4,4'-(phenylmethylene)bis(1,3-dimethoxybenzene) | 53786-85-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 4,4'-(phenylmethylene)bis(1,3-dimethoxybenzene)
• 英文别名: 1-[(2,4-Dimethoxyphenyl)-phenylmethyl]-2,4-dimethoxybenzene；1-[(2,4-dimethoxyphenyl)-phenylmethyl]-2,4-dimethoxybenzene
• CAS: 53786-85-9
• 化学式: C₂₃H₂₄O₄
• 分子量: 364.441
• InChiKey: ZLCNKBMRKJUVIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,4-dimethoxybenzophenone 在 乙醇 、 硫酸 、 镍 作用下， 生成 4,4'-(phenylmethylene)bis(1,3-dimethoxybenzene)
  参考文献：
  名称：

  Davies et al., Journal of the Chemical Society, 1957, p. 3154,3156

  摘要：

  DOI：

文献信息

• Green Synthesis and Antiviral Activity of Novel Triarylmethane Derivatives via Friedel-Crafts Alkylation by Polyethylene Glycol (PEG-400)
  作者：N. Revaprasadu、C. Sampath、P. Harika

  DOI：10.14233/ajchem.2016.19122

  日期：——

  A series of novel triarylmethane derivatives (3a-j) were synthesized by a one-pot, two-component method via Friedel-Crafts alkylation of various electron-rich arenes (1a-j) with a wide variety of aldehydes (2a-j) in presence of the polyethylene glycol (PEG-400) as a green solvent at 50-60 °C in good to excellent yields (76-96 %). Their structures were confirmed by FT-IR, 1H NMR, 13C NMR, mass spectrometry and elemental analysis. All the triarylmethanes were tested and evaluated for their antiviral and antifungal activities. Compounds 3b, 3f, 3g and 3i exhibited highest antiviral activities against tobacco mosaic virus (TMV).

  一系列新型三芳基甲烷衍生物（3a-j）通过一锅法、两组分方法，在聚乙二醇（PEG-400）作为绿色溶剂的存在下，以50-60 °C的温度，通过各种富电子芳烃（1a-j）与多种醛（2a-j）的Friedel-Crafts烷基化反应合成，产率良好至优异（76-96 %）。它们的结构通过FT-IR、1H NMR、13C NMR、质谱和元素分析得到确认。所有三芳基甲烷均经过测试并评估了其抗病毒和抗真菌活性。化合物3b、3f、3g和3i对烟草花叶病毒（TMV）显示出最高的抗病毒活性。
• A facile iron-catalyzed dual C–C bond cleavage: an approach towards triarylmethanes
  作者：Dipankar Paul、Snehadrinarayan Khatua、Paresh Nath Chatterjee

  DOI：10.1039/c9nj00149b

  日期：——

  leaving groups perceived during the study enabled us to develop an application of the dual C–C bond breaking reaction for the synthesis of unsymmetrical triarylmethanes in a stepwise manner. To improve the synthetic utility, we have also fashioned a one-pot procedure to generate unsymmetrical triarylmethanes via sequential C–C bond breaking reactions. In addition to studying a novel dual C–C bond breaking

  已经开发出一种简便的铁催化双CC键裂解反应，涉及1,3-二羰基单元以及富电子和空间庞大的芳烃作为有效的基于碳的离去基团。使用一系列亲核试剂以良好或优异的产率合成对称的三芳基甲烷，详细研究了双CC键断裂反应的范围。我们发现成功分离了通过初始C sp 3 –C sp 3键裂解形成的反应中间体，并随后通过C sp 3 –C sp 2将中间体转化为最终产物的成功方法。键断裂。在研究过程中感知到的两个基于碳的离去基团的离去亲和力的显着差异使我们得以逐步开发出双CC键断裂反应用于不对称三芳基甲烷合成的方法。为了提高合成效用，我们还设计了一种一锅法，可通过顺序的C–C键断裂反应生成不对称的三芳基甲烷。除了研究新颖的双C–C键断裂反应并为机理提供线索外，该研究在合成对称且尤其是不对称的三芳基甲烷方面的应用也为当前的工作提供了价值。
• Development of Transition‐Metal‐Free Lewis Acid‐Initiated Double Arylation of Aldehyde: A Facile Approach Towards the Total Synthesis of Anti‐Breast‐Cancer Agent
  作者：Sanjay Singh、Rina Mahato、Pragya Sharma、Naveen Yadav、Nagaraju Vodnala、Chinmoy Kumar Hazra

  DOI：10.1002/chem.202104545

  日期：2022.3.7

  reported. This protocol features mild conditions, feedstock reagents, very low catalyst loading, remarkable scope (>85 examples) and gram-scale synthesis (TON=475). Moreover, several unexplored biologically active molecules for example, the antiparkinson agent, vibrindole A, turbomycin B and, total synthesis of an anti-breast-cancer agent is demonstrated. Control experiments and mechanistic studies

  报道了一种用于合成对称/不对称三芳基甲烷和二芳基甲烷的无过渡金属方法。该协议具有温和的条件、原料试剂、极低的催化剂负载、显着的范围（>85 个示例）和克级合成（TON=475）。此外，还展示了几种未开发的生物活性分子，例如抗帕金森剂、vibrindole A、涡轮霉素 B 和抗乳腺癌剂的全合成。还进行了对照实验和机理研究，以检测反应中间体和反应进程，以阐明可能的反应机理。
• Brønsted‐Acid‐Catalyzed One‐Pot Synthesis of β,β‐Diaryl Esters: Direct Regioselective Approach to Diverse Arrays of 3‐Aryl‐1‐indanone Cores
  作者：Pragya Sharma、Neha Taneja、Sanjay Singh、Chinmoy K. Hazra

  DOI：10.1002/chem.202202956

  日期：2023.1.9

  Three-component, solvent-dependent, Brønsted-acid-catalyzed reaction of benzaldehydes, silyl enolates and arene nucleophiles has been developed for the synthesis of potential drug candidate 3-aryl-1-indanones. This reaction features the formation of three C−C bonds, high regioselectivity in a one-pot strategy, broad substrate generality, facile scalability, high functional group tolerance and viable

  苯甲醛、甲硅烷基烯醇化物和芳烃亲核试剂的三组分、溶剂依赖性、Brønsted 酸催化反应已被开发用于合成潜在候选药物 3-aryl-1-indaniones。该反应的特点是形成三个 C-C 键，在一锅法策略中具有高区域选择性，广泛的底物通用性，易于扩展，高官能团耐受性和可行的底物。
• Friedel−Crafts Arylation Reactions of <i>N</i>-Sulfonyl Aldimines or Sulfonamidesulfones with Electron-Rich Arenes Catalyzed by FeCl₃·6H₂O: Synthesis of Triarylmethanes and Bis-heteroarylarylmethanes
  作者：Ponnaboina Thirupathi、Sung Soo Kim

  DOI：10.1021/jo1010137

  日期：2010.8.6

  The FeCl3 center dot 6H(2)O-catalyzed Friedel-Crafts arylation reactions of N-sulfonyl aldimines or sulfonamidesulfones with electron-rich arenes and heteroarenes, which lead to the formation of triarylmethanes and bis-heteroarylarylmethanes, are developed. The use of mild reaction conditions, low catalytic loading, high yield, and single step synthesis are the advantages of the present procedure.