ethyl 4-(4-fluorophenyl)-2-oxo-6-phenylcyclohex-3-ene-1-carboxylate | 1024511-20-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 4-(4-fluorophenyl)-2-oxo-6-phenylcyclohex-3-ene-1-carboxylate
• CAS: 1024511-20-3
• 化学式: C₂₁H₁₉FO₃
• 分子量: 338.378
• InChiKey: QWIIFQFGVSOWJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 4-(4-fluorophenyl)-2-oxo-6-phenylcyclohex-3-ene-1-carboxylate 在 ammonium acetate 、 溶剂黄146 作用下， 反应 6.0h， 生成 ethyl 2-amino-4-(4-fluorophenyl)-6-phenylcyclohexa-1,3-diene-1-carboxylate
  参考文献：
  名称：

  Synthesis, Characterization and Crystal Structure of Ethyl 2-amino-4-(4-fluorophenyl)-6-phenylcyclohexa-1,3-diene-1-carboxylate

  摘要：

  Ethyl 2-amino-4-(4-fluorophenyl)-6-phenylcyclohexa-1,3-diene-1-carboxylate was synthesized from ethyl 6-(4-bromophenyl)-4-(4-fluorophenyl)-2-oxocyclohex-3-ene-1-carboxylate and ammonium acetate in glacial acetic acid. The synthesized compound was characterized by elemental analysis, FT-IR, thermogravimetric analysis (TGA), differential thermal analysis (DTA), UV-Visible, and single-crystal X-ray diffraction. The title compound, ethyl 2-amino-4-(4-fluorophenyl)-6-phenylcyclohexa-1,3-diene-1-carboxylate, C21H2OFNO2, crystallizes in the orthorhombic space group Pbca with the following unit-cell parameters: a = 17.417(2), b = 9.7287(9), c = 21.014(2) angstrom, and Z = 8. The crystal structure was solved by direct methods using single-crystal X-ray diffraction data collected at room temperature and refined by full-matrix least-squares procedures to a final R-value of 0.0644 for 1616 observed reflections. An intramolecular N-H horizontal ellipsis O hydrogen bond generates an S(6) graph-set motif. In the crystal, molecules are linked by N-H horizontal ellipsis O hydrogen bonds, forming a two-dimensional network.

  DOI：

  10.1080/15421406.2014.885348
• 作为产物：
  描述：

  乙酰乙酸乙酯 、 4'-fluorochalcone 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以66%的产率得到ethyl 4-(4-fluorophenyl)-2-oxo-6-phenylcyclohex-3-ene-1-carboxylate
  参考文献：
  名称：

  基于环己烯酮的类似物作为有效的非核苷逆转录酶抑制剂的合成、构效关系和分子对接

  摘要：

  摘要 化合物中的查耳酮核心是有利地选择有效的合成子，这为生物学和药理学研究提供了令人兴奋的前景。本研究报告使用合理的药物设计合成原则成功开发了八种新的基于环己烯酮的抗逆转录酶类似物。这些新的环己烯酮衍生物 (CDs) 是按照方便的 Robinson 环化路线合成的，这些 CDs 的分子结构后来通过 1 H NMR、13 C NMR、FT-IR、UV-Vis 光谱等各种分析技术证实和质谱。所有合成的化合物都针对逆转录酶 (RT) 进行了理论和实验筛选，并发现了具有潜在活性的逆转录酶 (RT) 抑制剂。在研究的化合物中，化合物 2FC4 在非核苷结合位点显示出与 RT 的高相互作用，分别贡献高自由结合能 (Δ G -8.01 Kcal) 和 IC 50 (0.207 μg/ml)。进一步的结果表明，与其他化合物相比，带有更多卤素基团的化合物具有额外的疏水性，具有更好的抗逆转录酶活性。预计本研究

  DOI：

  10.1016/j.molstruc.2014.12.090

文献信息

• Microwave synthesis, characterization and bio-efficacy evaluation of novel chalcone based 6-carbethoxy-2-cyclohexen-1-one and 2H-indazol-3-ol derivatives
  作者：N.A. Shakil、Manish K. Singh、M. Sathiyendiran、J. Kumar、Jasdeep C. Padaria

  DOI：10.1016/j.ejmech.2012.10.038

  日期：2013.1

  chalcones. Whereas, all the Indazole derivatives showed very good anti-oxidant activity and some were also found to be active as anti-bacterial agent. Among the screened compounds, 15 was found to be most active as anti-fungal agent (against Rhizoctonia solani, LC50 = 2.36 μg mL−1), 15b was found to be most active anti-bacterial agent (against Klebsiella pneumonia, MIC = 24.68 μg mL−1) and 14b emerged

