3,4,6,7-tetrahydro-10-(2-hydroxyphenyl)-3,3,6,6-tetramethyl-9-(4-nitrophenyl)acridine-1,8(2H,5H,9H,10H)-dione | 1228050-11-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3,4,6,7-tetrahydro-10-(2-hydroxyphenyl)-3,3,6,6-tetramethyl-9-(4-nitrophenyl)acridine-1,8(2H,5H,9H,10H)-dione
• 英文别名: 2,3,4,5,6,7,9,10-octahydro-10-(2-hydroxyphenyl)-3,3,6,6-tetramethyl-9-(4-nitrophenyl)acridine-1,8-dione；10-(2-hydroxyphenyl)-3,3,6,6-tetramethyl-9-(4-nitrophenyl)-4,5,7,9-tetrahydro-2H-acridine-1,8-dione
• CAS: 1228050-11-0
• 化学式: C₂₉H₃₀N₂O₅
• 分子量: 486.568
• InChiKey: VODQTZPPDCGICS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  36
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  对硝基苯甲醛 、 5,5-二甲基-1,3-环己二酮 、 2-氨基苯酚 在 ferric(III) complex supported on silica coated superparamagnetite iron oxide nanoparticles Fe₃O₄(at)SiO₂ coated by mixture of 3,4-dihydroxybenzaldehyde, barbituric acid, phthalhydrazide 作用下， 以 neat (no solvent) 为溶剂， 反应 0.67h， 以92%的产率得到3,4,6,7-tetrahydro-10-(2-hydroxyphenyl)-3,3,6,6-tetramethyl-9-(4-nitrophenyl)acridine-1,8(2H,5H,9H,10H)-dione
  参考文献：
  名称：

  超顺磁性Fe 3 O 4 @SiO 2上负载的铁（III）络合物作为可重复使用的路易斯酸催化剂：a啶二酮和螺喹唑啉-4（3 H）-一衍生物的新型高效合成方法

  摘要：

  制备纳米Fe 3 O 4 @SiO 2 -3，4-二羟基苯甲醛/巴比妥酸/邻苯二甲酰-FeCl 3（纳米Fe 3 O 4 @SiO 2 -HBP-FeCl 3），并通过常规分析和光谱技术鉴定。将制备的纳米Fe 3 O 4 @SiO 2 -HBP-FeCl 3应用于a啶二酮和螺喹唑啉-4（3 H）-绿色条件下的一种衍生物。此外，这项研究还提供了许多优势，例如非常容易的反应条件，简单的后处理，优异的收率，所需产物的高纯度，较短的反应时间和一锅法反应以合成Fe 3 O 4 @SiO 2 -HBP- FeCl 3。回收研究表明，使用外磁体可以轻松回收催化剂，并重复使用五次，而不会明显降低其催化活性。

  DOI：

  10.1007/s11164-019-03942-w

文献信息

• Sulfuric acid-modified poly(vinylpyrrolidone) ((PVP–SO₃H)HSO₄): a new highly efficient, bio-degradable and reusable polymeric catalyst for the synthesis of acridinedione derivatives
  作者：Hamid Reza Safaei、Maryam Safaei、Mohsen Shekouhy

  DOI：10.1039/c4ra12219d

  日期：——

  The synthesis of a new biodegradable polymer catalyst and its efficiency for the synthesis of acridindiones.

  合成一种新的可生物降解聚合物催化剂及其在合成吖啶二酮中的效率。
• Silica-bonded<i>S</i>-sulfonic acid as recyclable catalyst for the synthesis of 1,8-dioxo-decahydroacridines and 1,8-dioxo-octahydroxanthenes
  作者：Khodabakhsh Niknam、Farhad Panahi、Dariush Saberi、Molki Mohagheghnejad

  DOI：10.1002/jhet.303

  日期：——

  Abstract magnified image Silica‐bonded S‐sulfonic acid (SBSSA) has been found to be an efficient catalyst for the synthesis of 1,8‐dioxo‐decahydroacridines and 1,8‐dioxo‐octahydroxanthenes in excellent yields. The former have been synthesized from aromatic aldehydes, amines, and 5,5‐dimethyl‐1,3‐cyclohexanedione, whereas the latter from this mixture without amines. The method is an easy access to functionalized acridine and xanthene derivatives. The catalyst can be reused. J. Heterocyclic Chem., (2010).
• Sulfonated Polyethylene Glycol (PEG-SO₃H) as Eco-Friendly and Potent Water Soluble Solid Acid for Facile and Green Synthesis of 1,8-Dioxo-Octahydroxanthene and 1,8-Dioxo-Decahydroacridine Derivatives
  作者：Alireza Hasaninejad、Mohsen Shekouhy、Marzieh Miar、Somayeh Firoozi

  DOI：10.1080/15533174.2014.900799

  日期：2016.1.2

  In this work, a green, simple, and highly efficient procedure for the preparation of 1,8-dioxo-octahydroxanthene and 1,8-dioxo-decahydroacridine derivatives (as biologically active heterocycles, fluorescence materials and Pharmaceutical compounds) is described. Sulfonated polyethylene glycol (PEG-SO3H) has been used as an efficient and reusable catalyst for the one-pot multi component domino condensation reaction of dimedone and an aromatic aldehyde without/and a primary amine. The reactions were completed at 80 degrees C in water as green solvent. Using this procedure, all the products were obtained in good to excellent yields. The catalyst has been recovered and reused several times without any lose of reactivity.
• Ferric (III) complex supported on superparamagnetic Fe3O4@SiO2 as a reusable Lewis acid catalyst: a new highly efficient protocol for the synthesis of acridinedione and spiroquinazolin-4(3H)-one derivatives
  作者：Hadi Mohammadi、Hamid Reza Shaterian

  DOI：10.1007/s11164-019-03942-w

  日期：2020.1

  very easy reaction conditions, simple work-up, excellent yields, high purity of the desired product, short reaction time and one-pot reaction to synthesize Fe3O4@SiO2-HBP-FeCl3. The recycling studies revealed that catalyst could be easily recovered using an external magnet and reused five times without significant loss of its catalytic activity.

  制备纳米Fe 3 O 4 @SiO 2 -3，4-二羟基苯甲醛/巴比妥酸/邻苯二甲酰-FeCl 3（纳米Fe 3 O 4 @SiO 2 -HBP-FeCl 3），并通过常规分析和光谱技术鉴定。将制备的纳米Fe 3 O 4 @SiO 2 -HBP-FeCl 3应用于a啶二酮和螺喹唑啉-4（3 H）-绿色条件下的一种衍生物。此外，这项研究还提供了许多优势，例如非常容易的反应条件，简单的后处理，优异的收率，所需产物的高纯度，较短的反应时间和一锅法反应以合成Fe 3 O 4 @SiO 2 -HBP- FeCl 3。回收研究表明，使用外磁体可以轻松回收催化剂，并重复使用五次，而不会明显降低其催化活性。