12-(4-methoxyphenyl)-9,9-dimethyl-2-hydroxy-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one | 1352090-33-5

• 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-(4-methoxyphenyl)-9,9-dimethyl-2-hydroxy-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one
• 英文别名: 2-hydroxy-12-(4-methoxyphenyl)-9,9-dimethyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one；2-hydroxy-12-(4-methoxyphenyl)-9,9-dimethyl-10,12-dihydro-8H-benzo[a]xanthen-11-one
• CAS: 1352090-33-5
• 化学式: C₂₆H₂₄O₄
• 分子量: 400.474
• InChiKey: ISFPPMLCNKGXQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  30
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  12-(4-methoxyphenyl)-9,9-dimethyl-2-hydroxy-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one 、 4-叠氮基-7-氯喹啉 、 3-溴丙炔 在 copper(ll) sulfate pentahydrate 、 potassium carbonate 、 sodium ascorbate 作用下， 反应 0.58h， 以88%的产率得到2-((1-(7-chloroquinolin-4-yl)-1H-1,2,3-triazol-4-yl)methoxy)-12-(4-methoxyphenyl)-9,9-dimethyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one
  参考文献：
  名称：

  Efficient One Pot Synthesis of Xanthene-Triazole-Quinoline/Phenyl Conjugates and Evaluation of their Antimicrobial Activity

  摘要：

  Novel xanthene-triazole-quinoline/phenyl conjugates were synthesized by eco-friendly one pot three-component condensation of 12-aryl-2-hydroxy-tetrahydrobenzo[a]xanthene-11-one, propargyl bromide and 4-azido-7-chloroquinoline/phenyl azide using polyethylene glycol (PEG-400) as a reaction medium with an aim to explore their effect on the in vitro growth of microorganisms causing microbial infection. All newly synthesized xanthene-triazole-quinoline/ phenyl conjugates were fully characterized and were evaluated for in vitro antibacterial and antifungal activity. Antimicrobial activity was evaluated against nine microbial strains. All compounds showed good Gram positive antibacterial and antifungal activity. One of the compounds showed best antibacterial and antifungal activity. Further, binding mode of this compound at the active site of enzyme topoisomerase II DNA gyrase B has also been investigated.

  DOI：

  10.5935/0103-5053.20140095
• 作为产物：
  描述：

  2,7-二羟基萘 、 4-甲氧基苯甲醛 、 5,5-二甲基-1,3-环己二酮 在 Zr-MCM-41 作用下， 以 neat (no solvent) 为溶剂， 反应 0.2h， 以90%的产率得到12-(4-methoxyphenyl)-9,9-dimethyl-2-hydroxy-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one
  参考文献：
  名称：

  使用 Zr-MCM-41 催化剂快速高效地一锅法合成 12-Aryl-8,9,10,12-四氢苯并[a]xanthene-11-ones

  摘要：

  摘要 开发了一种新的绿色方案，用于通过二甲酮、萘酚和萘酚的三组分一锅缩合反应合成 12-芳基-8,9,10,12-四氢苯并[a]xanthen-11-ones。在无溶剂条件下，在 80 °C 下使用 Zr-MCM-41 纳米反应器作为可重复使用的新型催化剂制备芳香醛。在邻位、间位或对位含有吸电子和给电子取代基的各种芳族醛显示出相同的产物形成效率，产率从好到极好。操作简单、反应条件温和、速率提高、环境友好、纯产品的高分离产率以及通过非色谱方法纯化产品是此处介绍的协议的显着优势。催化剂可以回收再利用，而不会显着降低其活性。图形概要

  DOI：

  10.1080/00397911.2014.958784

文献信息

• Rapid and Efficient One-Pot Green Synthesis of 12-Aryl-8,9,10,12-tetrahydrobenzo[<i>a</i>]xanthene-11-ones Using Zr-MCM-41 Catalyst
  作者：Abolfazl Olyaei、Mona Ghodrat Alidoust

  DOI：10.1080/00397911.2014.958784

  日期：2015.1.2

  Abstract A new green protocol has been developed for the synthesis of 12-aryl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-ones via a three-component, one-pot condensation reaction of dimedone, naphthols, and aromatic aldehydes using Zr-MCM-41 nanoreactors as a reusable and novel catalyst at 80 °C under solvent-free conditions. Various aromatic aldehydes containing electron-withdrawing and electron-donating

  摘要 开发了一种新的绿色方案，用于通过二甲酮、萘酚和萘酚的三组分一锅缩合反应合成 12-芳基-8,9,10,12-四氢苯并[a]xanthen-11-ones。在无溶剂条件下，在 80 °C 下使用 Zr-MCM-41 纳米反应器作为可重复使用的新型催化剂制备芳香醛。在邻位、间位或对位含有吸电子和给电子取代基的各种芳族醛显示出相同的产物形成效率，产率从好到极好。操作简单、反应条件温和、速率提高、环境友好、纯产品的高分离产率以及通过非色谱方法纯化产品是此处介绍的协议的显着优势。催化剂可以回收再利用，而不会显着降低其活性。图形概要
• Synthesis and in vitro evaluation of antioxidant activity of diverse naphthopyranopyrimidines, diazaanthra[2,3-d][1,3]dioxole-7,9-dione and tetrahydrobenzo[a]xanthen-11-ones
  作者：Jitender M. Khurana、Anshika Lumb、Ankita Chaudhary、Bhaskara Nand

  DOI：10.1039/c2ra22406b

  日期：——

  A green and efficient one pot three component protocol has been developed for the synthesis of naphthopyranopyrimidines, diazaanthra[2,3-d][1,3]dioxole-7,9-dione and tetrahydrobenzo[a]xanthen-11-ones in PEG-400 catalyzed by alum (KAl(SO4)2·12H2O). Single crystal X-ray diffraction studies have been performed for naphthopyranopyrimidine (5). The synthesized compounds were screened for in vitro antioxidant activity by DPPH scavenging assay and compounds 3 and 4 manifested profound antioxidant potential.

