1-(1-苯并呋喃-2-基)-3-(4-羟基苯基)丙-2-烯-1-酮 | 93327-89-0

• 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
• 中文名称: 1-(1-苯并呋喃-2-基)-3-(4-羟基苯基)丙-2-烯-1-酮
• 英文名称: 1--2-<4-hydroxy-phenyl>-ethylen
• 英文别名: 1-benzofuran-2-yl-3-(4-hydroxy-phenyl)-propenone；1-(1-Benzofuran-2-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one；1-(1-benzofuran-2-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one
• CAS: 93327-89-0
• 化学式: C₁₇H₁₂O₃
• 分子量: 264.28
• InChiKey: RHWZEVMRPSKGBE-UHFFFAOYSA-N

物化性质

• 熔点：
  244 °C(Solv: isopropanol (67-63-0))
• 沸点：
  450.9±45.0 °C(Predicted)
• 密度：
  1.288±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(1-苯并呋喃-2-基)-3-(4-羟基苯基)丙-2-烯-1-酮 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以76%的产率得到3-(benzofuran-2-yl)-5-(4-hydroxyphenyl)-2-pyrazoline
  参考文献：
  名称：

  3-(Substituted Aryl)-1-benzofuranyl-2-propenones: Antimicrobial Properties of Some Chalcones-Type Compounds and their 2-Pyrazoline Derivatives

  摘要：

  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。

  DOI：

  10.1155/2011/806854
• 作为产物：
  描述：

  2-乙酰基苯并呋喃 、 对羟基苯甲醛 在 potassium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 130.0 ℃ 、1.0 MPa 条件下， 反应 0.17h， 生成 1-(1-苯并呋喃-2-基)-3-(4-羟基苯基)丙-2-烯-1-酮
  参考文献：
  名称：

  Design, synthesis, and antitubercular evaluation of novel series of 3-benzofuran-5-aryl-1-pyrazolyl-pyridylmethanone and 3-benzofuran-5-aryl-1-pyrazolylcarbonyl-4-oxo-naphthyridin analogs

  摘要：

  Twenty-eight newer 3-benzofuran-5-aryl-1-pyrazolyl-pyridylmethanone and 3-benzofuran-5-aryl-1-pyrazolylcarbonyl-4-oxo-naphthyridin analogs were synthesized by microwave irradiation method and evaluated for in-vitro and in-vivo antitubercular activity against multidrug-resistant M. tuberculosis stains. Structure activity relationship study was carried out and found NO2 (o) substituted 3-benzo-furan-5-aryl-1-pyrazolylcarbonyl-4-oxo-naphthyridin was most potent antitubercular agent against M. tuberculosis, even better than standard drug isoniazid and comparable with rifampin. Other synthesized compounds 7j, 7f, 7a, 7e and 5d, 5f were found moderate to good activity in in-vitro model at lower IC50 values 85 mu M, 154 mu M, 157 mu M, 164 mu M, 170 mu M and 190 mu ML respectively. In in-vivo animal model compound 7j was drastically reduced the bacterial load in lung and spleen tissues at the dose of 25 mg/kg body weight. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.05.035

文献信息

• Jadhav; Choudhari; Patil, Asian Journal of Chemistry, 2010, vol. 22, # 7, p. 5443 - 5446
  作者：Jadhav、Choudhari、Patil、Shinde

  DOI：——

  日期：——
• Design, synthesis, and antitubercular evaluation of novel series of 3-benzofuran-5-aryl-1-pyrazolyl-pyridylmethanone and 3-benzofuran-5-aryl-1-pyrazolylcarbonyl-4-oxo-naphthyridin analogs
  作者：Kuntal Manna、Yadvendra K. Agrawal

  DOI：10.1016/j.ejmech.2010.05.035

  日期：2010.9

  Twenty-eight newer 3-benzofuran-5-aryl-1-pyrazolyl-pyridylmethanone and 3-benzofuran-5-aryl-1-pyrazolylcarbonyl-4-oxo-naphthyridin analogs were synthesized by microwave irradiation method and evaluated for in-vitro and in-vivo antitubercular activity against multidrug-resistant M. tuberculosis stains. Structure activity relationship study was carried out and found NO2 (o) substituted 3-benzo-furan-5-aryl-1-pyrazolylcarbonyl-4-oxo-naphthyridin was most potent antitubercular agent against M. tuberculosis, even better than standard drug isoniazid and comparable with rifampin. Other synthesized compounds 7j, 7f, 7a, 7e and 5d, 5f were found moderate to good activity in in-vitro model at lower IC50 values 85 mu M, 154 mu M, 157 mu M, 164 mu M, 170 mu M and 190 mu ML respectively. In in-vivo animal model compound 7j was drastically reduced the bacterial load in lung and spleen tissues at the dose of 25 mg/kg body weight. (C) 2010 Elsevier Masson SAS. All rights reserved.
• 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。