(E)-3-(4-bromophenyl)-1-(naphthalen-2-yl)prop-2-en-1-one | 104765-80-2

• 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)-3-(4-bromophenyl)-1-(naphthalen-2-yl)prop-2-en-1-one
• 英文别名: (2E)-1-(2-naphthyl)-3-(4-bromophenyl)-2-propen-1-one；3t-(4-bromo-phenyl)-1-[2]naphthyl-propenone；3t-(4-Brom-phenyl)-1-[2]naphthyl-propenon；(E)-3-(4-bromophenyl)-1-(2-naphthyl)prop-2-en-1-one；(E)-3-(4-bromophenyl)-1-naphthalen-2-ylprop-2-en-1-one
• CAS: 104765-80-2
• 化学式: C₁₉H₁₃BrO
• 分子量: 337.216
• InChiKey: KDMYGWILLOEVQB-KPKJPENVSA-N

物化性质

• 熔点：
  174 °C
• 沸点：
  487.2±37.0 °C(Predicted)
• 密度：
  1.404±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  21
• 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：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-3-(4-bromophenyl)-1-(naphthalen-2-yl)prop-2-en-1-one 在 溴 作用下， 生成 (2RS,3SR)-2,3-dibromo-3-(4-bromo-phenyl)-1-[2]naphthyl-propan-1-one
  参考文献：
  名称：

  THE REARRANGEMENT OF ARYL-SUBSTITUTED PROPYNES TO ALLENES¹

  摘要：

  DOI：

  10.1021/jo01137a023
• 作为产物：
  描述：

  对溴肉桂酸 、 2-(naphthalen-2-yl)-2-oxoacetic acid 在 sodium persulfate 、 potassium carbonate 、 silver nitrate 作用下， 以 水 为溶剂， 反应 24.0h， 以75%的产率得到(E)-3-(4-bromophenyl)-1-(naphthalen-2-yl)prop-2-en-1-one
  参考文献：
  名称：

  Silver-Catalyzed Double-Decarboxylative Cross-Coupling of α-Keto Acids with Cinnamic Acids in Water: A Strategy for the Preparation of Chalcones

  摘要：

  A silver-catalyzed double-decarboxylative protocol has been proposed for the construction of chalcone derivatives via cascade coupling of substituted alpha-keto acids with cinnamic acids under the mild aqueous conditions. The developed method for constructing C-C bonds via double-decarboxylative reactions is efficient, practical, and environmentally benign by using the readily available starting materials. It should provide a promising synthesis candidate for the formation of diverse and useful chalcone derivatives in the fields of synthetic and pharmaceutical chemistry.

  DOI：

  10.1021/jo502642n

文献信息

• Microwave-Assisted Convenient Synthesis of<i>α</i>,<i>β</i>-Unsaturated Esters and Ketones<i>via</i>Aldol-Adduct Elimination
  作者：Pathi Suman、Rayala Nageswara Rao、Bhimapaka China Raju

  DOI：10.1002/hlca.201200526

  日期：2013.8

  Various fluorinated 3‐oxo ester/1,3‐diketones were reacted with carbonyl compounds, in presence of piperidine and under microwave irradiation, to afford (E)‐α,β‐unsaturated esters and ketones in good yields. The systematic study reveals that the reaction proceeded through the formation of aldol adduct. The method provides a new and simple way for C,C bond formations.

  在哌啶存在下并在微波辐射下，将各种氟化的3-氧代酯/ 1,3-二酮与羰基化合物反应，得到高收率的（E）-α，β-不饱和酯和酮。系统研究表明反应是通过醛醇加合物的形成而进行的。该方法为C，C键的形成提供了一种新的简单方法。
• Synthesis, in vitro and in silico Studies of Naphthalene Pyrazoline Prop-2-en-1-one Derivatives
  作者：B. Prabha、C. Raja、S. Nathiya、M.R. Ezhilarasi

  DOI：10.14233/ajchem.2020.22654

  日期：——

  The synthesized new naphthalene pyrazoline prop-2-en-1-one derivatives (NDPP 1-8) were obtained by the Michael addition reaction of ethyl propanoate, hydrazine hydrate with NPD as a multicomponent scaffold. (E)-1-(naphthalen-3-yl)-3-phenylprop-2-en-1-one (NPD) was formed from 2-acetyl naphthalene and substituted aldehyde via Claisen-Schmidt condensation reaction. The NDPP skeleton structures were confirmed by infrared, 1H & 13C NMR spectral data and elemental analysis. The structure of NDPP compounds was subjected to molecular docking and ADME studies. The result of ADME prediction, compound NDPP 2, which contains electron withdrawing -Cl group has high drug-likeness value 4.21 than the compounds NDPP 4 and 7 which had electron donating CH3 and OCH3 group shows the drug-likeness value 2.62. The NDPP 2 also has high drug score 0.63 than NDPP 4 and NDPP 7 have drug score 0.60 and 0.69, respectively. Docking studies shows that compound NDPP 5 which also contain electron withdrawing NO2 group has good binding affinity value -8.8 Kcal/mol were docked with 1UAG protein. These compounds showed good drug-likeness value 2.25 and drug score 0.65. in vitro Studies have a high inhibition value for the same NO2 substituted derivative. All the compounds have higher binding affinity value than standards binding affinity value.