  在明矾（KAl(SO4)2-12H2O）的催化下，开发了一种在 PEG-400 中合成萘并吡喃嘧啶、二氮杂蒽并[2,3-d][1,3]二恶茂-7,9-二酮和四氢苯并[a]氧杂蒽-11-酮的绿色高效的一锅三组分方案。对萘并吡喃嘧啶 (5) 进行了单晶 X 射线衍射研究。通过 DPPH 清除试验对合成的化合物进行了体外抗氧化活性筛选，结果表明化合物 3 和 4 具有很强的抗氧化潜力。
• A new green approach for the synthesis of 12-aryl-8,9,10,12-tetrahydrobenzo[a]xanthene-11-one derivatives using task specific acidic ionic liquid [NMP]H2PO4
  作者：Harjinder Singh、Sudesh Kumari、Jitender M. Khurana

  DOI：10.1016/j.cclet.2014.05.014

  日期：2014.10

  involving multicomponent condensation reactions of substituted aromatic aldehydes with 2,7-dihydroxynaphthalene/2-naphthols/2,6-dihydroxynaphthlene and cyclic 1,3-dicarbonyl compounds in task specific acidic ionic liquid [NMP]H 2 PO 4 at 80 °C. This protocol has proved to be efficient in terms of good yields, operational simplicity, easy workup, recyclability of reaction medium/catalyst, and short reaction

  摘要通过一种方便，环境友好的方法合成了12-芳基8,9,10,12-四氢苯并[a] x吨-11-酮衍生物，该过程涉及取代的芳族醛与2,7-二羟基萘/ 2-萘的多组分缩合反应。任务特定的酸性离子液体[NMP] H 2 PO 4在80°C下的/ 2,6-二羟基萘和环状1,3-二羰基化合物。已经证明该方案在高产率，操作简单，易于后处理，反应介质/催化剂的可回收性以及较短的反应时间方面是有效的。
• An efficient and convenient approach for the synthesis of novel 2-hydroxy-12-aryl-8,9,10,12-tetrahydrobenzo[a]xanthene-11-ones using p-toluenesulfonic acid in ethanol and ionic liquid
  作者：Jitender M. Khurana、Bhaskara Nand、Sneha

  DOI：10.1002/jhet.661

  日期：2011.11

  A novel series of 2‐hydroxy‐12‐aryl‐8,9,10,12‐tetrahydrobenzo[a]xanthene‐11‐ones were synthesized by the one‐pot multicomponent condensation of 2,7‐dihydroxynaphthalene, aromatic aldehydes, and cyclic 1,3‐dicarbonyl compounds in the presence of a catalytic amount of p‐toluenesulfonic acid in ethanol and in ionic liquid butyl methyl imidazolium tetrafluroborate ([bmim]BF4). The newly developed protocol

  通过2,7-二羟基萘，芳族醛和环的单锅多组分缩合反应合成了一系列新颖的2-羟基-12-芳基-8,9,10,12-四氢苯并[ a ]吨蒽-11-酮1,3-二羰基化合物，在乙醇和离子液体四氟硼酸咪唑鎓丁基甲基磺酸盐（[bmim] BF 4）中催化量的对甲苯磺酸存在下。新开发的方案操作简便，适用范围广，并且易于后处理，从而以高纯度提供了高纯度的多种取代的标题化合物。J.杂环化​​学。（2011）。
• Guanidine Hydrochloride: A Highly Efficient Organocatalyst for the Synthesis of 12-Aryl-8,9,10,12-tetrahydrobenzo[<i>a</i>]xanthene-11-ones Under Solvent-Free Conditions
  作者：Mahdieh Sadeghpour、Abolfazl Olyaei、Mortaza Rezaei

  DOI：10.1002/jhet.1879

  日期：2016.5

  A new green protocol has been developed for the synthesis of 12‐aryl‐8,9,10,12‐tetrahydrobenzo[a]xanthen‐11‐ones using guanidine hydrochloride as an organocatalyst under solvent‐free conditions. Operational simplicity, mild reaction conditions, enhanced rates, high isolated yields of the pure products, and purification of products by nonchromatographic methods are significant advantages of the protocol

  已开发出一种新的绿色方案，用于在无溶剂条件下使用盐酸胍作为有机催化剂合成12-芳基-8,9,10,12-四氢苯并[ a ]黄酮-11-酮。操作简便，温和的反应条件，提高的速率，纯产物的高分离产率以及通过非色谱法纯化产物是此处提出的方案的重要优点。