ethyl 6-(4-methoxyphenyl)-4-(3-nitrophenyl)-2-oxocyclohex-3-enecarboxylate | 1097646-29-1

• 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 6-(4-methoxyphenyl)-4-(3-nitrophenyl)-2-oxocyclohex-3-enecarboxylate
• 英文别名: [3-[4-Ethoxycarbonyl-5-(4-methoxyphenyl)-3-oxo-cyclohexen-1-yl]phenyl]azinic acid；ethyl 6-(4-methoxyphenyl)-4-(3-nitrophenyl)-2-oxocyclohex-3-ene-1-carboxylate
• CAS: 1097646-29-1
• 化学式: C₂₂H₂₁NO₆
• 分子量: 395.412
• InChiKey: BQCLUZGGYPGCQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  98.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 6-(4-methoxyphenyl)-4-(3-nitrophenyl)-2-oxocyclohex-3-enecarboxylate 在 一水合肼 作用下， 以 甲醇 为溶剂， 以68%的产率得到4,5-dihydro-4-(4-methoxyphenyl)-6-(3-nitrophenyl)-2H-indazol-3-ol
  参考文献：
  名称：

  Synthesis and characterization of 4,6-diaryl-4,5-dihydro-2H-indazol-3-ols and 4,6-diaryl-2-phenyl-4,5-dihydro-2H-indazol-3-ols — a new series of fused indazole derivatives

  摘要：

  A novel class of 4,6-diaryl-4,5-dihydro-2H-indazol-3-ols and 4,6-diaryl-2-phenyl-4,5-dihydro-2H-indazol-3-ols is synthesized and characterized by melting point, elemental analysis, MS, FT-IR, H-1 and C-13 NMR, D2O exchanged H-1 NMR, and two-dimensional HSQC spectra.

  DOI：

  10.1007/s10593-008-0137-y
• 作为产物：
  描述：

  间硝基苯乙酮 在 barium hydroxide 、 一水合肼 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 乙二醇 为溶剂， 生成 ethyl 6-(4-methoxyphenyl)-4-(3-nitrophenyl)-2-oxocyclohex-3-enecarboxylate
  参考文献：
  名称：

  Synthesis and evaluation of new chalcones, derived pyrazoline and cyclohexenone derivatives as potent antimicrobial, antitubercular and antileishmanial agents

  摘要：

  A series of chalcones (1-8) were prepared by Claisen-Schmidt condensation of 3-nitroacetophenone with various aldehydes. These chalcones on cyclization with hydrazine hydrate in the presence of glacial acetic acid, hydrazine hydrate in absolute ethanol and ethyl acetoacetate in the presence of barium hydroxide gave corresponding N-acetyl pyrazolines (9-16), N-unsubstituted pyrazolines (17-19) and cyclohexenone derivatives (20-22). All the synthesized compounds were evaluated for their in vitro antibacterial and antifungal activity by using broth microdilution method, and many compounds showed promising activity against various tested bacteria and fungi. Among various tested compounds, 16 and 19 exhibited strongest activities against Streptococcus pyogenes and Pseudomonas aeruginosa; both have MIC value of 25 mu g/mL, which is fourfold greater than the standard drug. Many compounds showed good activity against Candida albican. Analogs 11, 12, 15-17 and 19 displayed two- to fivefold greater activity against C. albican as compared to the standard drug. Results of antitubercular evaluation revealed that compounds 4 and 19 displayed strong antimycobacterial activity against H(37)Rv having MIC of 25 and 62.5 mu g/mL, respectively. All analogs were found to be inactive against Leishmania braziliensis except analogs 4 and 5 which exhibited strong leishmanicidal activity against Leishmania promastigotes with IC50 values of 9.3 and 8.9 mu g/mL, respectively.

  DOI：

  10.1007/s00044-013-0803-1