14-phenyl-14H-dibenzo[a,i]xanthene-8,13-dione | 1219933-73-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 14-phenyl-14H-dibenzo[a,i]xanthene-8,13-dione
• 英文别名: 2-Phenyl-13-oxapentacyclo[12.8.0.03,12.04,9.016,21]docosa-1(14),3(12),4,6,8,10,16,18,20-nonaene-15,22-dione；2-phenyl-13-oxapentacyclo[12.8.0.03,12.04,9.016,21]docosa-1(14),3(12),4,6,8,10,16,18,20-nonaene-15,22-dione
• CAS: 1219933-73-9
• 化学式: C₂₇H₁₆O₃
• 分子量: 388.422
• InChiKey: NQKPMSMBKMZYDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  30
• 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：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-羟基-1,4-萘醌 、 苯甲醛 、 2-萘酚 在 nickel oxide supported on silica core-shell nanoparticles 作用下， 以 乙醇 为溶剂， 以96 %的产率得到14-phenyl-14H-dibenzo[a,i]xanthene-8,13-dione
  参考文献：
  名称：

  可重复使用的SiO2@NiO核壳纳米颗粒催化高效合成14-芳基-14H-二苯并[a,i]呫吨-8, 13-二酮衍生物

  摘要：

  二氧化硅负载氧化镍催化取代芳香醛与2-萘酚/2,7-二羟基萘和2-羟基萘-1,4-二酮的多元缩合反应

  DOI：

  10.1080/00397911.2023.2261571

文献信息

• Efficient one-pot syntheses of dibenzo[<i>a</i>,<i>i</i>]xanthene-diones and evaluation of their antioxidant activity
  作者：Jitender M. Khurana、Ankita Chaudhary、Anshika Lumb、Bhaskara Nand

  DOI：10.1139/v2012-033

  日期：2012.9

  Facile and convenient procedures for the synthesis of dibenzo[a,i]xanthene-diones have been described. The process employs one-pot condensation of aldehydes, 2-hydroxynaphthalene-1,4-dione, and 2-naphthol/2,7-dihydroxynaphthalene/2,6-dihydroxynaphthalene using catalytic sulfuric acid in water under reflux. Task-specific ionic liquid, 1-butyl-3-methylimidazolium hydrogen sulfate ([bmim]HSO₄), has also been found to be an effective catalyst for this transformation. The protocols defined herein prove to be efficient in terms of high yields, operational simplicity, easy workup, and short reaction time. Also, these compounds were screened for antioxidant activity by 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging assay.

  已经描述了合成二苯并[a,i]蒽醌二酮的简便和方便的程序。该过程采用在水回流下使用催化硫酸的醛、2-羟基-1,4-萘醌和2-萘酚/2,7-二羟基萘/2,6-二羟基萘的一锅法缩合。特定任务的离子液体，1-丁基-3-甲基咪唑硫酸氢盐([bmim]HSO₄)，也被发现是这种转化的有效催化剂。此处定义的协议在收率较高、操作简单、易于后处理和反应时间短方面证明是有效的。此外，这些化合物通过2,2-二苯基-1-苦基肼自由基清除剂(2,2-diphenyl-1-picrylhydrazyl, DPPH)进行了抗氧化活性的筛选。

• Nano-Fe3O4 -encapsulated silica particles bearing sulfonic acid groups as a magnetically separable catalyst for the green and efficient synthesis of 14-aryl-14H-dibenzo[a,i]xanthene-8,13-dione derivatives
  作者：Mohammad Ali Ghasemzadeh、Mina Azimi-Nasrabad

  DOI：10.1007/s11164-015-2073-7

  日期：2016.2

  efficient and environmentally friendly ("green") method for one-pot synthesis of xanthene derivatives was developed in the presence of Fe3O4@SiO2–SO3H nanoparticles. The functionalization of silica-coated Fe3O4 magnetite nanoparticles (Fe3O4@SiO2) using chlorosulfonic acid was afforded by nano-Fe3O4 encapsulated-silica particles bearing sulfonic acid (Fe3O4@SiO2–SO3H) that could be applied as a reusable

