β-(4-chlorophenyl)-3,4-dimethylacrylophenone | 57077-29-9

• 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: β-(4-chlorophenyl)-3,4-dimethylacrylophenone
• 英文别名: 3-(4-Chlorophenyl)-1-(3,4-dimethylphenyl)prop-2-en-1-one
• CAS: 57077-29-9
• 化学式: C₁₇H₁₅ClO
• 分子量: 270.758
• InChiKey: FGSZXJPGPTURBI-UHFFFAOYSA-N

物化性质

• 沸点：
  435.6±45.0 °C(Predicted)
• 密度：
  1.155±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  β-(4-chlorophenyl)-3,4-dimethylacrylophenone 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以80%的产率得到5-(4-chlorophenyl)-3-(3,4-dimethylphenyl)-4,5-dihydro-1H-pyrazole
  参考文献：
  名称：

  El-Hashash, M. A.; Soliman, F. M. A.; Souka, L. M., Revue Roumaine de Chimie, 1995, vol. 40, # 1, p. 59 - 66

  摘要：

  DOI：
• 作为产物：
  描述：

  在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 β-(4-chlorophenyl)-3,4-dimethylacrylophenone
  参考文献：
  名称：

  Synthesis, biological evaluation and molecular modeling of dihydro-pyrazolyl-thiazolinone derivatives as potential COX-2 inhibitors

  摘要：

  A series of dihydro-pyrazolyl-thiazolinone derivatives (5a-5t) have been synthesized and their biological activities were also evaluated as potential cyclooxygenase-2 (COX-2) inhibitors. Among these compounds, compound 2-(3-(3,4-dimethylphenyl)-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl)thiazol-4(5H)-one (5a) displayed the most potent COX-2 inhibitory activity with IC50 of 0.5 mu M, but weak to COX-1. Docking simulation was performed to position compound 5a into the COX-2 active site to determine the probable binding model. Based on the preliminary results, compound 5a with potent inhibitory activity and low toxicity would be a potential and selective anti-cyclooxygenase-2 agent. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.09.021

文献信息

• Efficient Route to Highly Functionalized Chalcone-Based Pyranocoumarins via Iodine-Promoted Michael Addition Followed by Cyclization of 4-Hydroxycoumarins
  作者：Naseem Ahmed、B. Venkata Babu

  DOI：10.1080/00397911.2012.763099

  日期：2013.11.17

  Abstract Molecular iodine is used as an efficient promoter in the regioselective synthesis of highly functionalized chalcone-based pyranocoumarin derivatives using 4-hydroxycoumarin in acetic acid solvent at 100 °C. Under optimized reaction conditions, our protocol (Michael addition followed by intermolecular cyclization) has tolerance for many functional groups and gave products in good to excellent

  摘要 在 100 °C 的乙酸溶剂中使用 4-羟基香豆素对高度官能化的查尔酮基吡喃香豆素衍生物进行区域选择性合成时，分子碘被用作有效的促进剂。在优化的反应条件下，我们的方案（迈克尔加成，然后分子间环化）对许多官能团具有耐受性，并在 1-2 小时内以良好的产率（75-98%）提供产品。[本文提供补充材料。访问出版商的 Synthetic Communications® 在线版，获取以下免费补充资源：完整的实验和光谱细节。] 图形摘要
• Efficient green synthesis of antioxidant azacoumarin dye bearing spiro-pyrrolidine for enhancing electro-optical properties of perovskite solar cells
  作者：S.K. Attia、A.T. Elgendy、S.A. Rizk

  DOI：10.1016/j.molstruc.2019.02.042

  日期：2019.5

  reason, we focus in our work on enhancing the quality of perovskite materials in order to increase its efficiency towards light absorption and increase its photovoltaic behavior. Herein, different azacoumarin additives were prepared using a series of Spiro-indolone moieties and their structures were confirmed using Fourier transform infrared (FT-IR) spectroscopy and proton nuclear magnetic resonance (1H-NMR)

