12-(2-bromophenyl)-9,9-dimethyl-8,9,10,12-tetrahydro-11H-benzo[a]xanthen-11-one | 1011735-69-5

• 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-(2-bromophenyl)-9,9-dimethyl-8,9,10,12-tetrahydro-11H-benzo[a]xanthen-11-one
• 英文别名: 9,9-Dimethyl-12-(2-bromophenyl)-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one；12-(2-bromophenyl)-9,9-dimethyl-10,12-dihydro-8H-benzo[a]xanthen-11-one
• CAS: 1011735-69-5
• 化学式: C₂₅H₂₁BrO₂
• 分子量: 433.345
• InChiKey: JHHQXSNNRMSUPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  28
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  17-(2-Bromophenyl)-11-oxa-16-azatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,8-pentaene 在 dipotassium peroxodisulfate 、 copper(II) bis(trifluoromethanesulfonate) 、 silver nitrate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 5.5h， 生成 12-(2-bromophenyl)-9,9-dimethyl-8,9,10,12-tetrahydro-11H-benzo[a]xanthen-11-one
  参考文献：
  名称：

  解构环化介导的呫吨衍生物的一锅法合成

  摘要：

  通过解构环化方法在一锅操作下实现了萘嗪直接转化为各种呫吨衍生物。在有氧反应条件下进行连续氧化C(sp 3 )–O/C(sp 3 )–N裂解和分子内/分子间成环反应。对基材进行的机理分析表明，C(sp 3 )-O 键断裂取代了 C(sp 3 )-N 键断裂。通过C(sp 3 )–O裂解原位生成的Betti碱中间体被成功分离。基于分子对接研究，分子间环状产物表现出良好的α-葡萄糖苷酶抑制特性。

  DOI：

  10.1039/d4ob00093e

文献信息

• New nano-Fe₃O₄-supported Lewis acidic ionic liquid as a highly effective and recyclable catalyst for the preparation of benzoxanthenes and pyrroles under solvent-free sonication
  作者：Hai Truong Nguyen、Ngoc-Phuong Thi Le、Duy-Khiem Nguyen Chau、Phuong Hoang Tran

  DOI：10.1039/c8ra04893b

  日期：——

  magnetic nanomaterial-immobilized Lewis acidic ionic liquid was successfully synthesized by the covalent embedding of 3-(3-(trimethoxysilyl)propyl)-1H-imidazol-3-ium chlorozincate (II) ionic liquid to the surface of Fe3O4 nanoparticles. The material was then characterized by FT-IR, SEM, TEM, TGA, ICP-OES, Raman, and EDS. Its performance as a new-generation Lewis acidic catalyst was also examined on the

  将3-(3-(三甲氧基甲硅烷基)丙基)-1 H-咪唑-3-氯锌酸盐( II )离子液体共价嵌入Fe 3 O表面，成功合成了一种新型磁性纳米材料固定化Lewis酸性离子液体4纳米粒子。然后通过 FT-IR、SEM、TEM、TGA、ICP-OES、拉曼和 EDS 对材料进行表征。其作为新一代路易斯酸性催化剂的性能也在超声介导的苯并氧杂蒽和吡咯合成中进行了检验。完成后，通过外部磁铁简单地回收催化剂以进行多次重复使用，而不会显着降低催化性能。
• Polyvinylpolypyrrolidone supported triflic acid (PVPP.OTf); an efficient and recyclable heterogeneous catalyst for one-pot condensation of β-naphthol, aldehydes, and cyclic 1,3-dicarbonyl compounds
  作者：Satra Vahdat、Samad Khaksar

  DOI：10.1007/s11164-013-1521-5

  日期：2015.7

  Polyvinylpolypyrrolidoniume triflate (PVPP.OTf) is found to be a recyclable heterogeneous catalyst for the one-pot condensation of β-naphthol, aldehydes, and cyclic 1,3-dicarbonyl compounds in good to excellent yield under reflux conditions. These catalytic condensations have advantages from the viewpoint of green chemistry. PVPP.OTf catalyst is air-stable, cost-effective, easy to handle, easily separated

  聚乙烯吡咯烷酮三氟甲磺酸乙烯酯（PVPP.OTf）被发现是可回收的非均相催化剂，用于在回流条件下以良好的收率很好地合成β-萘酚，醛和环状1,3-二羰基化合物。从绿色化学的观点来看，这些催化缩合具有优点。PVPP.OTf催化剂是空气稳定的，具有成本效益的，易于处理的，易于与反应产物分离的，并且以极高的纯度回收后可直接重复使用。
• Preparation of various xanthene derivatives over sulfonic acid functionalized imidazolium salts (SAFIS) as novel, highly efficient and reusable catalysts
  作者：Mohammad Ali Zolfigol、Vahid Khakyzadeh、Ahmad Reza Moosavi-Zare、Abdolkarim Zare、Seyedeh Bahareh Azimi、Zhila Asgari、Alireza Hasaninejad

