14-(2-fluorophenyl)-14H-dibenzo[a,j]xanthene | 66595-95-7

• 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-(2-fluorophenyl)-14H-dibenzo[a,j]xanthene
• 英文别名: 2-(2-fluorophenyl)-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: 66595-95-7
• 化学式: C₂₇H₁₇FO
• 分子量: 376.43
• InChiKey: KVTKIYCLPFYCSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  29
• 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：
  9.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-氟苯甲醛 、 2-萘酚 在 五氯化铌 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以95%的产率得到14-(2-fluorophenyl)-14H-dibenzo[a,j]xanthene
  参考文献：
  名称：

  Efficient one-pot synthesis of 14-aryl-14H-dibenzo[a,j]xanthene derivatives promoted by niobium pentachloride

  摘要：

  本文描述了一种简单高效的方法，通过在铌五氯化物存在下，将2-萘酚与芳基醛一锅法缩合合成14-芳基-14H-二苯并[a,j]黄芩烷衍生物。反应在常温下使用25摩尔%的NbCl5进行，反应时间合适，产率优异。

  DOI：

  10.2478/s11696-014-0597-8

文献信息

• A simple and efficient one-pot bis-bromine-1,4-diazabicyclo [2.2.2]octane (Br2-DABCO) catalyzed synthesis of 14-aryl-14H-dibenzo[a,j]xanthenes under solvent-free conditions
  作者：Hassan Ghasemnejad-Bosra、Mehdi Forouzani

  DOI：10.1515/hc.2011.020

  日期：2011.1.1

  Abstract Bis-bromine-1,4-diazabicyclo[2.2.2]octane (Br2-DABCO) is an efficient, readily available, and reusable catalyst for the synthesis of 14-aryl-14H-dibenzo[a,j]xanthenes 3 by condensation of β-naphthol 2 and aldehydes 1. This reaction under solvent-free conditions is very simple, affording good to excellent yields of products.

  摘要 双溴 1,4-二氮杂双环 [2.2.2] 辛烷 (Br2-DABCO) 是一种高效、易得且可重复使用的催化剂，用于合成 14-芳基-14H-二苯并[a,j]呫吨 3 β-萘酚 2 与醛的缩合反应 1. 该反应在无溶剂条件下非常简单，产品收率良好。
• Sulfonated starch nanoparticles: An effective, heterogeneous and bio-based catalyst for synthesis of 14-aryl-14- H -dibenzo[a,j]xanthenes
  作者：Javad Safari、Pegah Aftabi、Majid Ahmadzadeh、Masoud Sadeghi、Zohre Zarnegar

  DOI：10.1016/j.molstruc.2017.02.095

  日期：2017.8

  Abstract In recent years, biodegradable polymer based nanoparticles have attracted wide attention for the synthesis of high-performance and green catalytic species. Polymeric nanoparticles used for catalytic processes must be biocompatible and biodegradable. The objective of this study is to fabricate starch nanoparticles from native starch and preparation of sulfonated starch nanoparticles (HO3S-SNPs)

  摘要 近年来，可生物降解聚合物基纳米粒子在合成高性能绿色催化物种方面受到广泛关注。用于催化过程的聚合物纳米粒子必须具有生物相容性和生物可降解性。本研究的目的是从天然淀粉制备淀粉纳米粒子，并制备磺化淀粉纳米粒子 (HO3S-SNPs) 作为酸性纳米催化剂在无溶剂条件下合成 14-芳基-14-H-二苯并 [a,j] 呫吨. 该程序具有许多优点，例如非常容易的反应条件、低成本的生产和天然催化剂以及没有任何繁琐的后处理或纯化。以优异的收率、高纯度和短反应时间获得了相应的产物。
• Synthesis and characterization of a novel Brönsted acidic dicationic ionic liquid based on piperazine and its application in the one-pot synthesis of various xanthenes under solvent-free conditions
  作者：Zainab Ehsani-Nasab、Ali Ezabadi

  DOI：10.1007/s11164-022-04666-0

  日期：2022.3

  In this paper, an interesting Brönsted acidic dicationic ionic liquid based on piperazine was prepared via two-step synthesis. The structure of the dicationic ionic liquid (DIL) was confirmed with various techniques including Fourier transform infrared spectroscopy (FT-IR), Proton NMR (1H NMR), Carbon-13 NMR (13C NMR), mass spectroscopy (MS), acid–base titration as well as Hammett acidity function

