3-((4-methoxyphenyl)ethynyl)aniline | 1182977-32-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-((4-methoxyphenyl)ethynyl)aniline
• 英文别名: 1-methoxy-4-(3-aminophenylethynyl)benzene；3-(4-Methoxy-phenylethynyl)-phenylamine；3-[2-(4-methoxyphenyl)ethynyl]aniline
• CAS: 1182977-32-7
• 化学式: C₁₅H₁₃NO
• 分子量: 223.274
• InChiKey: VCTOWTCEALJPRO-UHFFFAOYSA-N

物化性质

• 沸点：
  412.0±30.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-((4-methoxyphenyl)ethynyl)aniline 、 4-aminobenzamidine dihydrochloride 在 盐酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 0.5h， 以31%的产率得到(E)-4-(3-(3-((4-methoxyphenyl)ethynyl)phenyl)triaz-1-enyl)benzimidamide
  参考文献：
  名称：

  Alkyne-substituted diminazene as G-quadruplex binders with anticancer activities

  摘要：

  G-quadruplex ligands have been touted as potential anticancer agents, however, none of the reported G-quadruplex-interactive small molecules have gone past phase II clinical trials. Recently it was revealed that diminazene (berenil, DMZ) actually binds to G-quadruplexes 1000 times better than DNA duplexes, with dissociation constants approaching 1 nM. DMZ however does not have strong anticancer activities. In this paper, using a panel of biophysical tools, including NMR, FRET melting assay and FRET competition assay, we discovered that monoamidine analogues of DMZ bearing alkyne substitutes selectively bind to G-quadruplexes. The lead DMZ analogues were shown to be able to target c-MYC G-quadruplex both in vitro and in vivo. Alkyne DMZ analogues display respectable anticancer activities (single digit micromolar GI(50)) against ovarian (OVCAR-3), prostate (PC-3) and triple negative breast (MDA-MB-231) cancer cell lines and represent interesting new leads to develop anticancer agents. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.04.030
• 作为产物：
  描述：

  4-碘苯甲醚 、 3-氨基苯乙炔 在 tris-(dibenzylideneacetone)dipalladium(0) 、 potassium phosphate tribasic heptahydrate 作用下， 以 乙醇 、 水 为溶剂， 反应 1.5h， 以95%的产率得到3-((4-methoxyphenyl)ethynyl)aniline
  参考文献：
  名称：

  在水性介质中钯催化的膦、无铜和有氧 Sonogashira 偶联

  摘要：

  在水性、无铜和有氧条件下，使用 Pd2(dba)3（dba=二亚苄基丙酮）作为催化剂，开发了一种简单、高效且不含膦的方案，用于芳基碘化物与末端炔烃的 Sonogashira 偶联。芳基碘化物与芳族末端炔烃的偶联提供了良好到极好的产率，并且使用脂族末端炔烃作为偶联伙伴之一实现了中等至良好的产率。根据绿色化学的概念，乙醇水溶液作为溶剂经济且环保。

  DOI：

  10.3998/ark.5550190.0012.b06

文献信息

• Synthesis and characterization of recyclable and recoverable MMT-clay exchanged ammonium tagged carbapalladacycle catalyst for Mizoroki–Heck and Sonogashira reactions in ionic liquid media
  作者：Vasundhara Singh、Rajni Ratti、Sukhbir Kaur

  DOI：10.1016/j.molcata.2010.10.015

  日期：2011.1

  carbapalladacycle 5 assists in the pillaring process and enhances the organophilicity of catalyst 6 in the interlayers of clay. The catalytic activity in ammonium based ionic liquid [TMBA] NTf2 of both the homogeneous and heterogeneous recyclable catalysts 5 and 6 respectively in micromolar concentration of palladium has been tested for Mizoroki–Heck and Sonogashira reactions in good yields with high TON/TOF and

