9-(4-chlorophenyl)-3,4,6,7-tetrahydro-3,3,6,6-tetramethyl-10-p-tolylacridine-1,8(2H,5H,9H,10H)-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: 9-(4-chlorophenyl)-3,4,6,7-tetrahydro-3,3,6,6-tetramethyl-10-p-tolylacridine-1,8(2H,5H,9H,10H)-dione
• 英文别名: 9-(4-chlorophenyl)-10-(4-methylphenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione；9-(4-Chlorophenyl)-3,3,6,6-tetramethyl-10-(4-methylphenyl)-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione；9-(4-chlorophenyl)-3,3,6,6-tetramethyl-10-(4-methylphenyl)-4,5,7,9-tetrahydro-2H-acridine-1,8-dione
• 化学式: C₃₀H₃₂ClNO₂
• 分子量: 474.043
• InChiKey: DCOWGQSTQYZTOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  34
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  2-{(4-chlorophenyl)[4,4-dimethyl-2-(4-methylanilino)-6-oxocyclohex-1-enyl]methyl}-3-hydroxy-5,5-dimethylcyclohex-2-enone 在 [1-butyl-3-methylimidazolium⁽¹⁺⁾][BF₄^(1-)] 作用下， 反应 1.0h， 以98%的产率得到9-(4-chlorophenyl)-3,4,6,7-tetrahydro-3,3,6,6-tetramethyl-10-p-tolylacridine-1,8(2H,5H,9H,10H)-dione
  参考文献：
  名称：

  3-苯胺基-5,5-二甲基环己-2-烯酮、苯甲醛和1,3-二羰基化合物在离子液体介质中的改进和良性合成9,10-二芳基吖啶-1,8-二酮和茚并喹啉衍生物

  摘要：

  9,10-二芳基吖啶-1,8-二酮和茚并喹啉衍生物的改进和绿色合成是通过3-苯胺基-5,5-二甲基环己-2-烯酮、苯甲醛和1,3-二羰基化合物的反应完成的。离子液体介质[bmim + ][BF 4 - ]。不仅含有给电子基团的取代苯胺，而且含有吸电子基团的苯胺均具有优异的产率。此外，获得了有趣的不对称 9,10-diarylacridine-1,8-dione 部分，在 3 位和 6 位具有不同的基团和茚并喹啉衍生物，并在文献中首次报道。成功获得了Knoevenagel缩合和迈克尔加成中间体。详细讨论了该反应的可能机理。

  DOI：

  10.1055/s-2006-950365

文献信息

• 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。
• p-Sulfonic acid calix[4]arene as an efficient and reusable catalyst for the synthesis of acridinediones and xanthenes
  作者：Seyed Meysam Baghbanian、Gonja Khanzad、Seyed Mohammad Vahdat、Hamed Tashakkorian

  DOI：10.1007/s11164-015-2001-x

  日期：2015.12

  p-Sulfonic acid calix[4]arene has been found to be an efficient catalyst for the synthesis of acridinediones and xanthenes under mild conditions in excellent yields. The present approach offers the advantages of simple methodology, short reaction time, and high yield.

  p-磺酸基杯[4]芳烃已被发现是一种高效的催化剂，能够在温和条件下合成吖啶二酮和咕吨类化合物，并具有极佳的产率。目前的方法具有简单的方法、短的反应时间和高产率的优点。
• 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。
• 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）。