3,3,6,6-tetramethyl-9,10-diphenyl-1,2,3,4,5,6,7,8,9,10-diphenyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione

• 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: 3,3,6,6-tetramethyl-9,10-diphenyl-1,2,3,4,5,6,7,8,9,10-diphenyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione
• 英文别名: 3,3,6,6‑tetramethyl‑9,10‑diphenyl‑1,8‑dioxodecahydroacridine；3,3,6,6-tetramethyl-1,8-dioxo-9-benzene-10-(4-phenyl)-1,2,3,4,5,6,7,8,9,10-decahydroacridine；3,3,6,6-tetramethyl-9-(phenyl)-10-phenyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione；9-phenyl-3,4,6,7-tetrahydro-3,3,6,6-tetramethyl-10-phenylacridine-1,8(2H,5H,9H,10H)-dione；3,3,6,6-tetramethyl-9,10-diphenyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione；3,3,6,6-tetramethyl-9,10-diphenyl-3,4,6,7,9,10-hexahydroacridine-1,8-(2H,5H)-dione；3,3,6,6-tetramethyl-9,10-diphenyl-4,5,7,9-tetrahydro-2H-acridine-1,8-dione
• 化学式: C₂₉H₃₁NO₂
• 分子量: 425.571
• InChiKey: BXNVVDLMFDVBIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  32
• 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：
  37.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯甲醛 在 溶剂黄146 、 L-脯氨酸 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 27.0h， 生成 3,3,6,6-tetramethyl-9,10-diphenyl-1,2,3,4,5,6,7,8,9,10-diphenyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione
  参考文献：
  名称：

  L-脯氨酸在室温下催化合成芳香醛和酮及其吖啶酮衍生物

  摘要：

  一系列呫吨衍生物是由环己烷-1,3-二酮和芳香醛通过 Knoevenagel-Michael 和在甲醇:乙醇混合物 (1:1) 中的环化反应制备的，在室温下由极少量的 l-脯氨酸催化。在相同条件下由二甲酮和芳香醛合成异构四酮。它们与胺缩合得到吖啶酮衍生物。获得并通过 X 射线单晶衍射确定吖啶酮的晶体结构。

  DOI：

  10.3184/174751915x14377428213215

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。
• A green and efficient procedure for one-pot synthesis of xanthenes and acridines using silica boron–sulfuric acid nanoparticles (SBSANs) as a solid Lewis-protic acid
  作者：Ali Khalafi-Nezhad、Farhad Panahi、Somayeh Mohammadi、Habib Ollah Foroughi

  DOI：10.1007/s13738-012-0140-1

  日期：2013.4

  Silica boron–sulfuric acid nanoparticles (SBSANs) as a solid Lewis-protic acid have been found to be an efficient heterogeneous catalyst in the synthesis of xanthene and acridine derivatives. The SBSAN-catalyzed reaction between carbonyl compound (aldehyde/ketone/ethyl orthoformate) and 5,5-dimethyl-1,3-cyclohexanedione (dimedone) for synthesis of xanthene derivatives is performed under mild conditions with the excellent isolated yield. Also, we can apply a broad scope of carbonyl compounds and amines for efficient synthesis of various acridine derivatives in the presence of SBSAN catalyst. In these multicomponent approaches the SBSAN catalyst can be reused for several times without any treatment in its catalytic activity.

