3,3,6,6-tetramethyl-9,10-di(4-methoxyphenyl)-3,4,6,7,9,10-hexahydro-2H,5H-acridine-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-di(4-methoxyphenyl)-3,4,6,7,9,10-hexahydro-2H,5H-acridine-1,8-dione
• 英文别名: 3,3,6,6-tetramethyl-9,10-bis(4-methoxyphenyl)-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione；9,10-bis(4-methoxyphenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione；3,3,6,6-tetramethyl-1,8-dioxo-9-(4-methoxyphenyl)-10-(4-methoxyphenyl)-1,2,3,4,5,6,7,8,9,10-decahydroacridine；3,3,6,6-Tetramethyl-9,10-di(4-methoxy-phenyl)-3,4,6,7,9,10-hexahydro-2h,5h-acridine-1,8-dione；9,10-bis(4-methoxyphenyl)-3,3,6,6-tetramethyl-4,5,7,9-tetrahydro-2H-acridine-1,8-dione
• 化学式: C₃₁H₃₅NO₄
• 分子量: 485.623
• InChiKey: GZWSTDSAHUWLKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  36
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-甲氧基苯甲醛 、 5,5-二甲基-1,3-环己二酮 、 甲氧苯胺 在 1-丁基-3-甲基咪唑溴盐 作用下， 反应 2.0h， 以99%的产率得到3,3,6,6-tetramethyl-9,10-di(4-methoxyphenyl)-3,4,6,7,9,10-hexahydro-2H,5H-acridine-1,8-dione
  参考文献：
  名称：

  醛，胺和二甲酮在离子液体中的三组分反应有效合成多氢ac啶衍生物

  摘要：

  本文制备了3,3,6,6-四甲基-9,10-二芳基-1,2,3,4,5,6,7,8,9,10-十氢ac啶-1,8-二酮衍生物描述了由醛，芳族胺和5，5-二甲基-1，3-环己二酮在1-正丁基-3-甲基咪唑鎓溴化物（[bmim] Br）中的组成。这些化合物的结构通过元素分析，IR和1 H NMR光谱进行表征，并通过单晶X射线衍射分析进一步证实。

  DOI：

  10.1002/jhet.5570450303

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。
• Acetic acid as an efficient catalyst for synthesis of 1,8-dioxo-octahydroxanthenes and 1,8-dioxo-decahydroacridines
  作者：Nourallah Hazeri、Amin Masoumnia、Malek Taher Mghsoodlou、Sajjad Salahi、Mehrnoosh Kangani、Samira Kianpour、Shiva Kiaee、Jasem Abonajmi

  DOI：10.1007/s11164-013-1516-2

  日期：2015.7

  1,8-Dioxo-octahydroxanthenes have been synthesized in good yields by reaction of arylaldehydes and dimedone in the presence of a catalytic amount of acetic acid, without use of any additional co-catalyst, under solvent-free, thermal conditions. We also report preparation of 1,8-dioxo-decahydroacridines by reaction of arylaldehydes, dimedone, and amines or ammonium acetate under solvent-free, thermal

  在无溶剂的热条件下，在催化量的乙酸存在下，不使用任何其他助催化剂的情况下，通过芳基醛与二甲酮的反应，可以高收率合成1,8-二氧-八氧杂蒽。我们还报告了在相同的催化剂存在下，在无溶剂的热条件下，通过芳基醛，二甲酮和胺或乙酸铵的反应制备1,8-二氧-十氢hydro啶。
• Saccharose as a new, natural, and highly efficient catalyst for the one-pot synthesis of 4,5-dihydropyrano[3,2-c]chromenes, 2-amino-3-cyano-4H-chromenes, 1,8-dioxodecahydroacridine, and 2-substituted benzimidazole derivatives
  作者：Malek Taher Maghsoodlou、Nourallah Hazeri、Mojtaba Lashkari、Fereshteh Nejad Shahrokhabadi、Behzad Naghshbandi、Mohammad Saeed Kazemi-doost、Mahnaz Rashidi、Fatemeh Mir、Mehrnoosh Kangani、Sajjad Salahi

  DOI：10.1007/s11164-014-1793-4

  日期：2015.10

  Saccharose was applied as a green and natural catalyst for the one-pot, three-component condensation between aromatic aldehydes, malononitrile, and resorcinol, or 4-hydroxycoumarine to afford the corresponding pyran-annulated heterocyclic systems. This green methodology offers several advantages such as the use of a non-hazardous catalyst, easy access, clean work-up, excellent yields, short reaction time, and environmentally mild conditions. In addition, 1,8-dioxodecahydroacridine and 2-substituted benzimidazole derivatives have been synthesized from commercially available starting materials, arylaldehydes, dimedone, amines, or ammonium acetate and o-phenylenediamine using the mentioned catalyst.

  蔗糖被用作绿色和天然催化剂，进行芳香醛、马来腈和儿茶酚或4-羟基香豆素之间的一锅三组分缩合反应，生成相应的吡喃缩合杂环体系。这种绿色方法具有多个优点，如使用无害催化剂、易于获得、清洁的后处理、优良的产率、短的反应时间以及环保的温和条件。此外，1,8-二氧代十氢吡啶和2-取代苯并咪唑衍生物是通过上述催化剂从商业可获得的起始材料（芳香醛、二酮、胺或醋酸铵和邻苯二胺）合成的。
• Green and expeditious synthesis of 1,8-dioxodecahydroacridine derivatives catalysed by protic pyridinium ionic liquid
  作者：HESHMATOLLAH ALINEZHAD、MAHMOOD TAJBAKHSH、MOHAMMAD NOROUZI、SAEED BAGHERY、JAMSHID RAKHTSHAH

  DOI：10.1007/s12039-013-0517-4

  日期：2013.11

  The Hantzsch three-component condensation reaction of various aromatic aldehydes, 1,3-dione and aniline derivatives in the presence of 2-methylpyridinium trifluoromethanesulphonate ([2-MPyH]OTf) as green and highly efficient catalysts in water affords 1,8-dioxodecahydroacridine derivatives in good to excellent yields. This reaction has been carried out in the presence of 1 mol% of [2-MPyH]OTf at room

  在3-甲基吡啶三氟甲烷磺酸酯（[2-MPyH] OTf）存在下，各种芳香族醛，1,3-二酮和苯胺衍生物的汉茨三组分缩合反应作为绿色高效的水溶液，可提供1,8-二氧杂双氢hydro啶衍生品，收益率极高。该反应在室温下在1mol％的[2-MPyH] OTf存在下进行。与传统的合成方法相比，所描述的新颖的合成方法具有条件温和，反应时间短，产率高，简单且易于后处理的多个优点。 使用[2-MPyH] OTf作为离子液体催化剂，以良好至极佳的收率合成了1,8-二氧十二烷基氢化hydro啶衍生物。