9-(4-methoxyphenyl)-10-phenyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione | 2176-31-0

• 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: 9-(4-methoxyphenyl)-10-phenyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione
• 英文别名: 9-(4-methoxyphenyl)-10-phenyl-3,4,6,7,9,10-hexahydro-2H,5H-acridine-1,8-dione；9-(4-Methoxyphenyl)-10-phenyl-3,4,6,7,9,10-hexahydro-1,8(2H,5H)-acridinedione；9-(4-methoxyphenyl)-10-phenyl-3,4,5,6,7,9-hexahydro-2H-acridine-1,8-dione
• CAS: 2176-31-0
• 化学式: C₂₆H₂₅NO₃
• 分子量: 399.489
• InChiKey: QUGPGSDNZKWXSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲醇 、 9-(4-methoxyphenyl)-10-phenyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione 在 iron(III) chloride 作用下， 生成 1,8-dimethoxy-9-(4-methoxyphenyl)-10-phenylacridin-10-ium chloride
  参考文献：
  名称：

  高效铁催化的无配体访问a啶和a啶离子

  摘要：

  就它们在药物，材料，染料和光催化中的用途而言，啶和a啶离子是重要的一类化合物。在这里，我们提出了一种非常规的FeCl 3-醇催化一锅法，用于直接从醛，1,3-环己二酮和胺进行合成。该方法有效地融合了高原子经济性和多组分反应的多样性与新型铁催化的脱氢反应，其中有氧氧为末端氧化剂，在酒精溶剂中生成水为唯一的副产物。已成功演示了该方法的简便扩展。

  DOI：

  10.1039/d0gc00617c
• 作为产物：
  描述：

  2,2'-((4-methoxyphenyl)methylene) dicyclohexane-1,3-dione 、 苯胺 以 溶剂黄146 为溶剂， 反应 3.0h， 生成 9-(4-methoxyphenyl)-10-phenyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione
  参考文献：
  名称：

  9-(4-Methoxyphenyl)-10-phenyl-3,4,6,7,9,10-hexahydro-1,8(2H,5H)-acridinedione

  摘要：

  In the title compound, C26H25NO3, the central ring adopts a distorted boat conformation and the outer rings adopt half-chair conformations. The molecule is stabilized by C-H...O-type hydrogen bonds.

  DOI：

  10.1107/s0108270197017009

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。
• Ionic liquid immobilized on Fe3O4 nanoparticles: a magnetically recyclable heterogeneous catalyst for one-pot three-component synthesis of 1,8-dioxodecahydroacridines
  作者：Heshmatollah Alinezhad、Mahmood Tajbakhsh、Neda Ghobadi

  DOI：10.1007/s11164-015-2003-8

  日期：2015.12

  A magnetically recoverable nanocatalyst based on 1-methylimidazolium hydrogen sulfate ionic liquid has been synthesized by reaction of 1-methylimidazole with 3-(trimethoxysilyl)propyl chloride group, leading to formation of 1-methyl-3-(triethoxysilyl)propyl imidazolium chloride ([pmim]Cl). The ionic liquid was anchored onto silica-coated magnetic Fe3O4 particles, and Cl− anion exchange by treatment with H2SO4 afforded the corresponding immobilized ionic liquid MNP-[pmim]HSO4. The synthesized catalyst was characterized by various techniques such as Fourier-transform infrared (FT-IR) spectroscopy, X-ray diffraction (XRD) analysis, scanning electron microscopy (SEM), transmission electron microscopy (TEM), (differential) thermogravimetry (TG/DTG), CHN analysis, and vibrating-sample magnetometry (VSM), revealing the superparamagnetic nature of the particles. From electron microscopy (SEM and TEM) studies it can be inferred that the particles were mostly spherical in shape with average size of 20 nm. The loading amount of ionic liquid supported on the magnetic particles was indicated to be 0.98 mmol/g by the results of elemental and thermogravimetric analyses (CHN and TG). The catalytic activity of the supported ionic liquid was examined in synthesis of 1,8-dioxodecahydroacridines by condensation reaction of cyclic diketones with aromatic aldehydes and ammonium acetate or primary amines under solvent-free conditions. The catalyst could be easily recovered by applying an external magnetic field and reused for at least nine runs without deterioration in catalytic activity.

