1-(4-bromophenyl)-3-(4-fluorophenyl)prop-2-en-1-one | 98991-32-3

• 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: 1-(4-bromophenyl)-3-(4-fluorophenyl)prop-2-en-1-one
• 英文别名: 3-(4-fluorophenyl)-1-(4-bromophenyl)-2-propen-1-one；2-Propen-1-one, 1-(4-bromophenyl)-3-(4-fluorophenyl)-
• CAS: 98991-32-3
• 化学式: C₁₅H₁₀BrFO
• mdl: MFCD00446111
• 分子量: 305.146
• InChiKey: JLKQXQSMJJGERH-UHFFFAOYSA-N

物化性质

• 熔点：
  133～135℃
• 沸点：
  400.6±45.0 °C(Predicted)
• 密度：
  1.451±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 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：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-bromophenyl)-3-(4-fluorophenyl)prop-2-en-1-one 在 盐酸羟胺 作用下， 以 吡啶 为溶剂， 以63%的产率得到1-(4-bromophenyl)-3-(4-fluorophenyl)prop-2-en-1-one oxime
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of chalcone oxime derivatives as potential immunosuppressive agents

  摘要：

  A series of deoxybenzoin oximes were recently reported as potent immunosuppressive agents by our group. In order to continue the original research for potential immunosuppressive agents with high efficacy and low toxicity, we synthesized a series of new chalcone oximes and evaluated them for their cytotoxicities and immunosuppressive activities. Among the synthesized compounds, chalcone oximes 25 and 27 exhibited lower cytotoxicities and higher inhibitory activities on anti-CD3/anti-CD28 co-stimulated lymph node cells than other compounds. Specially, compound 27 displayed 200-fold lower cytotoxicity (CC50 = 2174.39 mu M) than cyclosporin A (CC50 = 10.10 mu M) and showed SI value (SI = 176.69) close to cyclosporin A (SI = 154.13). Besides, the preliminary mechanism of inhibition effect of compounds 25 and 27 was also detected by flow cytometry, and the compounds exerted immunosuppressive activities via inducing the apoptosis of activated lymph node cells in a dose dependent manner. Also, the deep mechanism of apoptosis was detected by Western blot analysis. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.080
• 作为产物：
  描述：

  对氟苯甲醛 、 4-溴苯乙酮 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.08h， 生成 1-(4-bromophenyl)-3-(4-fluorophenyl)prop-2-en-1-one
  参考文献：
  名称：

  手性有机催化剂催化高效无碱不对称一锅合成螺[吲哚啉-3,3'-吡咯嗪] -2-one衍生物

  摘要：

  通过使用基于联吡啶的手性季铵溴化铵作为有机催化剂，在高对映选择性的有机催化条件下进行了1,3-偶极环加成反应。这里，生成的偶氮甲碱内鎓盐的1,3-偶极环加成的反应在原位从的脱羧缩合α -氨基酸和非烯醇化的1,2-二酮上述dipolarophiles发生。

  DOI：

  10.1007/s11164-020-04303-8

文献信息

• Primary-Secondary Diamine Catalyzed Enantioselective Synthesis of Substituted Cyclohex-2-enones by Cascade Michael–Aldol–­Dehydration of Ketones with Chalcones
  作者：Sandip Wagh、Ganesh Dhage

  DOI：10.1055/s-0036-1588976

  日期：2017.7

  A simple primary-secondary diamine organocatalyst catalyzes the cascade Michael–aldol–dehydration of chalcones and unmodified ketones to produce substituted cyclohex-2-enones under mild conditions with good yields and high enantio- and/or diastereoselectivities. The success of the catalyst system is possibly due to simultaneous activation of the electrophilic chalcone by iminium formation and the nu­cleophilic

  一种简单的伯仲二胺有机催化剂催化查耳酮和未改性酮的级联迈克尔-羟醛脱水，在温和条件下以良好的收率和高对映选择性和/或非对映选择性生产取代的环己-2-烯酮。催化剂体系的成功可能是由于通过亚胺形成同时激活亲电子查耳酮和通过烯胺形成同时活化亲核酮，具有整体分子内亚胺-二烯胺机制。
• Novel benzothiazole based sulfonylureas/sulfonylthioureas: design, synthesis and evaluation of their antidiabetic potential
  作者：Chetna Kharbanda、Mohammad Sarwar Alam、Hinna Hamid、Kalim Javed、Sameena Bano、Yakub Ali、Abhijeet Dhulap、Parwez Alam、M. A. Q. Pasha

  DOI：10.1039/c5nj03589a

  日期：——

  Twenty-eight benzothiazole based sulfonylureas/sulfonylthioureas were synthesized and were found to be effective against diabetes as PPAR-γ agonists.

