4-(3-(benzofuran-2-yl)-4,5-dihydro-1H-pyrazol-5-yl)-2-methoxyphenol | 1356936-60-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-(3-(benzofuran-2-yl)-4,5-dihydro-1H-pyrazol-5-yl)-2-methoxyphenol
• 英文别名: 3-(benzofuran-2-yl)-5-(3-methoxy-4-hydroxyphenyl)-2-pyrazoline；4-[3-(1-benzofuran-2-yl)-4,5-dihydro-1H-pyrazol-5-yl]-2-methoxyphenol
• CAS: 1356936-60-1
• 化学式: C₁₈H₁₆N₂O₃
• 分子量: 308.337
• InChiKey: FWODPVWVLLAJRM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  67
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(3-(benzofuran-2-yl)-4,5-dihydro-1H-pyrazol-5-yl)-2-methoxyphenol 在 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 3-(benzofuran-2-yl)-5-(4-hydroxy-3-methoxyphenyl)-N-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazole-1-carboxamide
  参考文献：
  名称：

  Synthesis of benzofuran based 1,3,5-substituted pyrazole derivatives: As a new class of potent antioxidants and antimicrobials-A novel accost to amend biocompatibility

  摘要：

  In search for a new antioxidant and antimicrobial agent with improved potency, we synthesized a series of benzofuran based 1,3,5-substituted pyrazole analogues (5a-l) in five step reaction. Initially, o-alkyl derivative of salicyaldehyde readily furnish corresponding 2-acetyl benzofuran 2 in good yield, on treatment with 1,8-diaza bicyclo[5.4.0]undec-7-ene (DBU) in the presence of molecular sieves. Further, aldol condensation with vanillin, Claisen-Schmidt condensation reaction with hydrazine hydrate followed by coupling of substituted anilines afforded target compounds. The structures of newly synthesized compounds were confirmed by IR, H-1 NMR, C-13 NMR, mass, elemental analysis and further screened for their antioxidant and antimicrobial activities. Among the tested compounds 5d and 5f exhibited good antioxidant property with 50% inhibitory concentration higher than that of reference while compounds 5h and 5l exhibited good antimicrobial activity at concentration 1.0 and 0.5 mg/mL compared with standard, streptomycin and fluconazole respectively. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.061
• 作为产物：
  描述：

  水杨醛 在 ClZr₄ 、 一水合肼 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 10.0h， 生成 4-(3-(benzofuran-2-yl)-4,5-dihydro-1H-pyrazol-5-yl)-2-methoxyphenol
  参考文献：
  名称：

  Synthesis of benzofuran based 1,3,5-substituted pyrazole derivatives: As a new class of potent antioxidants and antimicrobials-A novel accost to amend biocompatibility

  摘要：

  In search for a new antioxidant and antimicrobial agent with improved potency, we synthesized a series of benzofuran based 1,3,5-substituted pyrazole analogues (5a-l) in five step reaction. Initially, o-alkyl derivative of salicyaldehyde readily furnish corresponding 2-acetyl benzofuran 2 in good yield, on treatment with 1,8-diaza bicyclo[5.4.0]undec-7-ene (DBU) in the presence of molecular sieves. Further, aldol condensation with vanillin, Claisen-Schmidt condensation reaction with hydrazine hydrate followed by coupling of substituted anilines afforded target compounds. The structures of newly synthesized compounds were confirmed by IR, H-1 NMR, C-13 NMR, mass, elemental analysis and further screened for their antioxidant and antimicrobial activities. Among the tested compounds 5d and 5f exhibited good antioxidant property with 50% inhibitory concentration higher than that of reference while compounds 5h and 5l exhibited good antimicrobial activity at concentration 1.0 and 0.5 mg/mL compared with standard, streptomycin and fluconazole respectively. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.061

文献信息

• 3-(Substituted Aryl)-1-benzofuranyl-2-propenones: Antimicrobial Properties of Some Chalcones-Type Compounds and their 2-Pyrazoline Derivatives
  作者：Demet Coskun、Misir Ahmedzade、Sevda Kirbag

