ethyl 1-(2-oxo-2-phenylethyl)-3-phenyl-1H-pyrazole-5-carboxylate | 618070-56-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 1-(2-oxo-2-phenylethyl)-3-phenyl-1H-pyrazole-5-carboxylate
• 英文别名: ethyl 2-phenacyl-5-phenylpyrazole-3-carboxylate
• CAS: 618070-56-7
• 化学式: C₂₀H₁₈N₂O₃
• 分子量: 334.375
• InChiKey: RXWKKVODGOYUKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  61.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 1-(2-oxo-2-phenylethyl)-3-phenyl-1H-pyrazole-5-carboxylate 在 formamide 、 溶剂黄146 作用下， 以78%的产率得到2,6-diphenylpyrazolo[1,5-a]pyrazin-4(5H)-one
  参考文献：
  名称：

  Synthesis, X-ray crystal structure and fluorescent spectra of novel pyrazolo[1,5-a]pyrazin-4(5H)-one derivatives

  摘要：

  A series of fluorescent compounds, containing pyrazolo[1,5-a]pyrazin-4(5H)-one moiety, were designed and synthesized from ethyl 1-(2-oxo-2-phenylethyl)-3-phenyl-1H-pyrazole-5-carboxylates. The structures of the compounds have been confirmed by IR, (1)H NMR, HRMS and X-ray crystal diffraction. The optical properties of the compounds were investigated by UV-vis absorption and fluorescence spectroscopy. The effect of pH on the UV-vis absorption of compound 2a in methanol-H(2)O solutions was studied and interpreted by theory calculation. The pK(a), value of compound 2a was determined by the absorption spectra. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2011.06.025
• 作为产物：
  描述：

  5-苯基吡唑-3-羧酸乙酯 、 2-溴苯乙酮 生成 ethyl 1-(2-oxo-2-phenylethyl)-3-phenyl-1H-pyrazole-5-carboxylate
  参考文献：
  名称：

  Synthesis, X-ray crystal structure and fluorescent spectra of novel pyrazolo[1,5-a]pyrazin-4(5H)-one derivatives

  摘要：

  A series of fluorescent compounds, containing pyrazolo[1,5-a]pyrazin-4(5H)-one moiety, were designed and synthesized from ethyl 1-(2-oxo-2-phenylethyl)-3-phenyl-1H-pyrazole-5-carboxylates. The structures of the compounds have been confirmed by IR, (1)H NMR, HRMS and X-ray crystal diffraction. The optical properties of the compounds were investigated by UV-vis absorption and fluorescence spectroscopy. The effect of pH on the UV-vis absorption of compound 2a in methanol-H(2)O solutions was studied and interpreted by theory calculation. The pK(a), value of compound 2a was determined by the absorption spectra. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2011.06.025

文献信息

• Synthesis, crystal structure and biological evaluation of novel 2-(5-(hydroxymethyl)-3-phenyl-1H-pyrazol-1-yl)-1-phenylethanol derivatives
  作者：Liang-Wen Zheng、Jian Zhu、Bao-Xiang Zhao、Yao-Hui Huang、Jun Ding、Jun-Ying Miao

  DOI：10.1016/j.ejmech.2010.09.041

  日期：2010.12

  A series of novel 2-(5-(hydroxymethyl)-3-phenyl-1H-pyrazol-1-yl)-1-phenylethanol derivatives (4) was synthesized from ethyl 1-(2-oxo-2-phenylethyl)-3-phenyl-1H-pyrazole-5-carboxylate derivatives (3) and characterized by means of IR, 1H NMR, HRMS and X-ray crystal diffraction. Structures of 4a, 4d, 4e and 4f were also determined by 13C NMR. Isomeric intermediates, 3a and 5a, were unambiguously confirmed

  由乙基1-（2-氧代-2-苯基乙基）-合成了一系列新颖的2-（5-（羟甲基）-3-苯基-1H-吡唑-1-基）-1-苯基乙醇衍生物（4）。 3-苯基-1 H-吡唑-5-羧酸酯衍生物（3），并通过IR，1 H NMR，HRMS和X射线晶体衍射进行表征。还通过13 C NMR确定4a，4d，4e和4f的结构。X射线晶体结构分析明确证实了异构体中间体3a和5a，并成功地与1进行了区分。结合到吡唑环上的亚甲基的1 H NMR化学位移。初步生物学评估表明，化合物4d和4e可通过细胞周期阻滞和自噬抑制A549肺癌细胞的生长。
• Solvent-free microwave-assisted synthesis of tetrahydrooxazolo[3,2-a]pyrazolo[1,5-d]pyrazin-5-ones
  作者：Shi-Li Shen、Liang-Wen Zheng、Sheng-Qing Wang、Yan-Ru Zhang、Yuan Zhang、Ying Rui Liu、Bao-Xiang Zhao

  DOI：10.3998/ark.5550190.p008.083

  日期：——

  A series of novel oxazolo[3,2-a]pyrazolo[1,5-d]pyrazin-5-ones were synthesized by the reaction of ethyl 3-aryl-1-(2-oxo-2-arylethyl)-1H-pyrazole-5-carboxylate derivatives and aminoethanol under microwave-assisted one-step and solvent-free conditions.

