1-(1H-benzimidazol-2-yl)-3-(3,4-dimethoxyphenyl)-2-propen-1-one | 36998-75-1

• 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: 1-(1H-benzimidazol-2-yl)-3-(3,4-dimethoxyphenyl)-2-propen-1-one
• 英文别名: 2-(3,4-Dimethoxycinnamoyl)benzimidazol；1-(1H-benzoimidazol-2-yl)-3-(3,4-dimethoxy-phenyl)-propenone；1-(1H-benzimidazol-2-yl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one
• CAS: 36998-75-1
• 化学式: C₁₈H₁₆N₂O₃
• 分子量: 308.337
• InChiKey: FVKNDGFGOUVRKQ-UHFFFAOYSA-N

物化性质

• 熔点：
  212 °C(Solv: ethanol (64-17-5))
• 沸点：
  548.8±52.0 °C(Predicted)
• 密度：
  1.266±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  64.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-氯甲基-5-苯基-1,3,4-噁二唑 、 1-(1H-benzimidazol-2-yl)-3-(3,4-dimethoxyphenyl)-2-propen-1-one 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以81%的产率得到3-(3,4-dimethoxyphenyl)-1-{1-[(5-phenyl-1,3,4-oxadiazol-2-yl)methyl]-1H-benzimidazol-2-yl}-2-propen-1-one
  参考文献：
  名称：

  Synthesis, characterization, and antimicrobial activity of benzimidazole-derived chalcones containing 1,3,4-oxadiazole moiety

  摘要：

  A series of novel benzimidazole-derived chalcones containing the 1,3,4-oxadiazole moiety were synthesized and characterized by IR, H-1, C-13 NMR, and mass spectra and elemental analysis. The synthesized compounds were evaluated for their efficiency as antibacterial agents against two Gram-positive and Gram-negative strains of bacteria along with antifungal activity against three fungal species. Antibacterial activity revealed that tested compounds exhibited potent activity whereas some compounds exhibited moderate antifungal activity as compared to the standards.

  DOI：

  10.1007/s10593-015-1653-1
• 作为产物：
  描述：

  邻苯二胺 在 盐酸 、 potassium dichromate 、 硫酸 、 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 30.33h， 生成 1-(1H-benzimidazol-2-yl)-3-(3,4-dimethoxyphenyl)-2-propen-1-one
  参考文献：
  名称：

  一些新型的-3-（5-取代的苯并咪唑-2-基）-5-芳基异恶唑啉的合成与生物评价

  摘要：

  摘要通过1-（1 H-苯并咪唑-2-基）的缩合反应，以优异的收率合成了一系列新的3-（5-取代的苯并咪唑-2-基）-5-芳基异恶唑啉系列（6a – h）。在室温下用羟胺将-3-（取代的苯基）丙-2-烯-1-酮（5a – h）。这些1-（1 H-苯并咪唑-2-基）-3-（取代的苯基）丙-2-烯-1-酮（5a-h）是通过将2-乙酰基苯并咪唑（4a-d）与不同的芳族醛，它们是通过邻苯二胺（1a-d）与α-羟基丙酸2反应制得的2-（α-羟基）乙基苯并咪唑（3a-d）氧化而获得的。合成的化合物通过IR，1 H NMR和MS分析进行表征。

  DOI：

  10.1016/j.cclet.2010.06.017

文献信息

• Synthesis and biological evaluation of some novel-3-(5-substituted benzimidazol-2-yl)-5-arylisoxazolines
  作者：Vanga Malla Reddy、Kunduru Ravinder Reddy

  DOI：10.1016/j.cclet.2010.06.017

  日期：2010.10

  of 2-acetyl benzimidazoles ( 4a – d ) with different aromatic aldehydes, which in turn were obtained by the oxidation of 2-(α-hydroxy)ethyl benzimidazoles ( 3a – d ) prepared by the reaction of o -phenylenediamines ( 1a – d ) with α-hydroxy propionic acid 2 . The synthesized compounds were characterized by their IR, 1 H NMR and MS analyses. These compounds were screened for their antibacterial and antifungal

  摘要通过1-（1 H-苯并咪唑-2-基）的缩合反应，以优异的收率合成了一系列新的3-（5-取代的苯并咪唑-2-基）-5-芳基异恶唑啉系列（6a – h）。在室温下用羟胺将-3-（取代的苯基）丙-2-烯-1-酮（5a – h）。这些1-（1 H-苯并咪唑-2-基）-3-（取代的苯基）丙-2-烯-1-酮（5a-h）是通过将2-乙酰基苯并咪唑（4a-d）与不同的芳族醛，它们是通过邻苯二胺（1a-d）与α-羟基丙酸2反应制得的2-（α-羟基）乙基苯并咪唑（3a-d）氧化而获得的。合成的化合物通过IR，1 H NMR和MS分析进行表征。
• Vekariya; Khunt; Parikh, Journal of the Indian Chemical Society, 2002, vol. 79, # 12, p. 966 - 967
  作者：Vekariya、Khunt、Parikh

  DOI：——

  日期：——
• Rajora, Jayanti; Yadav, Janardan; Kumar, Ravindra, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2010, vol. 49, # 7, p. 989 - 993
  作者：Rajora, Jayanti、Yadav, Janardan、Kumar, Ravindra、Srivastava, Yogendra K.

  DOI：——

  日期：——
• Synthesis, characterization, and antimicrobial activity of benzimidazole-derived chalcones containing 1,3,4-oxadiazole moiety
  作者：Gangadhar A. Meshram、Vipul A. Vala

  DOI：10.1007/s10593-015-1653-1

  日期：2015.1

  A series of novel benzimidazole-derived chalcones containing the 1,3,4-oxadiazole moiety were synthesized and characterized by IR, H-1, C-13 NMR, and mass spectra and elemental analysis. The synthesized compounds were evaluated for their efficiency as antibacterial agents against two Gram-positive and Gram-negative strains of bacteria along with antifungal activity against three fungal species. Antibacterial activity revealed that tested compounds exhibited potent activity whereas some compounds exhibited moderate antifungal activity as compared to the standards.