  DOI：10.1155/2011/806854

  日期：——

  2-Acetylbenzofuran on condensation with furan-2-carboxaldehyde and pyrrole-2-carboxaldehyde in methanolic KOH solution yielded the corresponding benzofuran chalcones. These two compounds and nine benzofuran chalcones were synthesized before, were further reacted with hydrazine hydrate in ethanol which led to the formation of 2-pyrazoline derivatives. All the synthesized compounds were characterized by elemental analysis, melting point determination, infrared spectroscopy and nuclear magnetic resonance spectroscopy. Nine chalcone-type compounds and eleven 2-pyrazolines were evaluated for their biological activities against the six bacteria and the three yeast and it was seen that thirteen compounds showed activity. Four of them are chalcone-type compounds showed more or less activity.

  在甲醇性氢氧化钾溶液中，2-乙酰基苯并呋喃与呋喃-2-甲醛和吡咯-2-甲醛缩合，生成相应的苯并呋喃香豆素。这两种化合物和之前合成的九种苯并呋喃香豆素进一步与乙醇中的水合肼反应，形成2-吡唑啉衍生物。所有合成的化合物均通过元素分析、熔点测定、红外光谱和核磁共振光谱进行表征。对九种香豆素类化合物和十一种2-吡唑啉进行了对六种细菌和三种酵母的生物活性评估，发现十三种化合物表现出活性，其中四种是香豆素类化合物表现出不同程度的活性。
• Synthesis of some acylated 2-pyrazoline and chalcone derivatives
  作者：Demet Coşkun、Misir Ahmedzade

  DOI：10.1007/s11164-013-1032-4

  日期：2014.3

  α-Haloesters containing the chalcone structure and α-haloamides containing the pyrazoline ring have been synthesized by reaction of substituted hydroxy chalcones and pyrazoline derivatives (prepared as reported elsewhere; J Chem 8(4):1574–1581, 2011) with chloroacetyl chloride in dry THF in the presence of Et3N. The structures of the synthesized compounds were confirmed by IR, 1H NMR, and (for some compounds) 13C NMR spectroscopy.

  含有查尔酮结构的 α 卤化酯和含有吡唑啉环的 α 卤化酰胺是通过取代的羟基查尔酮和吡唑啉衍生物（制备方法见其他报道；J Chem 8(4):1574-1581, 2011）与氯乙酰氯在有 Et3N 存在的干燥 THF 中反应合成的。合成化合物的结构通过红外光谱、1H NMR 和（某些化合物的）13C NMR 光谱得到了证实。
• Synthesis of benzofuran based 1,3,5-substituted pyrazole derivatives: As a new class of potent antioxidants and antimicrobials-A novel accost to amend biocompatibility
  作者：Javarappa Rangaswamy、Honnaiah Vijay Kumar、Salakatte Thammaiah Harini、Nagaraja Naik

  DOI：10.1016/j.bmcl.2012.05.061

  日期：2012.7

  In search for a new antioxidant and antimicrobial agent with improved potency, we synthesized a series of benzofuran based 1,3,5-substituted pyrazole analogues (5a-l) in five step reaction. Initially, o-alkyl derivative of salicyaldehyde readily furnish corresponding 2-acetyl benzofuran 2 in good yield, on treatment with 1,8-diaza bicyclo[5.4.0]undec-7-ene (DBU) in the presence of molecular sieves. Further, aldol condensation with vanillin, Claisen-Schmidt condensation reaction with hydrazine hydrate followed by coupling of substituted anilines afforded target compounds. The structures of newly synthesized compounds were confirmed by IR, H-1 NMR, C-13 NMR, mass, elemental analysis and further screened for their antioxidant and antimicrobial activities. Among the tested compounds 5d and 5f exhibited good antioxidant property with 50% inhibitory concentration higher than that of reference while compounds 5h and 5l exhibited good antimicrobial activity at concentration 1.0 and 0.5 mg/mL compared with standard, streptomycin and fluconazole respectively. (C) 2012 Elsevier Ltd. All rights reserved.