  在本文中，通过两步合成制备了一种有趣的基于哌嗪的 Brönsted 酸性双阳离子离子液体。双阳离子离子液体 (DIL) 的结构通过多种技术确认，包括傅里叶变换红外光谱 (FT-IR)、质子 NMR ( 1 H NMR)、Carbon-13 NMR ( 13 C NMR)、质谱 (MS)、酸碱滴定和哈米特酸度函数。在呫吨合成中检测了这种新型布朗斯台德酸性 DIL 的催化活性。产品收率高、反应时间短、催化剂易于回收和再利用以及不使用有机溶剂是开发过程的一些优点。
• Preparation and Characterization of a Novel Glycine-based Ionic Liquid and its Application in the Synthesis of Xanthenediones and Dihydropyrimidones in Water
  作者：Ali Ezabadi、Masoumeh Salami

  DOI：10.2174/1570178619666220324122621

  日期：2022.12

  A novel amino acid ionic liquid was synthesized, characterized, and approved as an efficient and recyclable catalyst for synthesizing xanthenediones and DHPMs in water at reflux temperature.

  The ionic liquid was synthesized by a two-step method. In the first step, pyridine- N-sulfonic acid was prepared by the reaction of pyridine with chlorosulfonic acid. In the second step, the reaction of as-prepared ionic liquid with glycine in water afforded the desired amino acid ionic liquid. Then, the ionic liquid was fully characterized by FT-IR, 1H NMR, 13C NMR, MS, TG/DTG, and Hammett acidity function.

  We disclose a new strategy to incorporate glycine as the amino acid-based cation in the ionic liquid structure. The prepared IL exhibited remarkable catalytic activity in synthesizing xanthendiones and DHPMs in water at reflux temperature.

  We have developed a green and efficient amino acid ionic liquid to synthesize xanthenediones in water at reflux temperature. The advantage of this protocol is highlighted by the novelty of the ionic liquid, using H2O as the solvent, simple work-up, high yields, and short reaction times.

  目的和目标： 合成了一种新型氨基酸离子液体，并对其进行了表征。 回流温度下在水中合成呫吨和 DHPMs 的高效、可回收催化剂。 回流温度下合成呫吨和 DHPMs 的高效、可回收催化剂。 材料和方法： 离子液体采用两步法合成。第一步，通过吡啶与氯磺酸反应制备吡啶 N- 磺酸是由吡啶与氯磺酸反应制备的。第二步 第二步，将制备的离子液体与甘氨酸在水中反应，得到所需的氨基酸离子液体。 液。然后，离子液体通过傅立叶变换红外光谱、1H NMR、13C NMR、质谱、TG/DTG 和 Hammett 酸度函数进行全面表征。 结果： 我们揭示了在离子液体结构中加入甘氨酸作为氨基酸阳离子的新策略。 液结构。所制备的离子液体在回流温度下于水中合成 xanthendiones 和 DHPMs 的催化活性。 结论 我们开发了一种绿色高效的氨基酸离子液体，用于在回流温度下在水中合成呫吨二酮类化合物 的方法。该方案的优势突出表现在离子液体的新颖性、使用 H2O 作为溶剂、操作简单 离子液体的新颖性、使用 作为溶剂、操作简单、产率高和反应时间短等优点。
• Silica sulfuric acid: A simple, efficient, and reusable heterogeneous catalyst for the one-pot synthesis of aryl-14H-dibenzo[a,j]xanthenes under conventional heating and solvent-free conditions
  作者：Raveendra K. Hunnur、B. Sunilkumar、P. S. Kumar、N. Srinivasulu、R. H. Udupi、V. Hima bindu

  DOI：10.1007/s10593-008-0035-3

  日期：2008.2

  A novel approach towards the one-pot synthesis of aryl-14H-dibenzo[a,j]xanthenes is described from a known reaction between substituted aldehydes and beta-naphthol in the presence of heterogeneous catalyst silica sulfuric acid under conventional heating as well as solvent-free conditions to afford good to excellent yields. The catalyst is reusable; it can be used several times without any decrease in the product yield.