  已经实现了以适度的产率高效合成铵标记的咔哒哒哒啉5。此外，通过将5离子交换成粘土夹层作为新的有机-无机杂化催化体系，可以制备粘土-纳米复合材料6。铵负载的咔唑四环素5的离子标签有助于柱化过程，并增强了粘土中间层中催化剂6的亲有机性。均相和非均相可循环催化剂5和6在铵基离子液体[TMBA] NTf 2中的催化活性已经测试了分别以微摩尔浓度的钯进行Mizoroki-Heck和Sonogashira反应的高产率，高TON / TOF和可忽略不计的金属浸出。还研究了溶剂和温度对催化活性的影响。
• Functionalized α,β-ynones: efficient ligand for Cu catalyzed Sonogashira-type cross-coupling reaction
  作者：Xian Wang、Zhenhua Wang、Zunyuan Xie、Guofang Zhang、Weiqiang Zhang、Ziwei Gao

  DOI：10.1039/c6ra23742h

  日期：——

  donor ligands were mandatory for the catalytic cross-coupling of Csp2–Csp bonds. Herein, we wish to report α,β-ynones as σ-, π-electron donating ligands for copper catalyzed Sonogashira-type reaction. As low as 0.25–2.5 mol% of L11 (3-(4-bromophenyl)-1-(4-methoxyphenyl)prop-2-yn-1-one) significantly accelerated the 0.1–1.0 mol% of CuI catalyzed cross-coupling of aryl iodides with terminal alkynes and

  在经典的反应条件下，大量的铜催化剂和N，O供体配体对于Csp 2 -Csp键的催化交叉偶联是必需的。在此，我们希望报道α，β-炔酮作为铜催化的Sonogashira型反应的σ-，π-电子给体。低至0.25–2.5 mol％的L 11（3-（4-溴苯基）-1-（4-甲氧基苯基）prop-2-yn-1-one）显着加速了0.1–1.0 mol％的CuI催化的交叉芳基碘化物分别与末端炔烃和炔基羧酸偶联。这种低摩尔％的催化剂体系具有36个取代炔烃实例，显示出令人满意的活性和耐受性。
• Cu/Oxalic Diamide-Catalyzed Coupling of Terminal Alkynes with Aryl Halides
  作者：Ying Chen、Sailuo Li、Lanting Xu、Dawei Ma

  DOI：10.1021/acs.joc.2c02882

  日期：2023.3.3

  6-Dimethylphenyl)-N2-(pyridin-2-ylmethyl)oxalamide (DMPPO) was revealed to be a more effective ligand for copper-catalyzed coupling reaction of (hetero)aryl halides with 1-alkynes than previously reported ones. Only 3 mol % CuCl and DMPPO are required to make the coupling complete at 100 °C (for bromides) and 80 °C (for iodides). Both (hetero)aryl and alkyl substituted 1-alkynes worked well under these conditions

  N 1 -(2,6-二甲基苯基)- N 2 -(吡啶-2-基甲基)草酰胺 (DMPPO) 被发现是铜催化的（杂）芳基卤化物与 1-炔烃偶联反应的更有效配体以前报道过的。仅需 3 mol% CuCl 和 DMPPO 即可在 100 °C（溴化物）和 80 °C（碘化物）下完成偶联。（杂）芳基和烷基取代的 1-炔烃在这些条件下都表现良好，导致内部炔烃的形成具有很大的多样性。
• LINKED DIARYL COMPOUNDS WITH ANTICANCER PROPERTIES AND METHODS OF USING THE SAME
  申请人：University of Maryland, College Park

  公开号：US20170174620A1

  公开（公告）日：2017-06-22

  Provided are compositions comprising linked diaryl compounds that possess anticancer properties. Methods of use are also disclosed herein. The method comprises administering an effective amount of a compound described herein to an individual in need thereof.
• [EN] LINKED DIARYL COMPOUNDS WITH ANTICANCER PROPERTIES AND METHODS OF USING THE SAME<br/>[FR] COMPOSÉS BIARYLES LIÉS À PROPRIÉTÉS ANTICANCÉREUSES ET LEURS PROCÉDÉS D'UTILISATION
  申请人：UNIV MARYLAND

  公开号：WO2016014674A1

  公开（公告）日：2016-01-28

  Provided are compositions comprising linked diaryl compounds that possess anticancer properties. Methods of use are also disclosed herein. The method comprises administering an effective amount of a compound described herein to an individual in need thereof.