9-(4-chlorophenyl)-3,4,6,7-tetrahydro-10-(3-hydroxyphenyl)-3,3,6,6-tetramethylacridine-1,8(2H,5H,9H,10H)-dione | 1228050-10-9

• 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: 9-(4-chlorophenyl)-3,4,6,7-tetrahydro-10-(3-hydroxyphenyl)-3,3,6,6-tetramethylacridine-1,8(2H,5H,9H,10H)-dione
• 英文别名: 9-(4-chlorophenyl)-2,3,4,5,6,7,9,10-octahydro-3,3,6,6-tetramethyl-10-(3-hydroxyphenyl)acridine-1,8-dione；9-(4-chlorophenyl)-10-(3-hydroxyphenyl)-3,3,6,6-tetramethyl-4,5,7,9-tetrahydro-2H-acridine-1,8-dione
• CAS: 1228050-10-9
• 化学式: C₂₉H₃₀ClNO₃
• 分子量: 476.015
• InChiKey: OYXFEOGNWVANKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  34
• 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：
  57.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-氯苯甲醛 、 5,5-二甲基-1,3-环己二酮 、 3-氨基苯酚 在 sulfuric acid-modified poly(vinylpyrrolidone) 作用下， 以 乙醇 、 水 为溶剂， 反应 0.67h， 以92%的产率得到9-(4-chlorophenyl)-3,4,6,7-tetrahydro-10-(3-hydroxyphenyl)-3,3,6,6-tetramethylacridine-1,8(2H,5H,9H,10H)-dione
  参考文献：
  名称：

  Sulfuric acid-modified poly(vinylpyrrolidone) ((PVP–SO₃H)HSO₄): a new highly efficient, bio-degradable and reusable polymeric catalyst for the synthesis of acridinedione derivatives

  摘要：

  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。

  DOI：

  10.1039/c4ra12219d

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。
• One-Pot Multi Component Synthesis of Xanthenediones and Acridinediones at Room Temperature
  作者：Hamid Reza Safaei、Abolfazl Eshghi Movahhed、Mansooreh Davoodi、Mohsen Shekouhy、Vahid Rahmanian、Maryam Safaei

  DOI：10.14233/ajchem.2013.13260

  日期：——

  A facile and efficient protocol for the synthesis of xanthenedione and acridinrdione derivatives has been developed via the one-pot condensation reaction between dimedone and aldehydes (for the synthesis of xanthenediones) and dimedone, aldehydes and primary amines (for the synthesis of acridinediones) in presence of the formic acid as solvent at room temperature. All the products were obtained in good to excellent yields and all reactions were completed in short times.

  在室温下，以甲酸为溶剂，通过二聚酮和醛类（用于合成呫吨二酮）以及二聚酮、醛类和伯胺（用于合成吖啶二酮）之间的一锅缩合反应，开发出了一种简便高效的合成呫吨二酮和吖啶二酮衍生物的方法。所有产物的收率都很高，甚至非常高，而且所有反应都在很短的时间内完成。
• 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.
• Synthesis of 1,8-Dioxo-Decahydroacridines using Pyridinium Hydrogen Sulfate Ionic Liquid as an Green, Efficient and Reusable Catalyst
  作者：Somaye Karimian、Hassan Tajik

  DOI：10.2174/1570178613666160104232735

  日期：2016.2.10

  amine (1 mmol), PHSIL (0.65 mmol), CH3CN (3 mL) at 80°C, a series of 1,8-dioxo-decahydroacridines were synthesized via the one-pot three component reaction between various aromatic aldehydes and amines with dimedone. The aromatic aldehydes containing electrondonating and electron-withdrawing groups afforded 1,8-dioxo-9-aryl-10-aryl-decahydroacridines with high yields within short reaction times in

  背景：在这项研究中，吡啶鎓硫酸氢盐离子液体（PHSIL）被用作绿色，高效且可重复使用的催化剂，用于合成1,8-二氧-十氢hydro啶。在该催化剂的存在下，使不同的伯胺和芳族醛与5，5-二甲基-1，3-环己二酮（二甲酮）反应，并以优异的产率和较短的反应时间获得相应的产物。该研究的两个重要优点是可以通过水萃取轻松从反应混合物中分离出离子液体，并且回收能力高达六倍。 方法：在吡啶鎓硫酸氢盐离子液体（PHSIL）催化剂和相应的1,8-二氧杂环己烷存在下，将不同的伯胺和芳族醛与5,5-二甲基-1,3-环己二酮（二甲酮）反应十氢ac啶衍生物以优异的产率和短的反应时间获得。 结果：在以下条件下建立了最佳条件：醛（1 mmol），胺（1 mmol），PHSIL（0.65 mmol），CH 3 CN（3 mL）在80°C下，得到了一系列1,8-二氧-十氢ac啶通过各种芳香醛和胺与二甲酮之间的一锅三组分反应合