1-(4-methoxyphenyl)-3-(4-nitrophenyl)propan-1-one | 35031-93-7

• 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-methoxyphenyl)-3-(4-nitrophenyl)propan-1-one
• 英文别名: 1-(4-Methoxy-phenyl)-3-(4-nitro-phenyl)-propan-1-one
• CAS: 35031-93-7
• 化学式: C₁₆H₁₅NO₄
• 分子量: 285.299
• InChiKey: FFHWRWWQXRSSGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4-methoxyphenyl)-3-(4-nitrophenyl)propan-1-one 在 aluminum (III) chloride 、 溴 、 sodium acetate 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 6.0h， 生成 4-(4-methoxyphenyl)-5-(4-nitrobenzyl)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：

  3-(4-硝基苯基)丙酸 在 aluminum (III) chloride 、 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 生成 1-(4-methoxyphenyl)-3-(4-nitrophenyl)propan-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

• 一种新型芳香酮类化合物的制备方法
  申请人：河南师范大学

  公开号：CN111978168B

  公开（公告）日：2022-09-09

  本发明公开了一种新型芳香酮类化合物的制备方法，以芳香羧酸类化合物和芳香烯烃类化合物为反应原料，以三苯基膦作为脱氧试剂，以Methylene blue作为光催化剂，在白光灯照射下同时在氮气氛围和用2,4,6‑三甲基吡啶作碱的条件下，在N,N‑二甲基乙酰胺溶剂中于室温搅拌反应制得目标产物芳香酮类化合物。本发明具有反应条件温和、操作简单、成本低廉、便于纯化及环境友好等优点。
• Iron-catalyzed chemoselective hydride transfer reactions
  作者：Sébastien Coufourier、Daouda Ndiaye、Quentin Gaignard Gaillard、Léo Bettoni、Nicolas Joly、Mbaye Diagne Mbaye、Albert Poater、Sylvain Gaillard、Jean-Luc Renaud

  DOI：10.1016/j.tet.2021.132187

  日期：2021.6

  A Diaminocyclopentadienone iron tricarbonyl complex has been applied in chemoselective hydrogen transfer reductions. This bifunctional iron complex demonstrated a broad applicability in mild conditions in various reactions, such as reduction of aldehydes over ketones, reductive alkylation of various functionalized amines with functionalized aldehydes and reduction of α,β-unsaturated ketones into the

  二氨基环戊二烯酮三羰基铁络合物已用于减少化学选择性的氢转移。该双官能铁络合物在温和条件下的各种反应中显示出广泛的适用性，例如醛在酮上的还原，各种官能化胺与官能化醛的还原烷基化以及α，β-不饱和酮还原为相应的饱和酮。通过这种实用的方法，已经以优异的产率分离了多种功能化的底物。
• Ligated Regioselective PdII Catalysis to Access β-Aryl-Bearing Aldehydes, Ketones, and β-Keto Esters
  作者：Mari Vellakkaran、Murugaiah M. S. Andappan、Nagaiah Kommu

  DOI：10.1002/ejoc.201200770

  日期：2012.9

  arylative isomerization of allyl alcohols, a milder and regioselective access to the versatile building blocks β-aryl aldehydes and ketones was developed. This new and chelation-controlled protocol enabled the compatibility of wide range of functionalities to generate dihydrochalcones, α-benzyl-α′-alkyl acetones, dihydrocinnamaldehydes, and α-benzyl β-keto esters (from Baylis–Hillman adducts). A practical

  通过在 PdII 介导的烯丙醇芳基化异构化中使用配体，开发了一种更温和和区域选择性的通用构建块 β-芳基醛和酮。这种新的螯合控制方案使广泛的功能兼容，以生成二氢查耳酮、α-苄基-α'-烷基丙酮、二氢肉桂醛和 α-苄基 β-酮酯（来自 Baylis-Hillman 加合物）。还展示了普罗帕酮中间体的实用多克合成。
• Utility of Organoboron Reagents in Arylation of Cyclopropanols via Chelated Pd(II) Catalysis: Chemoselective Access to β-Aryl Ketones
  作者：Thangeswaran Ramar、Murugaiah A. M. Subbaiah、Andivelu Ilangovan

  DOI：10.1021/acs.joc.0c00160

  日期：2020.6.19

  Organoborane reagents were investigated as coupling partners to cyclopropanol-derived β-ketone enolates in the presence of a chelated Pd(II) catalyst. Efficient coupling of a range of electronically and sterically diverse cyclopropanols and aryl/alkenyl boronic derivatives (39 examples, 65–94% yield) could be achieved with the generation of synthetically important β-aryl ketone intermediates in a chemoselective

  在螯合的Pd（II）催化剂存在下，研究了有机硼烷试剂作为与环丙醇衍生的β-酮烯酸酯的偶联伙伴。通过化学选择性的方式生成具有重要合成意义的重要的β-芳基酮中间体，可以实现多种电子和空间上不同的环丙醇与芳基/烯基硼酸酯衍生物的高效偶联（39个实例，收率65-94％）。这种反应范式将芳基供体伙伴的范围扩大至均烯酸酯，允许开瓶条件，以水为助溶剂并制备与以往方法不同的含卤素β-芳基酮。这种螯合的Pd（II）催化作用似乎不同于Pd（0）途径，
• TRISUBSTITUTED THIAZOLE COMPOUNDS, PREPARATIONS METHODS, PHARMACEUTICAL COMPOSITIONS AND MEDICALS USES THEREOF
  申请人：Li Song

  公开号：US20090298832A1

  公开（公告）日：2009-12-03

  The present invention relates to 2,4,5-trisubstituted thiazole compounds of formula (I) or all possible isomers, prodrugs, pharmaceutically acceptable salts, solvates or hydrates thereof for the inhibition of plasma PLTP activity and/or plasma CETP activity, wherein the substituents are as defined in the specification; a process for the preparation of the compounds of formula (I); a pharmaceutical composition comprising the compound of formula (I) and its use for the preparation of a medicament for treatment and/or prevention of diseases associated with the increased plasma PLTP activity and/or the increased plasma CETP activity in a mammal, such as atherosclerosis, cardiovascular diseases and peripheral vascular diseases, etc.

  本发明涉及公式（I）的2,4,5-三取代噻唑化合物或所有可能的异构体、前药、药用盐、溶剂合物或水合物，用于抑制血浆PLTP活性和/或血浆CETP活性，其中取代基如规范中定义；一种用于制备公式（I）化合物的方法；包括公式（I）化合物的药物组合物以及其用于制备治疗和/或预防与哺乳动物体内增加的血浆PLTP活性和/或增加的血浆CETP活性相关的疾病的药物的用途，如动脉粥样硬化、心血管疾病和周围血管疾病等。