

  日期：2015.8.7

  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.
• 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.
• A new efficient synthesis of pyrazoles from hydrazonoyl halides and β-oxophosphonates
  作者：Aixue Sun、Jia-Hai Ye、Haitao Yu、Wenchao Zhang、Xiaolong Wang

  DOI：10.1016/j.tetlet.2013.12.045

  日期：2014.1

  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.
• When Aryldiazonium Salts Meet Vinyl Diazoacetates: A Cobalt-Catalyzed Regiospecific Synthesis of <i>N</i>-Arylpyrazoles
  作者：Haiheng Guo、Daming Zhang、Chenghao Zhu、Jian Li、Guangyang Xu、Jiangtao Sun

  DOI：10.1021/ol5012339

  日期：2014.6.6

  A cobalt-catalyzed C-N bond formation between aryl diazonium salts and vinyl diazoacetates has been developed under relatively mild conditions. The N-arylpyrazoles have been prepared in moderate to high yields in a regiospecific way.