  硅硼硫酸纳米颗粒（SBSANs）作为一种固态Lewis-质子酸，已被发现是合成氧杂蒽和吖啶衍生物的高效非均相催化剂。在温和条件下，通过SBSAN催化下的羰基化合物（醛/酮/原甲酸三乙酯）与5,5-二甲基-1,3-环己二酮（二甲基酮）的反应合成氧杂蒽衍生物，具有出色的分离产率。此外，我们可以在SBSAN催化剂的存在下，应用广泛的羰基化合物和胺，高效合成各种吖啶衍生物。在这些多组分方法中，SBSAN催化剂无需任何处理即可多次重复使用，其催化活性保持不变。
• Fe₃O₄@Sap/Cu(<scp>ii</scp>): an efficient magnetically recoverable green nanocatalyst for the preparation of acridine and quinazoline derivatives in aqueous media at room temperature
  作者：Milad Kazemnejadi、Mohammad Ali Nasseri、Safoora Sheikh、Zinat Rezazadeh、Seyyedeh Ameneh Alavi Gol

  DOI：10.1039/d1ra01373d

  日期：——

  Saponin, as a green and available phytochemical, was immobilized on the surface of magnetite nanoparticles then doped with Cu ions (Fe3O4@Sap/Cu(II)) and used as an efficient nanocatalyst for the synthesis of quinazoline and acridine derivatives, due to their high application and importance in various fields of science. Different spectroscopic and microscopic techniques were used for the catalyst characterization

  皂苷作为一种绿色、可用的植物化学物质，固定在磁铁矿纳米粒子表面，然后掺杂铜离子（Fe 3 O 4 @Sap/Cu( II )），作为有效的纳米催化剂用于合成喹唑啉和吖啶衍生物，由于它们在各个科学领域的高度应用和重要性。使用不同的光谱和显微技术来表征催化剂，例如 FT-IR、XRD、FE-SEM、EDX、TEM、TGA、VSM、BET、DLS、CV 和 XPS 分析。所有表征数据都相互关联，以便准确表征催化剂的结构。该反应在少量 Fe 3 O 4 @Sap/Cu( II ) (0.42 mol%) 作为绿色催化剂的存在下在水中在短时间内进行。结果很好地表明了皂苷在解决水介质中传质问题方面的有效作用，这是水介质中和非均相介质存在下许多有机反应所面临的挑战。该催化剂具有高催化活性，并且在温和的反应条件下，在短反应时间（小于 1 小时）内，所有喹唑啉（产率 68-94%）和吖啶（产率 66-97%
• 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。
• Zn^II doped and immobilized on functionalized magnetic hydrotalcite (Fe₃O₄/HT-SMTU-Zn^II): a novel, green and magnetically recyclable bifunctional nanocatalyst for the one-pot multi-component synthesis of acridinediones under solvent-free conditions
  作者：Z. Zarei、B. Akhlaghinia

  DOI：10.1039/c7nj03281a

  日期：——

  showed that the nanocatalyst has both acidic sites (site density: 22.66 mmol g−1) and basic sites (site density: 8.49 mmol g−1), and can act as a bifunctional nanocatalyst. The loading amount of ZnII (doped and immobilized) on functionalized magnetic hydrotalcite was indicated to be 4 mmol g−1, obtained from the ICP-OES analysis. The catalytic activity of this new magnetic nanocatalyst (Fe3O4/HT-SMTU-ZnII)

  Zn II掺杂并固定在功能化磁性水滑石（Fe 3 O 4 / HT-SMTU-Zn II）首次制备为稳定，长寿命，高效和优异的可重复使用磁性纳米催化剂，用于一键多组分合成cri啶二酮作为重要的杂环化合物。合成的催化剂通过各种光谱和显微技术进行表征，例如傅立叶变换红外（FT-IR）光谱，X射线衍射（XRD）分析，Brunauer，Emmett和Teller（BET）表面积分析，程序升温脱附（TPD） ，扫描电子显微镜（SEM），能量色散X射线光谱（EDX），透射电子显微镜（TEM），热重分析（TGA），振动样品磁强（VSM），电感耦合等离子体原子发射光谱（ICP-OES）和CHNS分析。表征结果表明，该催化剂具有超顺磁性，其平均粒径为20–60 nm，呈板状。另外，TPD分析的结果表明，纳米催化剂同时具有两个酸性位点（位点密度：22.66 mmol g-1）和碱性位点（位点密度：8.49 mmol