  合成了基于查尔酮的新型6-乙氧基-2-环己烯-1-酮和2H-吲哚-3-醇衍生物，并使用诸如IR，1 H NMR，13 C NMR，COSY，DEPT和GC-MS等光谱技术对其进行了表征。筛选所有这些化合物的抗真菌，抗细菌和抗氧化活性。通常，环己烯酮衍生物显示出比亲代查尔酮更好的抗真菌和抗菌活性。然而，所有的吲唑衍生物均显示出非常好的抗氧化活性，并且还发现一些具有抗菌活性。在筛选出的化合物中，发现有15种最有效作为抗真菌剂（相对于立枯丝核菌，LC 50  = 2.36μgmL -1），发现15b是最具活性的抗菌剂（针对肺炎克雷伯菌，MIC = 24.68μgmL -1），而14b则是最具活性的抗氧化剂（IC 50  = 19.81μgmL -1）。
• Synthesis of new indazole derivatives as potential antioxidant agents
  作者：Majal Sapnakumari、Badiadka Narayana、Balladka Kunhanna Sarojini、Leelavathi Narayana Madhu

  DOI：10.1007/s00044-013-0835-6

  日期：2014.5

  New indazole derivatives were synthesized by reacting hydrazine hydrate and its derivatives with cyclohexenone derivatives, which in turn prepared from respective chalcones. The chemical structure of newly synthesized compounds was well characterized by using H-1 NMR, C-13 NMR, IR and mass spectral data. All the synthesized products were screened for their antioxidant properties. All indazole derivatives exhibited noticeable DPPH radical scavenging activity, reducing power capacity and total antioxidant capacity in comparison with the respective standards.
• Synthesis, structure–activity relationship and molecular docking of cyclohexenone based analogous as potent non-nucleoside reverse-transcriptase inhibitors
  作者：Muhammad Faizan Nazar、Muhammad Imran Abdullah、Amir Badshah、Asif Mahmood、Usman Ali Rana、Salah Ud-Din Khan

  DOI：10.1016/j.molstruc.2014.12.090

  日期：2015.4

  core in compounds is advantageously chosen effective synthons, which offer exciting perspectives in biological and pharmacological research. The present study reports the successful development of eight new cyclohexenone based anti-reverse transcriptase analogous using rational drug design synthesis principles. These new cyclohexenone derivatives (CDs) were synthesized by following a convenient route

  摘要 化合物中的查耳酮核心是有利地选择有效的合成子，这为生物学和药理学研究提供了令人兴奋的前景。本研究报告使用合理的药物设计合成原则成功开发了八种新的基于环己烯酮的抗逆转录酶类似物。这些新的环己烯酮衍生物 (CDs) 是按照方便的 Robinson 环化路线合成的，这些 CDs 的分子结构后来通过 1 H NMR、13 C NMR、FT-IR、UV-Vis 光谱等各种分析技术证实和质谱。所有合成的化合物都针对逆转录酶 (RT) 进行了理论和实验筛选，并发现了具有潜在活性的逆转录酶 (RT) 抑制剂。在研究的化合物中，化合物 2FC4 在非核苷结合位点显示出与 RT 的高相互作用，分别贡献高自由结合能 (Δ G -8.01 Kcal) 和 IC 50 (0.207 μg/ml)。进一步的结果表明，与其他化合物相比，带有更多卤素基团的化合物具有额外的疏水性，具有更好的抗逆转录酶活性。预计本研究
• Synthesis, Characterization and Crystal Structure of Ethyl 2-amino-4-(4-fluorophenyl)-6-phenylcyclohexa-1,3-diene-1-carboxylate
  作者：M. Sapnakumari、B. Narayana、K. Divya、K. Singh、S. Anthal、V. K. Gupta、R. Kant

  DOI：10.1080/15421406.2014.885348

  日期：2014.12.12

  Ethyl 2-amino-4-(4-fluorophenyl)-6-phenylcyclohexa-1,3-diene-1-carboxylate was synthesized from ethyl 6-(4-bromophenyl)-4-(4-fluorophenyl)-2-oxocyclohex-3-ene-1-carboxylate and ammonium acetate in glacial acetic acid. The synthesized compound was characterized by elemental analysis, FT-IR, thermogravimetric analysis (TGA), differential thermal analysis (DTA), UV-Visible, and single-crystal X-ray diffraction. The title compound, ethyl 2-amino-4-(4-fluorophenyl)-6-phenylcyclohexa-1,3-diene-1-carboxylate, C21H2OFNO2, crystallizes in the orthorhombic space group Pbca with the following unit-cell parameters: a = 17.417(2), b = 9.7287(9), c = 21.014(2) angstrom, and Z = 8. The crystal structure was solved by direct methods using single-crystal X-ray diffraction data collected at room temperature and refined by full-matrix least-squares procedures to a final R-value of 0.0644 for 1616 observed reflections. An intramolecular N-H horizontal ellipsis O hydrogen bond generates an S(6) graph-set motif. In the crystal, molecules are linked by N-H horizontal ellipsis O hydrogen bonds, forming a two-dimensional network.