14-(4-chloro-3-nitrophenyl)-14H-dibenzo[a,j]xanthene | 68828-13-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 14-(4-chloro-3-nitrophenyl)-14H-dibenzo[a,j]xanthene
• 英文别名: 2-(4-Chloro-3-nitrophenyl)-13-oxapentacyclo[12.8.0.03,12.04,9.017,22]docosa-1(14),3(12),4,6,8,10,15,17,19,21-decaene
• CAS: 68828-13-7
• 化学式: C₂₇H₁₆ClNO₃
• 分子量: 437.882
• InChiKey: UWNTYQUKNQDZJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  32
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-萘酚 、 4-氯-3-硝基苯甲醛 在 1-甲基吡咯烷-2-酮硫酸盐 作用下， 以 neat (no solvent) 为溶剂， 反应 0.13h， 以95%的产率得到14-(4-chloro-3-nitrophenyl)-14H-dibenzo[a,j]xanthene
  参考文献：
  名称：

  绿色条件下无环布朗斯台德酸性离子液体[H-NMP][HSO4]催化14-芳基-14H-二苯并[a,j]呫吨的环境友好和一锅法合成

  摘要：

  摘要 描述了一种方便、高效的直接制备 14-芳基-14 H-二苯并[a,j]-呫吨的方案。描述了 2-萘酚与各种芳香醛在催化量的 [H-NMP][HSO 4 ] 作为布朗斯台德酸性离子液体的存在下，在 110 °C 的无溶剂条件下缩合。该方法具有以下优点：反应后处理非常容易，催化剂循环顺畅，通过绿色一锅法催化高收率制备14-芳基-14H-二苯并[a,j]呫吨. 以极好的收率、高纯度和短反应时间获得了相应的产物。

  DOI：

  10.1016/j.crci.2013.08.003

文献信息

• Fe2+ supported on hydroxyapatite-core–shell-γ-Fe2O3 nanoparticles: Efficient and recyclable green catalyst for the synthesis of 14-aryl-14H-dibenzo[a,j]xanthene derivatives
  作者：Hakimeh Sadat Haeri、Sobhan Rezayati、Eshagh Rezaee Nezhad、Hamed Darvishi

  DOI：10.1007/s11164-015-2318-5

  日期：2016.5

  electron microscopy, and vibrating sample magnetometry spectra. Then, γ -Fe2O3–HAp-Fe2+ NPs were used as an efficient, reusable and heterogeneous nanocatalyst for one-pot synthesis of 14-aryl-14H-dibenzo[a,j]xanthenes via the one-pot condensation reaction of arylaldehydes and 2-naphthol under solvent-free conditions in good to excellent yields. This procedure has a lot of advantages such as very easy

  在这项工作中，铁2+支撑在羟基磷灰石的核-壳- γ -Fe 2 ö 3纳米颗粒（ γ -Fe 2 ö 3 -HAp -铁2+的NP）已被制备和表征通过傅里叶变换红外光谱，X-射线衍射，透射电子显微镜，扫描电子显微镜和振动样品磁强光谱。然后， γ -Fe 2 O 3 -HAp-Fe 2+通过无溶剂条件下芳基醛和2-萘酚的一锅缩合反应，NPs被用作一种高效，可重复使用的多相纳米催化剂，用于一锅合成14-芳基-14H-二苯并[a，j]黄嘌呤。高产。该方法具有许多优点，例如非常容易的反应条件，操作简单，反应时间短，产率高以及通过避免有毒的常规催化剂和溶剂而具有绿色方面。此外， γ -Fe 2 O 3 -HAp-Fe 2+ NPs易于从反应混合物中回收，可以重复使用七次而不会损失活性。
• Convenient Synthesis of 14-Aryl-14-H-dibenzo[<i>a,j</i>]xanthenes Catalyzed by Acyclic Brønsted Acidic Ionic Liquid [H-NMP]⁺[HSO₄]⁻under Microwave Irradiation
  作者：Hossein Naeimi、Zahra Sadat Nazifi

  DOI：10.1002/jccs.201300019

  日期：2013.9

  14‐aryl‐14‐H‐dibenzo[a,j]xanthenes through condensation of β‐naphthol with various aromatic aldehydes in the presence of the catalytic amount of [H—NMP]+[HSO4]− under microwave irradiation was described. This method has the advantages such as; very easy reaction workup, absolute separation of catalyst from the reaction mixture and smooth recyclability of catalyst. In this reaction 14‐aryl‐14‐H‐dibenzo[a,j]xanthenes

