2-溴-3-(4-氯苯基)-1-苯基丙烷-1-酮 | 113478-79-8

• 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
• 中文名称: 2-溴-3-(4-氯苯基)-1-苯基丙烷-1-酮
• 英文名称: 2-bromo-3-(4-chlorophenyl)-1-phenylpropane-1-one
• 英文别名: 2-Bromo-3-(4-chlorophenyl)-1-phenylpropan-1-one
• CAS: 113478-79-8
• 化学式: C₁₅H₁₂BrClO
• 分子量: 323.617
• InChiKey: XZPFUVGWBBBMCB-UHFFFAOYSA-N

物化性质

• 熔点：
  82 °C
• 沸点：
  403.6±35.0 °C(Predicted)
• 密度：
  1.446±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  2-溴-3-(4-氯苯基)-1-苯基丙烷-1-酮 在 sodium acetate 、 对甲苯磺酸 作用下， 以 乙醇 、 甲苯 为溶剂， 生成
  参考文献：
  名称：

  2,4,5-Trisubstituted thiazole derivatives as HIV-1 NNRTIs effective on both wild-type and mutant HIV-1 reverse transcriptase: Optimization of the substitution of positions 4 and 5

  摘要：

  In our previous work, novel 2,4,5-trisubstituted thiazole derivatives (TSTs) were synthesized, and their activities were evaluated against HIV-1 reverse transcriptase. Some interesting results were obtained, which led us to a new discovery regarding these TST5. In the present study, 21 new 2,4,5-trisubstituted thiazole derivatives were rationally designed and synthesized as HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs) in accordance with our previous study. Among the synthesized target compounds, compounds 14, 16, 17, and 19 showed more potent inhibitory activities against HIV-1 with an IC50 value of 0.010 mu M. Compounds 4, 9, 10, 11, 13 and 16 were further tested on nine NNRTI-sresistant HIV-1 strains, and all of these compounds exhibited inhibitory effects. A molecular docking study was conducted, and the results showed a consistent and stable binding mode for the typical compounds. These results have provided deeper insights and SAR of these types of NNRTIs. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.07.047
• 作为产物：
  描述：

  4-氯苯甲醛 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 0.17h， 生成 2-溴-3-(4-氯苯基)-1-苯基丙烷-1-酮
  参考文献：
  名称：

  2,4,5-Trisubstituted thiazole derivatives as HIV-1 NNRTIs effective on both wild-type and mutant HIV-1 reverse transcriptase: Optimization of the substitution of positions 4 and 5

  摘要：

  In our previous work, novel 2,4,5-trisubstituted thiazole derivatives (TSTs) were synthesized, and their activities were evaluated against HIV-1 reverse transcriptase. Some interesting results were obtained, which led us to a new discovery regarding these TST5. In the present study, 21 new 2,4,5-trisubstituted thiazole derivatives were rationally designed and synthesized as HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs) in accordance with our previous study. Among the synthesized target compounds, compounds 14, 16, 17, and 19 showed more potent inhibitory activities against HIV-1 with an IC50 value of 0.010 mu M. Compounds 4, 9, 10, 11, 13 and 16 were further tested on nine NNRTI-sresistant HIV-1 strains, and all of these compounds exhibited inhibitory effects. A molecular docking study was conducted, and the results showed a consistent and stable binding mode for the typical compounds. These results have provided deeper insights and SAR of these types of NNRTIs. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.07.047

文献信息

• Silica Sulfuric Acid-promoted Deacylation of α-Bromo-β-diketones
  作者：Tadashi Aoyama、Sho Kubota、Toshio Takido、Mitsuo Kodomari

  DOI：10.1246/cl.2011.484

  日期：2011.5.5

  Novel deacylation of α-bromo-β-diketones using silica sulfuric acid (SSA) has been developed. Deacylation of 3-bromopentane-2,4-diones and 2-bromobutane-1,3-diones were carried out in the presence of SSA in dichloroethane under mild conditions to obtain the corresponding α-bromo ketones in good to excellent yields. SSA also promoted the Friedel–Crafts type alkylation of benzene with 3-(sec-alkyl)-2,4-pentanediones to give the corresponding triarylmethanes in high yields in benzene.

