(E)-1-(2-aminophenyl)-3-(4-fluorophenyl)prop-2-en-1-one | 156492-25-0

• 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: (E)-1-(2-aminophenyl)-3-(4-fluorophenyl)prop-2-en-1-one
• 英文别名: 1-(2-Aminophenyl)-3-(4-fluorophenyl)prop-2-en-1-one
• CAS: 156492-25-0
• 化学式: C₁₅H₁₂FNO
• 分子量: 241.265
• InChiKey: CZJFULGWNDORMG-JXMROGBWSA-N

物化性质

• 沸点：
  409.5±45.0 °C(Predicted)
• 密度：
  1.228±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-1-(2-aminophenyl)-3-(4-fluorophenyl)prop-2-en-1-one 在 sodium dodecyl-sulfate 、 对甲苯磺酸 作用下， 以 水 为溶剂， 反应 4.0h， 以66%的产率得到
  参考文献：
  名称：

  p -TsOH促进的的（合成ë）-6-苯基-7-苯乙烯基-5,6-二氢二苯并[ b，ħ ] [1,6]萘啶经由级联分子内氮杂-迈克尔加成/弗里德兰德2'-aminochalcones缩合在SDS / H 2 O系统中†

  摘要：

  布朗斯台德酸促进的新型（E）-6-苯基-7-苯乙烯基-5,6-二氢二苯并[ b，h ] [1,6]萘啶的级联合成通过使用十二烷基硫酸钠对2'-氨基查耳酮进行均二聚而实现（SDS）作为水中的表面活性剂。除了水是对环境无害的反应介质之外，在连续的一锅操作方案下，该反应可在高原子经济的条件下顺利进行。

  DOI：

  10.1039/c6ra04837d
• 作为产物：
  描述：

  (E)-3-(4-fluorophenyl)-1-(2-nitrophenyl)prop-2-en-1-one 在 氢气 、 magnesium oxide 作用下， 以 邻二甲苯 为溶剂， 70.0 ℃ 、900.01 kPa 条件下， 反应 0.75h， 以65%的产率得到(E)-1-(2-aminophenyl)-3-(4-fluorophenyl)prop-2-en-1-one
  参考文献：
  名称：

  Process Intensification with Bifunctional Heterogeneous Catalysts: Selective One-Pot Synthesis of 2′-Aminochalcones

  摘要：

  2'-Aminochalcones of pharmaceutical and commercial interest have been obtained in high yields and selectivities through a one-pot process using a bifunctional heterogeneous catalyst bearing base and metal active sites. This is a physical mixture material formed by a high-surface-area MgO and Pt on TiO2. The process involves as the first step the Claisen-Schmidt condensation between o-nitroacetophenone and benzaldehyde derivatives on the basic catalytic function. This is followed by a chemoselective hydrogenation of the nitro group in the presence of the carbonyl and double-bond carbon carbon groups within the molecule. Using the bifunctional catalyst and the reaction system proposed here, it is possible to produce, under mild reaction conditions and short reaction times, 2'-aminochalcones with higher yields and selectivities than those obtained by conventional multistep methods.

  DOI：

  10.1021/cs5011713

文献信息

• Nazarov cyclization of 1,4-pentadien-3-ols: preparation of cyclopenta[b]indoles and spiro[indene-1,4′-quinoline]s
  作者：Zhiming Wang、Xingzhu Xu、Zhanshou Gu、Wei Feng、Houjun Qian、Zhengyi Li、Xiaoqiang Sun、Ohyun Kwon

  DOI：10.1039/c5cc08596a

  日期：——

  The first Lewis acid-catalyzed intramolecular interrupted Nazarov cyclization of 1,4-pentadien-3-ols is described.

  第一个由Lewis酸催化的1,4-戊二烯-3-醇分子内中断的Nazarov环化反应被描述了。
• Synthesis of 3-Substituted 2,1-Benzisoxazoles by the Oxidative Cyclization of 2-Aminoacylbenzenes with Oxone
  作者：Antonio Arcadi、Marco Chiarini、Luana Del Vecchio、Fabio Marinelli、Leucio Rossi

  DOI：10.1055/s-0035-1561471

  日期：——

  An efficient approach to the synthesis of 2,1-benzisoxazoles through direct construction of the N–O bond by the chemoselective oxidation of 2-aminoacylbenzenes with Oxone is described. This alternative methodology is characterized by its simple and transition-metal-free conditions and good functional group compatibility utilizing Oxone as a green oxidant instead of hypervalent iodine compounds. Moreover

  摘要 描述了一种通过2-氧酰基苯与Oxone的化学选择性氧化直接构建N-O键来合成2,1-苯并恶唑的有效方法。这种替代方法的特点是其简单且无过渡金属的条件，并且利用Oxone作为绿色氧化剂代替高价碘化合物，具有良好的官能团相容性。而且，通过避免使用2-叠氮基取代的芳基酮，与先前报道的方法相比，该新方法简化了步骤数。 描述了一种通过2-氧酰基苯与Oxone的化学选择性氧化直接构建N-O键来合成2,1-苯并恶唑的有效方法。这种替代方法的特点是其简单且无过渡金属的条件，并且利用Oxone作为绿色氧化剂代替高价碘化合物，具有良好的官能团相容性。而且，通过避免使用2-叠氮基取代的芳基酮，与先前报道的方法相比，该新方法简化了步骤数。
• Synthesis and cdc25B inhibitory activity evaluation of chalcones
  作者：Fei Zhao、Qing-Jie Zhao、Jing-Xia Zhao、Da-Zhi Zhang、Qiu-Ye Wu、Yong-Sheng Jin

  DOI：10.1007/s10600-013-0563-7

  日期：2013.5

  A library of sixty-five chalcones was prepared for screening against the protein phosphatase, cdc25B. From this library, thirteen compounds were found having good inhibitory activity. Two compounds have excellent activity and can be used for the design of more potent antiproliferative agents.

