(E)-1-(benzofuran-2-yl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-1-(benzofuran-2-yl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one
• 英文别名: 3-(3-methoxy-4-hydroxyphenyl)-1-(benzofuran-2-yl)-2-propen-1-one；1-benzofuran-2-yl-3t-(4-hydroxy-3-methoxy-phenyl)-propenone；1-Benzofuran-2-yl-3t-(4-hydroxy-3-methoxy-phenyl)-propenon；(E)-1-(1-benzofuran-2-yl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one
• 化学式: C₁₈H₁₄O₄
• 分子量: 294.307
• InChiKey: GMFQJEFJCDWEFW-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-1-(benzofuran-2-yl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以83%的产率得到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
• 作为产物：
  描述：

  水杨醛 在 potassium tert-butylate 、 氯化锆(IV) 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (E)-1-(benzofuran-2-yl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  磺酰氯偶联的新型苯并呋喃聚集的C-2,4,6-取代的嘧啶衍生物的合成：口服生物有效，选择性，有效的抗氧化剂和抗菌药物候选物

  摘要：

  在本研究中，我们已努力开发具有增强功效的新型合成抗氧化剂和抗菌剂。新型的苯并呋喃聚集的C -2,4,6-取代的嘧啶衍生物5a，5b，5c，5d，5e，5f，6a，6b，6c，6d，6e，6f，7a，7b，7c，7d，7e，7f，8a，8b，8c，8D，8E，8F，图9a，图9b，图9c，图9d，图9e，9f中通过简单和有效的四步反应途径进行合成。最初，经叔碳酸钾处理后，水杨醛的o-烷基衍生物很容易以高收率提供相应的2-乙酰基苯并呋喃2。分子筛存在下的丁醇盐。此外，通过硫脲处理，克莱森-施密特与芳族醛缩合，然后与不同的磺酰氯偶联反应，得到目标化合物。通过IR，1 H NMR，13 C NMR，质量和元素分析确认了新合成的化合物的结构，并进一步筛选了它们的抗氧化剂和抗菌活性。结果表明，合成的化合物8b，8e，9b和9e产生了显着的抗氧化活性，抑制浓度比参考浓度高50％，而化合物7d和7c 与庆大霉素和制霉菌素相比，它们在1

  DOI：

  10.1002/jhet.2209

文献信息

• 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。
• Polonovski et al., Bulletin de la Societe Chimique de France, 1953, p. 200,202
  作者：Polonovski et al.

  DOI：——

  日期：——
• 3-(Substituted Aryl)-1-(benzofuran-2-yl)-2-propenones, Part 1: Synthesis and Characterization of Some Novel Chalcones
  作者：Demet Coşkun、Misir Ahmedzade

  DOI：10.1080/00397910802178997

  日期：2008.10.22

  Synthesis and characterization of some novel chalcones by condensation of 2-acetylbenzofurane and various aromatic aldehydes is described.
• 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.
• Synthesis of Novel Benzofuran-Gathered<i>C</i>-2,4,6-substituted Pyrimidine Derivatives Conjugated by Sulfonyl Chlorides: Orally Bioavailable, Selective, Effective Antioxidants and Antimicrobials Drug Candidates
  作者：Javarappa Rangaswamy、Honnaiah Vijay Kumar、Salakatte Thammaiah Harini、Nagaraja Naik

  DOI：10.1002/jhet.2209

  日期：2015.9

  effort to develop the novel synthetic antioxidants and antimicrobials with improved potency. The novel benzofuran‐gathered C‐2,4,6‐substituted pyrimidine derivatives 5a, 5b, 5c, 5d, 5e, 5f, 6a, 6b, 6c, 6d, 6e, 6f, 7a, 7b, 7c, 7d, 7e, 7f, 8a, 8b, 8c, 8d, 8e, 8f, 9a, 9b, 9c, 9d, 9e, 9f were synthesized by simple and efficient four‐step reaction pathway. Initially, o‐alkyl derivative of salicylaldehyde readily

  在本研究中，我们已努力开发具有增强功效的新型合成抗氧化剂和抗菌剂。新型的苯并呋喃聚集的C -2,4,6-取代的嘧啶衍生物5a，5b，5c，5d，5e，5f，6a，6b，6c，6d，6e，6f，7a，7b，7c，7d，7e，7f，8a，8b，8c，8D，8E，8F，图9a，图9b，图9c，图9d，图9e，9f中通过简单和有效的四步反应途径进行合成。最初，经叔碳酸钾处理后，水杨醛的o-烷基衍生物很容易以高收率提供相应的2-乙酰基苯并呋喃2。分子筛存在下的丁醇盐。此外，通过硫脲处理，克莱森-施密特与芳族醛缩合，然后与不同的磺酰氯偶联反应，得到目标化合物。通过IR，1 H NMR，13 C NMR，质量和元素分析确认了新合成的化合物的结构，并进一步筛选了它们的抗氧化剂和抗菌活性。结果表明，合成的化合物8b，8e，9b和9e产生了显着的抗氧化活性，抑制浓度比参考浓度高50％，而化合物7d和7c 与庆大霉素和制霉菌素相比，它们在1