  摘要 提高太阳能电池产量在我们生活中面临的质量、效率和环境（环保）方面的挑战需要太阳能电池研究的不断改进。太阳能电池已成为满足日益增长的能源需求的强大技术。该领域采用的成功态度之一是使用钙钛矿材料，它提供了一种廉价的方法，可广泛用于制造太阳能电池。出于这个原因，我们专注于提高钙钛矿材料的质量，以提高其光吸收效率并增加其光伏性能。在此处，使用一系列螺-吲哚酮部分制备了不同的氮杂香豆素添加剂，并使用傅里叶变换红外 (FT-IR) 光谱和质子核磁共振 (1H-NMR) 确认了它们的结构。对制备的化合物进行了量子化学计算，以研究分子轨道参数并研究它们的定量结构-活性和结构-性质关系。所得结果表明这些化合物在染料敏化太阳能电池领域具有广阔的应用前景。更有趣的是，这些化合物已被证明是有效的润滑油抗氧化剂。所有这些说法都得到了实验证据的证实。对制备的化合物进行了量子化学计算，以研究分子轨道参数并研究它们
• Ultrasonic and Grinding Aptitudes of One‐Pot Synthesis of 5‐(4‐Chlorophenyl)‐7‐(3,4‐Dimethyl Phenyl)‐2‐oxo‐2H‐Pyrano[2,3‐b]Pyridine Derivatives as Antibacterial Agents
  作者：Sameh A. Rizk、Maher A. El‐Hashash、Azza A. El‐Badawy

  DOI：10.1002/jhet.2797

  日期：2017.5

  A simple facile “one‐pot” synthesis of 5‐(4‐chlorophenyl)‐7‐(3,4‐dimethyl phenyl)‐2‐oxo‐2H‐pyrano[2,3‐b]pyridine derivatives via three‐component reaction of chalcone, ethyl‐2‐substituted acetate, and ammonium acetate under ultrasonic irradiation and grinding tools. The newly synthesized compounds were evaluated for their antibacterial activity against ATCC 25923, ATCC 10987, ATCC 274, and SM514. All

  通过三组分反应简单轻松地“一锅”合成5-（4-氯苯基）-7-（3,4-二甲基苯基）-2-氧代-2H-吡喃并[2,3-b]吡啶衍生物在超声辐射和研磨工具的作用下制备查尔酮，2-乙基取代的乙酸盐和乙酸铵。评价新合成的化合物对ATCC 25923，ATCC 10987，ATCC 274和SM514的抗菌活性。所有合成的化合物均已根据其元素分析和光谱数据进行了表征。
• Synthesis, molecular docking and evaluation of thiazolyl-pyrazoline derivatives as EGFR TK inhibitors and potential anticancer agents
  作者：Peng-Cheng Lv、Dong-Dong Li、Qing-Shan Li、Xiang Lu、Zhu-Ping Xiao、Hai-Liang Zhu

  DOI：10.1016/j.bmcl.2011.07.010

  日期：2011.9

  Fourty-two thiazolyl-pyrazoline derivatives were synthesized to screen for their EGFR kinase inhibitory activity. Compound 4-(4-chlorophenyl)-2-(3-(3,4-dimethylphenyl)-5-p-tolyl-4,5-dihydro-1H-pyrazol-1-yl) thiazole (11) displayed the most potent EGFR TK inhibitory activity with IC(50) of 0.06 mu M, which was comparable to the positive control. Molecular docking results indicated that compound 11 was nicely bound to the EGFR kinase. Compound 11 also showed significant antiproliferative activity against MCF-7 with IC(50) of 0.07 mu M, which would be a potential anticancer agent. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis and biological evaluation of pyrazole derivatives containing thiourea skeleton as anticancer agents
  作者：Peng-Cheng Lv、Huan-Qiu Li、Juan Sun、Yang Zhou、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2010.05.034

  日期：2010.7

  Two series of pyrazole derivatives designing for potential EGFR kinase inhibitors have been discovered. Some of them exhibited significant EGFR inhibitory activity. Compound 3-(3,4-dimethylphenyl)-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide (C5) displayed the most potent EGFR inhibitory activity with IC50 of 0.07 mu M, which was comparable to the positive control erlotinib. Docking simulation was performed to position compound C5 into the EGFR active site to determine the probable binding model. Antiproliferative assay results indicating that some of the pyrazole derivatives own high antiproliferative activity against MCF-7. Compound C5 showed significant antiproliferative activity against MCF-7 with IC50 of 0.08 mu M. Therefore, compound C5 with potent inhibitory activity in tumor growth inhibition would be a potential anticancer agent. (C) 2010 Elsevier Ltd. All rights reserved.