  合成的新萘吡唑丙烯酮衍生物（NDPP 1-8）是通过乙酸乙酯、水合肼与NPD的Michael加成反应得到的，NPD作为多组分支架。 （E）-1-（萘-3-基）-3-苯基丙烯酮（NPD）是通过2-乙酰基萘和取代醛经过Claisen-Schmidt缩合反应形成的。 通过红外、1H和13C NMR光谱数据以及元素分析确认了NDPP骨架结构。 NDPP化合物的结构经过了分子对接和ADME研究。 ADME预测结果显示，含有电子吸引性-Cl基团的化合物NDPP 2具有较高的药物相似性值4.21，而含有电子供体CH3和OCH3基团的化合物NDPP 4和7显示的药物相似性值为2.62。 NDPP 2的药物评分也较高，为0.63，而NDPP 4和NDPP 7的药物评分分别为0.60和0.69。 对接研究表明，含有电子吸引性NO2基团的化合物NDPP 5与1UAG蛋白对接具有良好的结合亲和力值-8.8Kcal/mol。 这些化合物显示出良好的药物相似性值2.25和药物评分0.65。 体外研究显示具有相同NO2取代衍生物的高抑制值。 所有化合物的结合亲和力值均高于标准结合亲和力值。
• Naphthylchalcones induce apoptosis and caspase activation in a leukemia cell line: The relationship between mitochondrial damage, oxidative stress, and cell death
  作者：Evelyn Winter、Louise Domeneghini Chiaradia、Clarissa A.S. de Cordova、Ricardo José Nunes、Rosendo Augusto Yunes、Tânia Beatriz Creczynski-Pasa

  DOI：10.1016/j.bmc.2010.09.025

  日期：2010.11

  In this study, we investigated the effects of 24 chalcone derivatives from 2-naphthylacetophenone toward a lymphoblastic leukemia cell line (L1210). Three compounds, called R7, R13, and R15, presented concentration- and time-dependent cytotoxicity and induced cellular death by apoptosis via mitochondrial injury and oxidative stress. The effects of these compounds appear to occur through different mechanisms because R13 and R7 induced a greater disturbance of mitochondrial potential, and all compounds induced disturbances of cellular ATP content and increased caspase-3 activity before cellular death. These compounds also interfered with antioxidant enzymes activities and GSH content through different mechanisms. (C) 2010 Elsevier Ltd. All rights reserved.
• Rajasekaran, K.; Gnanasekaran, C., Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 1986, vol. 25, # 1, p. 64 - 66
  作者：Rajasekaran, K.、Gnanasekaran, C.

  DOI：——

  日期：——
• Synthesis, spectral analysis and <i>in vitro</i> microbiological evaluation of novel ethyl 4-(naphthalen-2-yl)-2-oxo-6-arylcyclohex-3-enecarboxylates and 4,5-dihydro-6-(napthalen-2-yl)-4-aryl-2<i>H</i>-indazol-3-ols
  作者：V. Kanagarajan、J. Thanusu、M. Gopalakrishnan

  DOI：10.3109/14756361003689856

  日期：2011.2.1

  A series of ethyl 4-(naphthalen-2-yl)-2-oxo-6-arylcyclohex-3-enecarboxylates 8--14 and 4,5-dihydro-6-(naphthalen-2-yl)-4-aryl-2H-indazol-3-ols 15--21 were synthesised and characterised by their spectroscopic data. In vitro microbiological evaluations were carried out for all the newly synthesised compounds 8--21 against clinically isolated bacterial and fungal strains. Compounds 9, 12 and 20 against Staphylococcus aureus, 10, 12, 20 against beta beta-haemolytic streptococcus, 11, 17 against Bacillus subtilis, 12, 16 and 20 against Vibreo cholerae, 13, 16 against Escherichia coli, 13, 16, 18, 19 against Salmonella typhii, 12, 18 against Shigella flexneri, 10 against Salmonella typhii, 10, 13, 17, 18 against Aspergillus flavus, 12, 17, 21 against Aspergillus niger, 12, 15, 17, 18, 20 against Mucor, Rhizopus and Microsporeum gypsuem exhibit potent antimicrobial activity.