2-(2-[4-(trifluoromethyl)phenyl]ethenyl)benzenamine | 1194058-37-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-(2-[4-(trifluoromethyl)phenyl]ethenyl)benzenamine
• 英文别名: 2-(4-(trifluoromethyl)styryl)aniline
• CAS: 1194058-37-1
• 化学式: C₁₅H₁₂F₃N
• 分子量: 263.262
• InChiKey: DOYHCXAGBVHXQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.46
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  26.02
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2,6-二叔丁基苯醌 、 2-(2-[4-(trifluoromethyl)phenyl]ethenyl)benzenamine 在 三氟乙酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以89%的产率得到2,6-di-tert-butyl-4-(2-(4-(trifluoromethyl)phenyl)-1H-indol-1-yl)phenol
  参考文献：
  名称：

  利用亚氨基醌作为氮“N+”合成子的亲电性来构建 C-N 键

  摘要：

  报道了利用亚氨基醌的 N 中心亲电特性构建 C-N 键的新方法。通过邻乙烯基苯胺与苯醌缩合原位生成的亚氨基醌经过酸催化环化以优异的产率得到N-芳基吲哚。在类似的反应条件下，高烯丙基胺类似地反应得到N-芳基吡咯。此外，有机金属亲核试剂显示出添加到N-烷基亚氨基醌的氮原子上以提供胺产物。最后，亚氨基醌被证明是铜催化加氢胺化反应的亲电试剂。

  DOI：

  10.1021/acs.orglett.1c00867
• 作为产物：
  描述：

  1-[2-[4-(三氟甲基)苯基]乙炔基]-2-硝基苯 在 5% Au/Fe2O3 、 氢气 作用下， 以 甲苯 为溶剂， 60.0~120.0 ℃ 、2.0 MPa 条件下， 反应 2.0h， 以43%的产率得到2-[4-(trifluoromethyl)phenyl]-1H-indole
  参考文献：
  名称：

  One-Pot Synthesis of Indoles and Aniline Derivatives from Nitroarenes under Hydrogenation Condition with Supported Gold Nanoparticles

  摘要：

  One-pot sequences of hydrogenation/hydroamination to form Indoles from (2-nitroaryl)alkynes and hydrogenation/reductive amination to form aniline derivatives from nitroarenes and aldehydes were catalyzed by Au nanoparticles supported on Fe2O3. Nitro group selective hydrogenations and successive reactions were efficiently catalyzed under the conditions.

  DOI：

  10.1021/ol902061j

文献信息

• Development of Tetrachlorophthalimides as Liver X Receptor β (LXRβ)-Selective Agonists
  作者：Sayaka Nomura、Kaori Endo-Umeda、Makoto Makishima、Yuichi Hashimoto、Minoru Ishikawa

  DOI：10.1002/cmdc.201600305

  日期：2016.10.19

  lipogenesis in liver, and selective LXRβ activation improves RCT in mice. Therefore, LXRβ‐selective agonists are promising candidates to improve atherosclerosis without increasing plasma or hepatic TG levels. However, the ligand‐binding domains in the two LXR isoforms α/β share high sequence identity, and few LXR ligands show subtype selectivity. In this study we identified a tetrachlorophthalimide analogue

  肝X受体（LXR）激动剂是通过诱导ABCA1（ATP结合盒A1）基因表达来治疗动脉粥样硬化的候选药物，该基因表达有助于逆转胆固醇转运（RCT）并促进肝脏和肠道中胆固醇的排出。但是，LXR激动剂也会诱导参与脂肪形成的基因，例如SREBP-1c（固醇调节结合元件蛋白1c）和FAS（脂肪酸合酶），从而引起血浆和肝甘油三酯（TG）水平的不良增加。最近的研究表明，LXRα有助于肝脏中的脂肪生成，选择性LXRβ活化可改善小鼠的RCT。因此，LXRβ选择性激动剂有望在不增加血浆或肝TG水平的情况下改善动脉粥样硬化。但是，两个LXR同工型α/β中的配体结合结构域具有较高的序列同一性，几乎没有LXR配体显示出亚型选择性。在这项研究中，我们确定了四氯邻苯二甲酰亚胺类似物作为LXRβ选择性激动剂。结构发展导致（E）-4,5,6,7-四氯-2-（2-苯乙烯基苯基）异吲哚啉-1,3-二酮（24 a），这在报告基因测
• Styrylphenylphthalimides as Novel Transrepression-Selective Liver X Receptor (LXR) Modulators
  作者：Sayaka Nomura、Kaori Endo-Umeda、Atsushi Aoyama、Makoto Makishima、Yuichi Hashimoto、Minoru Ishikawa

  DOI：10.1021/acsmedchemlett.5b00170

  日期：2015.8.13

  Anti-inflammatory effects of liver X receptor (LXR) ligands are thought to be largely due to LXR-mediated transrepression, whereas side effects are caused by activation of LXR-responsive gene expression (transactivation). Therefore, selective LXR modulators that preferentially exhibit transrepression activity should exhibit anti-inflammatory properties with fewer side effects. Here, we synthesized a series of styrylphenylphthalirnide analogues and evaluated their structure activity relationships focusing on LXRs-transactivating-agonistic/antagonistic activities and transrepressional activity. Among the compounds examined, 171 showed potent LXR-transrepressional activity with high selectivity over transactivating activity and did not show characteristic side effects of LXR-transactivating agonists in cells. This representative compound, 171, was confirmed to have LXR-dependent transrepressional activity and to bind directly to LXR beta. Compound 171 should be useful not only as a chemical tool for studying the biological functions of LXRs transrepression but also as a candidate for a safer agent to treat inflammatory diseases.
• An Expanded EDA Complex Profile: Construction of Aza-arenes and Their Synthetic Application as Fluorescence Probes
  作者：Qun-Liang Zhang、Bing Sun、Guanchang Ji、Guizhen Zhang、Fang-Lin Zhang

  DOI：10.1021/acs.orglett.3c03720

  日期：2024.1.12