  DOI：10.1016/j.crci.2012.05.003

  日期：2012.8

  Abstract In this work, some novel sulfonic acid functionalized imidazolium salts (SAFIS), as a new category of ionic liquids, are synthesized by eco-friendly and simple procedures, and used as highly efficient and reusable catalysts to promote the following one-pot multicomponent organic transformations under solvent-free conditions: (i) the synthesis of 14-aryl-14H-dibenzo[a,j]xanthenes from β-naphthol

  摘要 在这项工作中，一些新型的磺酸功能化咪唑鎓盐（SAFIS）作为一种新型的离子液体，通过环保和简单的方法合成，并用作高效和可重复使用的催化剂，以促进以下一锅多组分无溶剂条件下的有机转化：(i) 从 β-萘酚 (2 eq.) 和芳醛 (1 eq.) 合成 14-芳基-14H-二苯并[a,j] 呫吨，(ii) 制备来自 β-萘酚、芳醛和二甲酮的四氢苯并 [a] 呫吨-11-酮，以及 (iii) 从二甲酮 (2 eq.) 和芳香醛 (1 eq.) 合成 1,8-二氧代-八氧杂蒽。环境友好、方法简单、后处理容易、反应清洁、反应时间短、收率高、催化剂易于制备是这项工作的一些优点。
• Nanocrystalline TiO2–HClO4 catalyzed three-component preparation of derivatives of 1-amidoalkyl-2-naphthol, 1-carbamato-alkyl-2-naphthol, 1-(α-aminoalkyl)-2-naphthol, and 12-aryl-8,9,10,12-tetrahydrobenzo[a]-xanthen-11-one
  作者：Hamid Reza Shaterian、Majid Mohammadnia

  DOI：10.1007/s11164-012-0938-6

  日期：2013.11

  1-Amidoalkyl-2-naphthols, 1-carbamatoalkyl-2-naphthols, and 1-(α-aminoalkyl)-2-naphthols have been prepared by three-component reaction of 2-naphthol, aromatic aldehydes, and NH compounds, i.e. amides, carbamates, and secondary amines, respectively, in the presence of a catalytic amount of nanocrystalline TiO2–HClO4. In addition, 12-aryl-8,9,10,12-tetrahydrobenzo[a]-xanthen-11-one derivatives have been synthesized by reaction of 2-naphthol, aromatic aldehydes, and dimedone in the presence of the same nano catalyst. These reactions were studied under solvent-free conditions. This white acidic heterogeneous catalyst is very stable under the reaction conditions and was reused several times without significant loss of activity.

  在催化剂纳米晶 TiO2-HClO4 的存在下，通过 2-萘酚、芳香醛和 NH 化合物（即酰胺、氨基甲酸酯和仲胺）的三组分反应，分别制备了 1-氨基烷基-2-萘酚、1-氨基甲酰基-2-萘酚和 1-(α-氨基烷基)-2-萘酚。此外，在相同的纳米催化剂存在下，通过 2-萘酚、芳香醛和二甲酮的反应，合成了 12-芳基-8,9,10,12-四氢苯并[a]-氧杂蒽-11-酮衍生物。这些反应是在无溶剂条件下进行研究的。这种白色酸性异相催化剂在反应条件下非常稳定，可重复使用多次，且活性无明显下降。
• Pentafluorophenylammonium Triflate (PFPAT): An Efficient, Practical, and Cost-Effective Catalyst for One-Pot Condensation of β-Naphthol, Aldehydes and Cyclic 1,3-Dicarbonyl Compounds
  作者：Samad Khaksar、Nosratollah Behzadi

  DOI：10.2174/138620712803901153

  日期：2012.11.7

  A pentafluorophenylammonium triflate (PFPAT) catalyst (10 mol%) efficiently promoted one-pot condensation of β-naphthol, aldehydes, and cyclic 1,3-dicarbonyl compounds in good to excellent yield under mild reaction conditions. These catalytic condensations have advantages from the viewpoint of green chemistry. PFPAT organocatalyst is air-stable, cost-effective, easy to handle, and easily removed from

  在轻度的反应条件下，五氟苯基三氟甲磺酸铵（PFPAT）催化剂（10 mol％）有效地促进了β-萘酚，醛和环状1,3-二羰基化合物的一锅缩合。从绿色化学的观点来看，这些催化缩合具有优点。PFPAT有机催化剂是空气稳定的，具有成本效益的，易于处理的，并且易于从反应混合物中除去。