12-(5-bromo-2-hydroxyphenyl)-9,9-dimethyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one | 1187642-06-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: 12-(5-bromo-2-hydroxyphenyl)-9,9-dimethyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one
• 英文别名: 12-(5-bromo-2-hydroxyphenyl)-9,9-dimethyl-10,12-dihydro-8H-benzo[a]xanthen-11-one
• CAS: 1187642-06-3
• 化学式: C₂₅H₂₁BrO₃
• 分子量: 449.344
• InChiKey: AVMONSBRSVICLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  29
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5,5-二甲基-1,3-环己二酮 、 2-萘酚 、 5-溴水杨醛 在 thioglycolic acid doped on Fe₃O₄ nanomagnetic particles coated with tris(hydroxymethyl)aminomethane 作用下， 以 neat (no solvent) 为溶剂， 反应 0.17h， 以92%的产率得到12-(5-bromo-2-hydroxyphenyl)-9,9-dimethyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one
  参考文献：
  名称：

  一种新型可重复使用的 Fe3O4@THAM-CH2CH2-SCH2CO2H 磁性纳米催化剂的合成和表征，用于在绿色条件下高效制备呫吨和 3-氨基异恶唑

  摘要：

  在本研究中，描述了一种新型巯基乙酸掺杂在三（羟甲基）氨基甲烷 (THAM) 和 1,2-二氯乙烷涂层的Fe 3 O 4纳米磁性颗粒上的合成和催化应用。形态、结构和理化性质已通过几种分析方法阐明，如 FT-IR、TEM、VSM、XRD、TGA 和 FE-SEM。这种纳米催化剂已成功用作多相酸催化剂，用于合成多种取代的具有生物学重要性的呫吨和 3-氨基异恶唑衍生物。这种催化剂不需要我们长时间反应和从产物中分离硬催化剂，并且可以很容易地用外部磁铁连续 8 次回收，而其催化性能没有显着下降。 图形摘要

  DOI：

  10.1007/s11164-021-04558-9

文献信息

• An efficient one-pot synthesis of tetrahydrobenzo[a]xanthene-11-one and diazabenzo[a]anthracene-9,11-dione derivatives under solvent free condition
  作者：Ganesh Chandra Nandi、Subhasis Samai、Ram Kumar、M.S. Singh

  DOI：10.1016/j.tet.2009.06.024

  日期：2009.8

  Indium(III) chloride catalyzed one-pot synthesis of 12-aryl/alkyl-8,9,10,12-tetrahydrobenzo[a]xanthene-11-one and 8,10-dimethyl-12-aryl-8,12-dihydro-7-oxa-8,10-diazabenzo[a]anthracene-9,11-dione derivatives have been achieved by three component cyclocondensation of aldehydes, β-naphthol and cyclic 1,3-dicarbonyl compounds under solvent free condition in high yields. P2O5 too has been found as an effective

  氯化铟（III）催化一锅合成12-芳基/烷基-8,9,10,12-四氢苯并[ a ]氧杂蒽-11-one和8,10-二甲基-12-芳基-8,12-二氢通过醛，β-萘酚和环状1,3-二羰基化合物在无溶剂条件下的三组分环缩合，可以高产率获得-7-氧杂-8,10-二氮杂苯并[ a ]蒽-9,11-二酮衍生物。还发现P 2 O 5是实现该转化的有效催化剂。
• Nanoparticle Silica Supported Sulfuric Acid (NPs SiO₂-H₂SO₄): A Solid Phase Acidic Catalyst for the One-Pot Synthesis of Benzo[a]Xanthene-11-One Derivatives
  作者：Bahareh Sadeghi、Alireza Hassanabadi、Elahe Taghvatalab

  DOI：10.3184/174751911x13230223609418

  日期：2011.12

  The reaction between aromatic aldehydes, dimedone (5,5-dimethyl-1,3-cyclohexane dione) and 2-naphthol catalysed by nanoparticle silica supported sulfuric acid (NPs SiO₂-H₂SO₄) in CH₂Cl₂ as a solvent at room temperature provided a simple and efficient one-pot route for the synthesis of benzo[a]xanthene-11-one derivatives in high yield. Benzoxanthenes are important heterocycles because of their antiviral, anti-inflammatory and antibacterial activities.

  室温下，在以 CH2Cl2 为溶剂的纳米颗粒二氧化硅（NPs SiO2-H2SO4）的催化下，芳香醛、二酮（5,5-二甲基-1,3-环己烷二酮）和 2-萘酚发生反应，为高产率合成苯并[a]氧杂蒽-11-酮衍生物提供了一条简单高效的一锅法路线。苯并氧杂蒽因具有抗病毒、抗炎和抗菌活性而成为重要的杂环化合物。
• Facile One-Pot Synthesis of Tetrahydrobenzo[a]xanthene-11-one and Aryl-14<i>H</i>-dibenzo[a.j]xanthene
  作者：Ramin Ghorbani-Vaghei、Seyedeh Mina Malaekehpoor

  DOI：10.1080/00304948.2010.514802

  日期：2010.10.4
• An efficient method for the synthesis of functionalized 4H-chromenes as optical sensor for detection of Fe3+ in ethanol
  作者：Zohreh Kheilkordi、Ghodsi Mohammadi Ziarani、Negar Lashgari、Alireza Badiei

  DOI：10.1016/j.poly.2019.03.042

  日期：2019.7

  An efficient method for the synthesis of functionalized 4H-chromenes via a one-pot three-component condensation reaction of a 2-hydroxybenzaldehyde with an active methylene compound and a carbon-based nucleophile in the presence of SrFe12O19 as catalyst under solvent-free at 80 degrees C condition has been described. SrFe12O19 was an efficient, green, and reusable magnetic nanoparticles as heterogeneous catalyst with the average particles size of 70 nm which can be recycled and readily separated from the reaction mixture using an external magnet. High product yields, simple work-up procedure, solvent-free conditions and characterization of the sensing properties of compound 4a for detection of Fe3+ ion are the main advantages of this procedure. The sensing ability of compound 4a was examined upon addition of a wide variety of cations both visually and by UV-Vis spectroscopy. The increase in UV-Vis absorbance was linearly proportional to the concentration of Fe3+ with a detection limit of 1.0 x 10(-7) M. Moreover, the chemosensor exhibited an obvious color change from white to yellow in the presence of Fe3+ in EtOH solution. (C) 2019 Elsevier Ltd. All rights reserved.