(2E)-1-(4-acetylaminophenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-enone | 1440974-33-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (2E)-1-(4-acetylaminophenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-enone
• 英文别名: N-[4-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]phenyl]acetamide
• CAS: 1440974-33-3
• 化学式: C₂₀H₂₁NO₅
• 分子量: 355.39
• InChiKey: QGJNAGJAXOOUJA-BJMVGYQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2E)-1-(4-acetylaminophenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-enone 在 sodium acetate 、 一水合肼 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 2.3h， 以81%的产率得到3-(4-acetylaminophenyl)-5-(3,4,5-trimethoxyphenyl)-1H-pyrazoline
  参考文献：
  名称：

  Facile sonochemical synthesis of novel pyrazolyne derivates at ambient conditions

  摘要：

  Claisen-Schmidt condensation reaction of 4-acetamidoacetophenone with aromatic aldehydes under ultrasonic irradiation affords acetylaminochalcones (yields: 71-90%) which also under ultrasonic irradiation and in the presence of sodium acetate and acetic acid aqueous undergo facile and clean cyclocondensation with hydrazine to afford 3-(4-acetamidophenyl)-5-(aryl)-1-H-pyrazolines. The pyrazolines were obtained in good to excellent yields (81-89%), and were characterized by conventional spectral data. The work-up is simple and the results obtained indicate that, unlike classical heating, ultrasonic irradiation results in higher yields, shorter reaction times (1.5-2.3 h) and milder conditions. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ultsonch.2012.11.018
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲醛 、 4-乙酰胺苯乙酮 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.08h， 以83%的产率得到(2E)-1-(4-acetylaminophenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-enone
  参考文献：
  名称：

  Facile sonochemical synthesis of novel pyrazolyne derivates at ambient conditions

  摘要：

  Claisen-Schmidt condensation reaction of 4-acetamidoacetophenone with aromatic aldehydes under ultrasonic irradiation affords acetylaminochalcones (yields: 71-90%) which also under ultrasonic irradiation and in the presence of sodium acetate and acetic acid aqueous undergo facile and clean cyclocondensation with hydrazine to afford 3-(4-acetamidophenyl)-5-(aryl)-1-H-pyrazolines. The pyrazolines were obtained in good to excellent yields (81-89%), and were characterized by conventional spectral data. The work-up is simple and the results obtained indicate that, unlike classical heating, ultrasonic irradiation results in higher yields, shorter reaction times (1.5-2.3 h) and milder conditions. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ultsonch.2012.11.018

文献信息

• <i>N</i>-(4-((E)-3-Arylacryloyl)phenyl)acetamide Derivatives and their Antileishmanial Activity
  作者：Dency J. Pacheco、Jorge Trilleras、Jairo Quiroga、Jennifer Gutiérrez、Luis Prent、Tobinson Coavas、Juan C. Marín、Gabriela Delgado

  DOI：10.5935/0103-5053.20130203

  日期：——

  The antileishmanial activity of a series of enonic derivatives (chalcones) synthesized via Claisen-Schmidt condensation reactions assisted by ultrasonic radiation was characterized by analyzing their cytotoxicity against Leishmania (Viannia) panamensis promastigotes, a species responsible for over 90% of Leishmania cases in Colombia. Two compounds were active against Leishmania with selectivity indexes of LC50 EC50-1 (lethal concentration 50 and effective concentration 50) higher than 27 and 3, respectively. These results suggest that a substitution on one of the two chalcone rings (aromatic ring A) with oxygen is convenient. Compound 3g should be further investigated for its antileishmanial activity, especially for being easy to obtain in high yields, making it possible to produce drugs for the treatment of cutaneous leishmaniasis.