2-hydroxy-12-phenyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one | 1352090-43-7

• 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: 2-hydroxy-12-phenyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one
• CAS: 1352090-43-7
• 化学式: C₂₃H₁₈O₃
• 分子量: 342.394
• InChiKey: NZDTVRIXRLIIPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-hydroxy-12-phenyl-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84%的产率得到2-((1-(7-chloroquinolin-4-yl)-1H-1,2,3-triazol-4-yl)methoxy)-12-phenyl-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 、 1,3-环己二酮 、 苯甲醛 在 N-methyl-2-pyrrolidonium dihydrogenphosphate 作用下， 反应 0.67h， 以93%的产率得到2-hydroxy-12-phenyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one
  参考文献：
  名称：

  使用任务特定的酸性离子液体[NMP] H2PO4合成12-芳基-8,9,10,12-四氢苯并[a] x吨-11-酮衍生物的新绿色方法

  摘要：

  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。

  DOI：

  10.1016/j.cclet.2014.05.014

文献信息

• 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。
• 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）。
• 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。
• Efficient One Pot Synthesis of Xanthene-Triazole-Quinoline/Phenyl Conjugates and Evaluation of their Antimicrobial Activity
  作者：Harjinder Singh、Bhaskara Nand、Jayant Sindhu、Jitender M. Khurana、Chetan Sharma、Kamal R. Aneja

  DOI：10.5935/0103-5053.20140095

  日期：——

  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.