  合成了 28 种基于苯并噻唑的磺酰脲类/磺酰硫脲类，发现它们作为 PPAR-γ 激动剂对糖尿病有效。
• Synthesis, spectral investigation and biological interphase of drug-based cytotoxic square pyramidal coordination compounds
  作者：Mohan N. Patel、Bhupesh S. Bhatt、Promise A. Dosi、Narasimhacharya V. R. L. Amaravady、Hetal V. Movaliya

  DOI：10.1002/aoc.2841

  日期：2012.5

  in terms of minimum inhibitory concentration. Superoxide dismutase mimic studies were performed using the NADH/PMS/NBT system. The brine shrimp bioassay was also carried out to study the in vitro cytotoxic properties of the synthesized metal complexes. Copyright © 2012 John Wiley & Sons, Ltd.

  我们已经合成了联吡啶衍生物[Cu（CFL）（A n）Cl] .2H 2 O（其中CFL =环丙沙星和A =联吡啶，例如A 1  = 4-（4-氟苯基）-6- p）基于环丙沙星的金属配合物-tolyl-2,2'-联吡啶，A 6  = 4-（4-（苄氧基）苯基）-6-（4-溴苯基）-2,2'-联吡啶等）。配体和配合物的特征在于分析（C，H，N元素分析，TGA和磁测量）和光谱法（1 H和13C NMR，FT-IR，快速原子轰击质量和反射光谱）。通过筛选鲱鱼精DNA上的DNA相互作用活性来评估产品，研究表明DNA结合的插入模式。根据最小抑制浓度确定抗微生物活性。超氧化物歧化酶模拟研究是使用NADH / PMS / NBT系统进行的。还进行了盐水虾生物测定，以研究合成金属配合物的体外细胞毒性。版权所有©2012 John Wiley＆Sons，Ltd.
• Synthesis and evaluation of pyrazolines bearing benzothiazole as anti-inflammatory agents
  作者：Chetna Kharbanda、Mohammad Sarwar Alam、Hinna Hamid、Kalim Javed、Sameena Bano、Abhijeet Dhulap、Yakub Ali、Syed Nazreen、Saqlain Haider

  DOI：10.1016/j.bmc.2014.09.028

  日期：2014.11

  aims at the synthesis of pyrazolines bearing benzothiazole and their evaluation as anti-inflammatory agents. The synthesized compounds were evaluated for their anti-inflammatory potential using carrageenan induced paw edema model. Two compounds 5a and 5d alleviated inflammation more than the standard drug celecoxib. Eight compounds 5b, 5c, 5e, 5g, 5h, 6b, 6e and 6f showed anti-inflammatory activity comparable

  本研究旨在合成带有苯并噻唑的吡唑啉及其作为抗炎药的评价。使用角叉菜胶诱导的爪水肿模型评价合成的化合物的抗炎潜力。两种化合物5a和5d比标准药物塞来昔布更能减轻炎症。八个化合物5b，5c，5e，5g，5h，6b，6e和6f显示出与塞来昔布相当的抗炎活性。为了理解作用方式，进行了COX-2酶测定和TNF-α测定。评估所有活性化合物的细胞毒性。对未发现有细胞毒性的活性化合物进行了致溃疡风险评估。在十种活性化合物中，最终发现两种化合物（5d和6f）是最有效的抗炎药，可抑制COX-2酶活性和TNF-α的产生，而不会产生细胞毒性或致溃疡性。
• Transition metal-free domino aryl-aryl coupling/phospha-Michael addition of diarylphosphinite to α,β-unsaturated ketones triggered by alkaline hydrolysis of (4-(2-alkenoyl)phenyl)triarylphosphonium salts
  作者：Wenhua Huang、Jing-Yu Xue

  DOI：10.1080/10426507.2021.1995385

  日期：2022.2.1

  Abstract Alkaline hydrolysis of a variety of (4-(2-alkenoyl)phenyl)triarylphosphonium bromides is reported. This hydrolysis triggers coupling of 4-(2-alkenoyl)phenyl with one aryl via phosphorus(V). Both diarylphosphinite and an α,β-unsaturated ketone are in situ generated and then undergo phospha-Michael addition to provide β-diarylphosphoryl ketones bearing a biaryl moiety in 27–70% yields in the

  摘要 报道了多种(4-(2-烯酰基)苯基)三芳基溴化鏻的碱性水解。这种水解触发 4-(2-烯酰基) 苯基与一个芳基通过磷 (V) 偶联。二芳基亚膦酸酯和 α,β-不饱和酮都是原位生成的，然后在没有过渡金属的情况下以 27-70% 的产率提供带有联芳基部分的 β-二芳基磷酰基酮，然后进行 phospha-Michael 加成。