  用于直接制备14 -芳基- 14-H二苯并有效的方法[一，J ]呫吨通过与[H-NMP]的催化量的存在的各种芳香醛β萘酚的缩合+ [HSO 4 ] -描述了在微波照射下。该方法具有以下优点：非常简单的反应后处理，催化剂与反应混合物的绝对分离以及催化剂的可循环利用性。在该反应中，通过绿色和一锅法，以优异的收率和较短的反应时间获得了所需的产物14-芳基-14-H-二苯并[ a，j ]氧杂蒽。
• FeCl3-Catalyzed Condensation of 2-Naphthol and Aldehydes under Solvent-Free Reaction Conditions: An Efficient and Green Alternative for the Synthesis of 14-Aryl(Alkyl)-14-H-dibenzo[a, j]xanthenes
  作者：Bo Wang、Pinghua Li、Yicheng Zhang、Lei Wang

  DOI：10.1002/cjoc.201190022

  日期：2010.12

  An iron‐catalyzed condensation of 2‐naphthol with aldehydes has been described. In the presence of a catalytic amount of iron(III) chloride (5 mol%), the condensation reaction of 2‐naphthol and aldehydes underwent smoothly to generate the corresponding products in good to excellent yields under base‐, acid‐, ligand‐, additive‐, and solvent‐free reaction conditions.

  已经描述了2-萘酚与醛的铁催化缩合。在催化量的氯化亚铁（III）（5 mol％）的存在下，2-萘酚与醛的缩合反应顺利进行，从而在碱，酸，配体，无添加剂和无溶剂的反应条件。
• Design, Synthesis and Antiviral Potential of 14-Aryl/Heteroaryl-14H-dibenzo[a,j]xanthenes Using an Efficient Polymer-Supported Catalyst
  作者：Kalla Reddi Mohan Naidu、Balam Satheesh Krishna、Mungara Anil Kumar、Palanisamy Arulselvan、Shaik Ibrahim Khalivulla、Ola Lasekan

  DOI：10.3390/molecules17067543

  日期：——

  Polyethyleneglycol bound sulfonic acid (PEG-OSO3H), a chlorosulphonic acid-modified polyethylene glycol was successfully used as an efficient and eco-friendly polymeric catalyst in the synthesis of 14-aryl/heteroaryl-14H-dibenzo[a,j]xanthenes obtained from the reaction of 2-naphthol and carbonyl compounds under solvent-free conditions with short reaction times and excellent yields. The biological properties of these synthesized title compounds revealed that compounds 3b, 3c, 3f and 3i showed highly significant anti-viral activity against tobacco mosaic virus.

  聚乙二醇结合磺酸（PEG-OSO3H）是一种氯磺酸改性聚乙二醇，被成功用作一种高效、环保的聚合物催化剂，用于在无溶剂条件下合成由 2-萘酚和羰基化合物反应得到的 14-芳基/异芳基-14H-二苯并[a,j]呫吨，反应时间短，收率高。这些合成的标题化合物的生物学特性表明，化合物 3b、3c、3f 和 3i 对烟草花叶病毒具有非常显著的抗病毒活性。
• Sulfonated diatomite as heterogeneous acidic nanoporous catalyst for synthesis of 14-aryl-14-H-dibenzo[a,j]xanthenes under green conditions
  作者：Hossein Naeimi、Zahra Sadat Nazifi

  DOI：10.1016/j.apcata.2014.03.012

  日期：2014.5

  Sulfonic acid functionalized diatomite afforded diatomite-SO3H as an efficient heterogeneous solid acid nanoporous. The resulting immobilized catalysts have been successfully used in the synthesis of 14-aryl-14-H-dibenzo[a,j]xanthenes under solvent free conditions. This procedure has a lot of advantages such as very easy reaction conditions, recyclable heterogeneous acidic catalyst, natural catalyst, absence of any tedious workup or purification and much milder method. The corresponding products have been obtained in excellent yields, high purity and short reaction times. (C) 2014 Elsevier B.V. All rights reserved.