  在这项研究中，开发了一种在Fe 3 O 4 @SiO 2 -SO 3 H纳米粒子存在下一锅法合成x吨衍生物的高效环保方法。带有磺酸（Fe 3 O 4 @SiO 2 –SO ）的纳米Fe 3 O 4包封二氧化硅颗粒可实现使用氯磺酸对二氧化硅包覆的Fe 3 O 4磁铁矿纳米颗粒（Fe 3 O 4 @SiO 2）进行功能化。3H）可以用作可重复使用和有效的多相纳米催化剂。在回流条件下进行2-羟基-1，4-萘醌，β-萘酚和醛的多组分反应，得到一些14-芳基-14H-二苯并[a，i]]吨-8，13-二酮衍生物。该方法具有环境友好，收率高，反应时间短，纯化简单和催化剂分离简便等优点，是一种简便的方法。Fe 3 O 4 @SiO 2 –SO 3H可以使用外部磁体轻松回收，并且可以重复使用几次，而不会显着降低反应活性。通过振动样品磁力法（VSM），傅立叶变换红外（FT-IR）光谱，扫描电子显微镜（SEM）
• Phosphoric acid supported on alumina (H3PO4/Al2O3) as an efficient and reusable catalyst for the one-pot synthesis of benzoxanthene pigments
  作者：Hamid Reza Shaterian、Kobra Azizi、Nafiseh Fahimi

  DOI：10.1007/s11164-013-1047-x

  日期：2014.4

  Phosphoric acid supported on alumina (H3PO4/Al2O3) is an efficient catalyst for the catalytic multi-component condensation reaction and a wide variety of syntheses of benzoxanthene pigments in good yields. The remarkable features of this new procedure are high conversions, shorter reaction times, cleaner reaction, and simple experimental and work-up procedures.

  负载于氧化铝上的磷酸（H3PO4/Al2O3）是一种高效的催化剂，可用于催化多组分缩合反应及一系列在良好产率下合成苯并二氧杂蒽类色素的合成中。该新方法的显著特点包括高转化率、较短的反应时间、更纯净的反应过程及简单易行的实验和后处理步骤。
• The first catalytic application of copper aluminate nanoparticles in C–C and C–O coupling reaction: green synthesis of some new α‐lapachone derivatives
  作者：Bahareh Abdolpour Mori、Saeed Khodabakhshi、Sanaz Tajik、Mojtaba Baghernejad、Amir Yadegari

  DOI：10.1007/s00706-016-1692-z

  日期：2016.10

  the multicomponent organic synthesis. The CuAl2O4 NPs was prepared and characterized by XRD, SEM, and TEM for this purpose and applied in the green synthesis of pyranonaphthoquinones (α-lapachone derivatives) under solvent-free conditions. The nanocatalyst can be recycled and reused for four times. Graphical abstract

  摘要这是铝酸铜纳米颗粒（CuAl 2 O 4 NPs）作为多组分有机合成的有效催化剂的首次应用。为此，制备了CuAl 2 O 4 NPs，并通过XRD，SEM和TEM对其进行了表征，并将其用于无溶剂条件下的吡喃并萘醌（α-lapachone衍生物）的绿色合成。纳米催化剂可以循环使用四次。 图形概要
• Polystyrene-supported GaCl3 as a highly efficient and reusable heterogeneous Lewis acid catalyst for the three-component synthesis of benzoxanthene derivatives
  作者：Ali Rahmatpour

  DOI：10.1007/s00706-013-0931-9

  日期：2013.8

  procedure utilizing polystyrene-supported gallium trichloride as a highly active and eco-friendly heterogeneous Lewis acid catalyst. This reaction was also extended to the preparation of 14-aryl-2-hydroxy-13H-dibenzo[a,i]xanthene-8,13(14H)-diones. The experimental and work-up procedure is very simple and the catalyst can be easily separated from the reaction mixture and reused several times in subsequent

  摘要基于萘醌的黄嘌呤，特别是14-芳基-13 H-二苯并[ a，i ] x吨-8,13 （14 H）-二酮和12-芳基-2,3,4,12-四氢-1 H-苯并[通过使用聚苯乙烯负载的三氯化镓作为高活性和生态友好型非均质路易斯酸催化剂，通过简单，温和和有效的三组分偶联程序，以良好至优异的收率获得了b ]吨蒽-1,6,11-三酮。 。该反应还扩展到制备14-芳基-2-羟基-13 H-二苯并[ a，i ]吨蒽-8,13（14 H）-diones。实验和后处理程序非常简单，催化剂可以轻松地从反应混合物中分离出来，并在后续反应中重复使用几次。 图形概要