  通过乙基3-芳基-1-(2-氧代-2-芳乙基)-1H-反应合成了一系列新型恶唑并[3,2-a]吡唑并[1,5-d]吡嗪-5-酮吡唑-5-羧酸衍生物和氨基乙醇在微波辅助一步和无溶剂条件下。
• Expeditious Synthesis and Single Crystal Structure of New Pyrazole-Fused 1,4-Oxazine
  作者：Liang-Wen Zheng、Bao-Xiang Zhao、Ying-Rui Liu

  DOI：10.1002/jhet.833

  日期：2012.5

  acids in the presence of Ac2O at reflux temperature. The products were isolated by simple filtration in excellent yields and were characterized by IR, 1H‐NMR, and HRMS. The molecular structure was confirmed by the X‐ray crystal analysis of one compound that was prone to crystallization.

  通过1-（2-氧代-2-苯基乙基）-3的内酯化反应合成了一系列2,6-二苯基-4 H-吡唑并[5,1- c ] [1,4]恶嗪-4-酮。在回流温度下，在Ac 2 O存在下，-1苯基1 H吡唑5羧酸。通过简单过滤将产物分离，收率很高，并通过IR，1 H-NMR和HRMS进行表征。通过一种易于结晶的化合物的X射线晶体分析证实了其分子结构。
• Synthesis, Crystal Structure, and DFT Study of Ethyl 1-(2-(Hydroxyimino)-2-phenylethyl)-3-phenyl-1H-pyrazole-5-carboxylate
  作者：Jin-Hui Zhou、Liang-Wen Zheng、Mao-Cai Yan、Mao-Jian Shi、Jing Liu、Guo-Qiang Shangguan

  DOI：10.1155/2017/6537402

  日期：——

  The crystal structure of ethyl 1-(2-(hydroxyimino)-2-phenylethyl)-3-phenyl-1H-pyrazole-5-carboxylate has been determined by X-ray single crystal diffraction. The crystal of the title compound is the monoclinic space group P2/c with unit cell parameters of A, A, A, , A3, and . The dihedral angles formed by the planes of the central pyrazole ring and the adjacent benzene rings are 73.60(7)° and 3.55(7)°

  1-(2-(羟基亚氨基)-2-苯基乙基)-3-苯基-1H-吡唑-5-羧酸乙酯的晶体结构已通过X射线单晶衍射确定。标题化合物的晶体为单斜空间群P2/c，晶胞参数为A、A、A、...、A3和...。中心吡唑环平面与相邻苯环平面形成的二面角分别为73.60(7)°和3.55(7)°。弱分子间 C-H2O 和 N- 氢键相互作用的结合稳定了晶体堆积。其 Z 和 E 异构体的几何形状和相应的过渡态 (TS) 以及其 Z 异构体的二聚体，使用 B3LYP 混合泛函与 def-TZVP 三-zeta 极化基组相结合进行了优化。Z二聚体优化结构的键角和键长与其单晶参数非常一致。双杂种功能 PWPB95-D3 与非常高精度的基组 def2-QZVP 相结合，用于评估每个异构体和 TS 的准确能量。Z 和 E 异构体之间计算的平衡常数对应于 4.29 的 [Z]/[E] 比率。计算分子范德华 (vdW)
• Synthesis of novel pyrazolo[1,5- a ]pyrazin-4(5 H )-one derivatives and their inhibition against growth of A549 and H322 lung cancer cells
  作者：Liang-Wen Zheng、Jin-Hui Shao、Bao-Xiang Zhao、Jun-Ying Miao

  DOI：10.1016/j.bmcl.2011.05.035

  日期：2011.7

  A series of substituted pyrazolo[1,5-a]pyrazin-4(5H)-one was synthesized by the reaction of ethyl 1-(2-oxo-2-phenylethyl)-3-phenyl-1H-pyrazole-5-carboxylate derivatives and 2-(2-aminoethoxy) ethanol or 2-morpholinoethanamine in the condition of microwave-assisted one-step and solvent-free in a good yield. The structures of the compounds were determined by IR, (1)H NMR and mass spectroscopy. In addition, a representative single-crystal structure was characterized by using X-ray diffraction analysis. Preliminary biological evaluation showed that the compounds could inhibit the growth of A549 and H322 cells in dosage-dependent manners. (C) 2011 Elsevier Ltd. All rights reserved.