  制备了一个包含六十五种查尔酮的库，用于针对蛋白磷酸酶cdc25B进行筛选。从这个库中，发现了十三种具有良好抑制活性的化合物。其中两种化合物表现出极佳的活性，可用于设计更有效的抗增殖剂。
• Synthesis and biological evaluation of a new series of 4-alkoxy-2-arylquinoline derivatives as potential antituberculosis agents
  作者：Gonca TOSUN、Tayfun ARSLAN、Zeynep İSKEFİYELİ、Murat KÜÇÜK、Şengül ALPAY KARAOĞLU、Nurettin YAYLI

  DOI：10.3906/kim-1501-112

  日期：——

  Three new series of 33 quinolone compounds, 2-(2-, 3-, and 4-fluorophenyl)-4-O-alkyl(C$_5-15})$quinolines (7a-k, 8a-k, and 9a-k), were synthesized from 2-(2-, 3-, and 4-fluorophenyl)-2,3-dihydroquinolin-4(1H)-one (4, 5, and 6) by the reaction of alkyl halides under basic conditions in DMF. The new compounds 7a-k, 8a-k, and 9a-k were synthesized from flavonones 4-6, which can be considered new precursors for quinoline synthesis through a one-step reaction. All the target compounds (7a-k, 8a-k, and 9a-k) were evaluated for their in vitro antimicrobial activity against nine test microorganisms. They showed the most activity against Mycobacterium smegmatis with minimum inhibitory concentrations (MIC) of 62.5-500 $\mu $g/mL, indicating their potential uses as antituberculosis agents. Among them 8a-k (m-fluoride) were the most active compounds against M. smegmatis (MIC, 62.5-125 $\mu $g/mL). The newly synthesized title compounds were also evaluated for their in vitro antioxidant activities using DPPH• radical scavenging and FRAP tests. They showed at a low concentration (mg/mL) a range of SC$_50}$ values of 0.03-12.48 mg/mL (DPPH•) and 0-722 $\mu $M (FRAP), respectively. The antioxidant results of compounds 7a-k, 8a-k, and 9a-k revealed that the length of the alkyl chain was negatively correlated with antioxidant capacity.

  合成了3个系列共33种喹诺酮化合物:2-(2-、3-和4-氟苯基)-4-O-烷基(C$_5-15}$)喹诺啉(7a-k、8a-k和9a-k),由2-(2-、3-和4-氟苯基)-2,3-二氢喹啉-4(1H)-酮(4、5和6)在DMF中用卤代烷在碱性条件下反应制得。新化合物7a-k、8a-k和9a-k由黄酮酮4-6制备,可视为一步反应合成喹诺啉的新前体。所有目标化合物(7a-k、8a-k和9a-k)均对其体外抗菌活性进行了评价,在九种试验微生物中它们对耻垢分枝杆菌的活性最强,最高抑制浓度(MIC)为62.5-500 $\mu g/ mL,表明它们有可能用作抗结核剂。其中8a-k(间氟苯基)对耻垢分枝杆菌的活性最强(MIC, 62.5-125 $\mu g/ mL)。新合成的标题化合物也用DPPH•自由基清除法和FRAP法对其体外抗氧化活性进行了评价。它们在低浓度(mg/mL)下的SC$_50}$值范围分别为0.03-12.48 mg/mL(DPPH•)和0-722 $\mu M$(FRAP)。化合物7a-k、8a-k和9a-k的抗氧化结果表明,烷基链的长度与抗氧化能力负相关。
• Straightforward Synthesis of Novel 4-Styrylquinolines/4-Styrylquinolin-2-ones and 9-Styryldihydroacridin-1(2H)-ones from Substituted 2′-Aminochalcones
  作者：Alirio Palma、Angie Meléndez、Esteban Plata、Diego Rodríguez、Diana Ardila、Sergio A. Guerrero、Lina M. Acosta、Justo Cobo、Manuel Nogueras

  DOI：10.1055/s-0039-1707985

  日期：2020.6

  approach, new series of these compounds were straightforwardly synthesized in high yields starting from synthetically available 2′-aminochalcones and 1,3-dicarbonyl compounds in glacial acetic acid as a catalyst via the Friedländer reaction. Our approach also offers an expeditious way to access novel molecular hybrids in whose structures styryl and chalcone fragments are attached at the C4 and C3 positions

  描述了开发多取代的4-苯乙烯基喹啉/ 4-苯乙烯基喹啉-2-酮和9-苯乙烯基二氢ac啶酮-1-酮的小文库的另一种有效的一步方法。根据这种方法，这些新化合物系列是直接从弗里德兰德反应中以冰乙酸为催化剂的合成的2'-氨基查耳酮和1,3-二羰基化合物开始以高收率直接合成的。我们的方法还提供了一种访问新型分子杂化物的快捷方法，在这种杂物中，苯乙烯基和查耳酮片段的结构分别连接在喹啉环的C4和C3位置。所有合成的化合物均通过IR，HRMS和NMR技术进行了充分表征，并且大多数化合物已在美国国家癌症研究所进行了抗肿瘤活性筛选。