2-bromo-1-(4-fluorophenyl)-3-phenylpropan-1-one | 1621006-55-0

• 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: 2-bromo-1-(4-fluorophenyl)-3-phenylpropan-1-one
• CAS: 1621006-55-0
• 化学式: C₁₅H₁₂BrFO
• 分子量: 307.162
• InChiKey: KGYPFFADCJAKEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.01
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-bromo-1-(4-fluorophenyl)-3-phenylpropan-1-one 在 sodium tetrahydroborate 、 sodium acetate 、 对甲苯磺酸 作用下， 以 乙醇 、 甲苯 为溶剂， 生成 5-benzyl-4-(4-fluorophenyl)-N-(4-methoxybenzyl)thiazol-2-amine
  参考文献：
  名称：

  2,4,5-Trisubstituted thiazole derivatives: A novel and potent class of non-nucleoside inhibitors of wild type and mutant HIV-1 reverse transcriptase

  摘要：

  Novel 2,4,5-trisubstituted thiazole derivatives (TSTs) were designed and synthesized as HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs). Among the thirty-eight synthesized target compounds, thirty TSTs showed potent inhibition against HIV-1 replication in wild type HIV-1 at submicromolar concentrations (from 0.046 to 9.59 mu M). Compounds 21, 23 and 24 were also tested on seven NNRTI-resistant HIV-1 strains, and all exhibited inhibitory effects with fold changes in IC50 ranging from 2.6 to 111, which were better than those of nevirapine (15.6-fold-371-fold). Docking simulations of compound 24 revealed a reasonable mechanism for the binding mode, and three-dimensional quantitative structure activity relationship (3-DQSAR) studies on this novel series of TST further elucidated the structure-activity relationship (SAR). The results suggested the great potential of TSTs as a novel class of NNRTIs with antiviral efficacy and a good resistance profile. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.07.072
• 作为产物：
  描述：

  苯甲醛 在 aluminum (III) chloride 、 palladium on activated charcoal 、 氢气 、 溴 、 sodium hydroxide 作用下， 以 乙醇 、 氯仿 、 水 、 乙酸乙酯 为溶剂， 反应 6.17h， 生成 2-bromo-1-(4-fluorophenyl)-3-phenylpropan-1-one
  参考文献：
  名称：

  2,4,5-Trisubstituted thiazole derivatives: A novel and potent class of non-nucleoside inhibitors of wild type and mutant HIV-1 reverse transcriptase

  摘要：

  Novel 2,4,5-trisubstituted thiazole derivatives (TSTs) were designed and synthesized as HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs). Among the thirty-eight synthesized target compounds, thirty TSTs showed potent inhibition against HIV-1 replication in wild type HIV-1 at submicromolar concentrations (from 0.046 to 9.59 mu M). Compounds 21, 23 and 24 were also tested on seven NNRTI-resistant HIV-1 strains, and all exhibited inhibitory effects with fold changes in IC50 ranging from 2.6 to 111, which were better than those of nevirapine (15.6-fold-371-fold). Docking simulations of compound 24 revealed a reasonable mechanism for the binding mode, and three-dimensional quantitative structure activity relationship (3-DQSAR) studies on this novel series of TST further elucidated the structure-activity relationship (SAR). The results suggested the great potential of TSTs as a novel class of NNRTIs with antiviral efficacy and a good resistance profile. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.07.072

文献信息

• α,α-Alkylation-Halogenation and Dihalogenation of Sulfoxonium Ylides. A Direct Preparation of Geminal Difunctionalized Ketones
  作者：Rafael D. C. Gallo、Anees Ahmad、Gustavo Metzker、Antonio C. B. Burtoloso

  DOI：10.1002/chem.201704609

  日期：2017.12.1

  A one‐pot alkylation–halogenation of ketosulfoxonium ylides in the presence of alkyl halides is described. The method furnishes several gem‐difunctionalized haloketones (an alkyl and F, Cl, Br, or I) in good yields. Replacing alkyl halides with a mixture of electrophilic halogen species and various halide anions led to gem‐dihalogenated ketones containing a combination of the same or two different

  描述了在存在烷基卤化物的情况下一酮醚化ox酮的一锅烷基化-卤化反应。该方法以良好的收率提供了几种宝石双官能化的卤代酮（烷基和F，Cl，Br或I）。用亲电子卤素物质和各种卤化物阴离子的混合物代替烷基卤化物，会导致宝石二卤代酮含有相同或两种不同卤素的组合。动力学同位素效应以及反应动力学实验使人们洞悉了这些反应的机理。