12-(2,3-dichlorophenyl)-9,9-dimethyl-9,10-dihydro-8H-benzo[a]xanthen-11(12H)-one | 1363402-19-0

• 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-(2,3-dichlorophenyl)-9,9-dimethyl-9,10-dihydro-8H-benzo[a]xanthen-11(12H)-one
• CAS: 1363402-19-0
• 化学式: C₂₅H₂₀Cl₂O₂
• 分子量: 423.339
• InChiKey: NSTMDOIESYCHBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.31
• 重原子数：
  29.0
• 可旋转键数：
  1.0
• 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：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  5,5-二甲基-1,3-环己二酮 、 2,3-二氯苯甲醛 、 2-萘酚 在 1-sulfopyridinium chloride 作用下， 以 neat (no solvent) 为溶剂， 反应 0.15h， 以95%的产率得到12-(2,3-dichlorophenyl)-9,9-dimethyl-9,10-dihydro-8H-benzo[a]xanthen-11(12H)-one
  参考文献：
  名称：

  离子液体磺酸官能化氯化吡啶鎓的制备，表征及应用为无溶剂合成12-芳基-8,9,10,12-四氢苯并[ a ]-黄原-11-酮的有效催化剂

  摘要：

  在这项工作中，合成了新型离子液体，即磺酸官能化的吡啶鎓氯化物{[吡啶-SO 3 H] Cl}，并通过研究其IR，UV，1 H和13 C NMR以及质谱进行了表征。这种离子液体可作为一种有效，均质且可重复使用的催化剂，用于通过一锅多组分无溶剂合成12-芳基-8,9,10,12-四氢苯并[ a ]-黄原-11-酮2-萘酚与芳醛和二甲酮（5,5-二甲基环己烷-1,3-二酮）的缩合反应。

  DOI：

  10.1016/j.molliq.2013.05.009

文献信息

• 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。
• Solvent-free Synthesis of 1,8-Dioxo-octahydroxanthenes and Tetra-hydrobenzo[a]xanthene-11-ones over Poly(<i>N,N</i>′-dibromo-<i>N</i>-ethylnaphtyl-2,7-sulfonamide)
  作者：Ardeshir Khazaei、Mahshid Rezaei、Ahmad Reza Moosavi-Zare、Shahnaz Saednia

  DOI：10.1002/jccs.201700082

  日期：2017.9

  In this work, poly(N,N′‐dibromo‐N‐ethylnaphtyl‐2,7‐sulfonamide) (PDNES) as a highly efficient catalyst was applied for the synthesis of 1,8‐dioxo‐octahydroxanthenes and tetra‐hydrobenzo[a]xanthene‐11‐ones under neutral and solvent‐free conditions.
• Application of silica-bonded imidazolium-sulfonic acid chloride (SBISAC) as a heterogeneous nanocatalyst for the domino condensation of arylaldehydes with 2-naphthol and dimedone
  作者：Ahmad Reza Moosavi-Zare、Mohammad Ali Zolfigol、Mahmoud Zarei、Abdolkarim Zare、Vahid Khakyzadeh

  DOI：10.1016/j.molliq.2015.07.049

  日期：2015.11

  In this work, a novel nanostructured silica-bonded ionic liquid namely silica-bonded imidazolium-sulfonic acid chloride (SBISAC) has been prepared, and characterized by Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), thermal gravimetric analysis (TGA), differential thermal gravimetric (DTG), transmission electron microscopy (TEM) and energy dispersive X-ray analysis (EDX) spectra. Then, SBISAC was utilized as an efficient and heterogeneous nanocatalyst for the synthesis of 12-aryl-8,9,10,12-tetrahydrobenzo[a]-xanthen-11-ones via the one-pot three-component condensation reaction of arylaldehydes with 2-naphthol and dimedone (5,5-dimethylcyclohexane-1,3-dione) under solvent-free conditions. (C) 2015 Elsevier B.V. All rights reserved.
• Organocatalyst trityl chloride efficiently promoted the solvent-free synthesis of 12-aryl-8,9,10,12-tetrahydrobenzo[a]-xanthen-11-ones by in situ formation of carbocationic system in neutral media
  作者：Ardeshir Khazaei、Mohammad Ali Zolfigol、Ahmad Reza Moosavi-Zare、Abdolkarim Zare、Mahmoud Khojasteh、Zhila Asgari、Vahid Khakyzadeh、Ali Khalafi-Nezhad

  DOI：10.1016/j.catcom.2012.01.001

  日期：2012.4

  A highly efficient and novel procedure for the preparation of 12-aryl-8,9,10,12-tetrahydrobenzo[a]-xanthen-11-one derivatives via the one-pot three-component condensation of 2-naphthol with arylaldehydes and dimedone in the presence of catalytic amount of trityl chloride (TrCl) as a homogeneous organocatalyst under natural and solvent-free conditions is described. It is interesting that TrCl by in situ formation of trityl carbocation with inherent instability catalyzes the reaction. (C) 2012 Elsevier B.V. All rights reserved.