  利用二氧化硅硫酸（SSA）开发出了α-溴-β-二酮的新型脱乙酰化方法。在 SSA 存在下，在温和条件下，在二氯乙烷中对 3-溴戊烷-2,4-二酮和 2-溴丁烷-1,3-二酮进行了脱乙酰化反应，得到了相应的α-溴酮，收率从良好到极佳。SSA 还能促进苯与 3-(仲烷基)-2,4-戊二酮的 Friedel-Crafts 型烷基化反应，从而在苯中高产率地得到相应的三芳基甲烷。
• Simple Method for sp2–sp3 and sp3–sp3 Carbon–Carbon Bond Activation in 2-Substituted 1,3-Diketones
  作者：Tadashi Aoyama、Mamiko Hayakawa、Sho Kubota、Sumire Ogawa、Erika Nakajima、Emi Mitsuyama、Taku Iwabuchi、Haruki Kaneko、Rina Obara、Toshio Takido、Mitsuo Kodomari、Akihiko Ouchi

  DOI：10.1055/s-0034-1378862

  日期：——

  Simple and efficient methods were developed for sp(2)-sp(3) and sp(3)-sp(3) C-C bond-activation reactions of 2-substituted 1,3-diketones. 3-Substituted 3-bromopentane-2,4-diones were deacylated in the presence of an aromatic compound and a silica gel supported Bronsted acid containing sulfonic groups. The carbocation formed by cleavage of the sp(3)-sp(3) C-C bond of the dione alkylated the aromatic compound.
• 3-Aryl-2-benzyl -1,2-dihydroquinoxalines
  作者：V. D. Orlov、B. Insuasti、N. N. Kolos

  DOI：10.1007/bf00486920

  日期：1987.6
• ORLOV, V. D.;INSUASTI, B.;KOLOS, N. N., XIMIYA GETEROTSIKL. SOED.,(1987) N 6, 830-832
  作者：ORLOV, V. D.、INSUASTI, B.、KOLOS, N. N.

  DOI：——

  日期：——
• 2,4,5-Trisubstituted thiazole derivatives as HIV-1 NNRTIs effective on both wild-type and mutant HIV-1 reverse transcriptase: Optimization of the substitution of positions 4 and 5
  作者：Zhongliang Xu、Jiamei Guo、Ying Yang、Mengdi Zhang、Mingyu Ba、Zhenzhong Li、Yingli Cao、Ricai He、Miao Yu、Hua Zhou、Xiaoxi Li、Xiaoshan Huang、Ying Guo、Changbin Guo

  DOI：10.1016/j.ejmech.2016.07.047

  日期：2016.11

  In our previous work, novel 2,4,5-trisubstituted thiazole derivatives (TSTs) were synthesized, and their activities were evaluated against HIV-1 reverse transcriptase. Some interesting results were obtained, which led us to a new discovery regarding these TST5. In the present study, 21 new 2,4,5-trisubstituted thiazole derivatives were rationally designed and synthesized as HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs) in accordance with our previous study. Among the synthesized target compounds, compounds 14, 16, 17, and 19 showed more potent inhibitory activities against HIV-1 with an IC50 value of 0.010 mu M. Compounds 4, 9, 10, 11, 13 and 16 were further tested on nine NNRTI-sresistant HIV-1 strains, and all of these compounds exhibited inhibitory effects. A molecular docking study was conducted, and the results showed a consistent and stable binding mode for the typical compounds. These results have provided deeper insights and SAR of these types of NNRTIs. (C) 2016 Elsevier Masson SAS. All rights reserved.