(E)-1-(2-chlorophenyl)-3-(2-methoxyphenyl)prop-2-en-1-one | 1032917-58-0

• 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: (E)-1-(2-chlorophenyl)-3-(2-methoxyphenyl)prop-2-en-1-one
• 英文别名: (2E)-1-(2-Chlorophenyl)-3-(2-methoxyphenyl)prop-2-en-1-one
• CAS: 1032917-58-0
• 化学式: C₁₆H₁₃ClO₂
• 分子量: 272.731
• InChiKey: JGUQGCUHFZPJIU-ZHACJKMWSA-N

物化性质

• 沸点：
  421.2±45.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-1-(2-chlorophenyl)-3-(2-methoxyphenyl)prop-2-en-1-one 在 palladium on activated charcoal 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 以82.8%的产率得到1-(2-氯苯基)-3-(2-甲氧基苯基)-1-丙酮
  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
• 作为产物：
  描述：

  邻氯苯乙酮 、 邻甲氧基苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 0.17h， 以89.2%的产率得到(E)-1-(2-chlorophenyl)-3-(2-methoxyphenyl)prop-2-en-1-one
  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

• Chiral Phosphoric Acid Catalyzed Asymmetric Friedel–Crafts Alkylation of Indoles with Simple α,β-Unsaturated Aromatic Ketones
  作者：Hong-Ying Tang、Ai-Dang Lu、Zheng-Hong Zhou、Guo-Feng Zhao、Lian-Nian He、Chu-Chi Tang

  DOI：10.1002/ejoc.200700980

  日期：2008.3

  Asymmetric Michael-type Friedel–Crafts (F-C) alkylations of indoles with nonchelating α,β-unsaturated aromatic ketones catalyzed by a chiral H8-BINOL-based phosphoric acid were investigated. The reactions took place smoothly in the presence of only 2 mol-% of catalyst at room temperature to afford the desired F-C alkylation products in good yields and with moderate enantioselectivities.(© Wiley-VCH

  研究了由基于手性 H8-BINOL 的磷酸催化的吲哚与非螯合 α,β-不饱和芳族酮的不对称迈克尔型 Friedel-Crafts (FC) 烷基化反应。反应在室温下仅 2 mol% 的催化剂存在下顺利进行，以良好的收率和适度的对映选择性提供所需的 FC 烷基化产物。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany , 2008)
• 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.