3-(1,2,3,4,5,6,7,8,9,10-decahydro-3,3,6,6-tetramethyl-1,8-dioxo-10-p-tolylacridin-9-yl)benzonitrile | 1228050-07-4

• 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-(1,2,3,4,5,6,7,8,9,10-decahydro-3,3,6,6-tetramethyl-1,8-dioxo-10-p-tolylacridin-9-yl)benzonitrile
• 英文别名: 3-(3,3,6,6-tetramethyl-1,8-dioxo-10-(p-tolyl)-1,2,3,4,5,6,7,8,9,10-decahydroacridin-9-yl)benzonitrile；3-(2,3,4,5,6,7,9,10-octahydro-3,3,6,6-tetramethyl-1,8-dioxo-10-(p-tolyl)acridin-9-yl)benzonitrile；3-[3,3,6,6-tetramethyl-10-(4-methylphenyl)-1,8-dioxo-4,5,7,9-tetrahydro-2H-acridin-9-yl]benzonitrile
• CAS: 1228050-07-4
• 化学式: C₃₁H₃₂N₂O₂
• 分子量: 464.607
• InChiKey: APJLOHWJIRERPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  35
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  61.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-氰基苯甲醛 、 乙烷,三氯氟- 、 5,5-二甲基-1,3-环己二酮 在 sulfuric acid-modified poly(vinylpyrrolidone) 作用下， 以 乙醇 、 水 为溶剂， 反应 0.5h， 以94%的产率得到3-(1,2,3,4,5,6,7,8,9,10-decahydro-3,3,6,6-tetramethyl-1,8-dioxo-10-p-tolylacridin-9-yl)benzonitrile
  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

• Synthesis of 1,8-Dioxo-decahydroacridine Derivatives <i>via</i> Ru-Catalyzed Acceptorless Dehydrogenative Multicomponent Reaction
  作者：Nandita Biswas、Dipankar Srimani

  DOI：10.1021/acs.joc.1c01075

  日期：2021.7.16

  A Ru-catalyzed acceptorless dehydrogenative multicomponent reaction has been developed. This reaction offers a cost-effective and simple operational strategy to synthesize biologically active 1,8-dioxodecahydroacridine derivatives. The protocol provides a wide range of substrate scope and various functional groups are also well tolerated under the reaction condition. To shed light on the mechanistic

  已经开发了 Ru 催化的无受体脱氢多组分反应。该反应为合成具有生物活性的 1,8-二氧十氢吖啶衍生物提供了一种经济高效且简单的操作策略。该协议提供了广泛的底物范围，并且在反应条件下也可以很好地耐受各种官能团。为了阐明机械和动力学研究，进行了一些对照实验和氘标记实验。还介绍了一个与时间相关的产品分布实验，并进行了反应放大以突出该策略的实际效用。
• 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.
• 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。