  一种基于1-甲基咪唑硫酸氢盐离子液体的磁性可回收纳米催化剂已通过1-甲基咪唑与3-（三甲氧基硅基）丙基氯反应合成，导致形成1-甲基-3-（三乙氧基硅基）丙基咪唑氯（[pmim]Cl）。将该离子液体固定在涂有二氧化硅的磁性Fe3O4粒子上，并通过用H2SO4处理置换Cl−阴离子，得到了相应的固定化离子液体MNP-[pmim]HSO4。该合成的催化剂通过傅里叶变换红外（FT-IR）光谱、X射线衍射（XRD）分析、扫描电子显微镜（SEM）、透射电子显微镜（TEM）、（差示）热重分析（TG/DTG）、CHN元素分析和振动样品磁力计（VSM）等多种技术进行表征，显示了粒子的超顺磁性质。从电子显微镜（SEM和TEM）研究可以推断，粒子大多呈球形，平均尺寸为20 nm。根据元素和热重分析（CHN和TG）的结果，固定在磁性粒子上的离子液体的负载量为0.98 mmol/g。在无溶剂条件下，通过环状二酮与芳香醛和乙酸铵或伯胺的缩合反应，研究了该固定化离子液体的催化活性，用于合成1,8-二氧十氢吖啶。该催化剂可通过施加外部磁场轻松回收，并可重复使用至少九次而不会降低催化活性。
• A green procedure for the synthesis of 1,8-dioxodecahydroacridine derivatives under microwave irradiation in aqueous media without catalyst
  作者：Zi-Qiang Tang、Yan Chen、Chang-Ning Liu、Ke-Ying Cai、Shu-Jiang Tu

  DOI：10.1002/jhet.322

  日期：——

  A green procedure for the synthesis of 1,8‐dioxo‐decahydroacridine derivatives is developed under microwave irradiation without catalyst in water. This method provides several advantages such as excellent yields (86–96%), simple workup procedure, and environment friendliness. J. Heterocyclic Chem., (2010).

  在没有催化剂的情况下，在微波辐射下，开发了一种绿色合成1,8-二氧代-十氢hydro啶衍生物的绿色方法。该方法具有许多优点，例如，出众的收率（86–96％），简单的后处理程序和环境友好性。J.杂环化​​学。（2010）。
• Water mediated reactions: TiO₂and ZnO nanoparticle catalyzed multi component domino reaction in the synthesis of tetrahydroacridinediones, acridindiones, xanthenones and xanthenes
  作者：Ilangovan Pugazhenthi、Shaik Mohammed Ghouse、Fazlur-Rahman Nawaz Khan、Euh Duck Jeong、Jong Seong Bae、Jong-Pil Kim、Eun Hyuk Chung、Yadavalli Suneel Kumar、Changalraya Dasaradhan

  DOI：10.1039/c4ra13045f

  日期：——

  Tetrahydroacridine-1,8-(2H,5H,9H,10H)-diones4from 1,3-cyclohexanedione and/or dimedone 1,2-chloro-3-formylquinoline2and anilines3in water at 90 °C were obtained by domino reaction approach.

  用多米诺反应方法，在90°C的水中，通过1,3-环己二酮和/或二甲酮与1,2-氯代-3-甲酰喹啉和苯胺得到了1,8-二氢喹啉-1,8-(2H,5H,9H,10H)-二酮4。
• Ceric ammonium nitrate (CAN) catalyzed synthesis of N-substituted decahydroacridine-1,8-diones in PEG
  作者：Mazaahir Kidwai、Divya Bhatnagar

  DOI：10.1016/j.tetlet.2010.03.033

  日期：2010.5

  Polyethylene glycol (PEG) was found to be an inexpensive non-toxic and effective medium for the one-pot synthesis of N-substituted decahydroacridine-1,8-diones in the presence of ceric ammonium nitrate (CAN) as the catalyst in high yields. Also, the solvent system can be recovered and reused; making this protocol economically and potentially viable.

  聚乙二醇（PEG）被发现是用于一锅合成N的廉价的无毒且有效的介质-如以高收率催化剂取代decahydroacridine -1,8-二酮在硝酸铈铵（CAN）的存在下。而且，溶剂系统可以回收和再利用。使该协议在经济上和潜在的可行性。