10-(4-methylphenyl)-9-(4-methoxyphenyl)-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-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: 10-(4-methylphenyl)-9-(4-methoxyphenyl)-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione
• 英文别名: 3,4,6,7-tetrahydro-9-(4-methoxyphenyl)-10-p-tolylacridine-1,8-(2H,5H,9H,10H)-dione；9-(4-methoxyphenyl)-10-(p-tolyl)-3,4,6,7,9,10-hexahydroacridine-1,8-[2H,5H]-dione；9-(4-methoxyphenyl)-10-(4-methylphenyl)-3,4,5,6,7,9-hexahydro-2H-acridine-1,8-dione
• 化学式: C₂₇H₂₇NO₃
• 分子量: 413.516
• InChiKey: VWFZMZAXBBLWMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-(4-methoxybenzylidene)-4-methylaniline 、 1,3-环己二酮 以 乙二醇 为溶剂， 反应 0.08h， 以90%的产率得到10-(4-methylphenyl)-9-(4-methoxyphenyl)-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione
  参考文献：
  名称：

  席夫碱与二甲酮的新反应：微波辐射下cr啶衍生物的新方法

  摘要：

  描述了席夫碱的新型级联反应。反应中提供的产物取决于两种原料的比例。提出了反应的可能机理，该机理经历了碳原子和氮原子之间的键的断裂和新形成。

  DOI：

  10.1002/jhet.5570440114

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。
• 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）。
• Proline-Catalyzed Simple and Efficient Synthesis of 1,8-Dioxo-decahydroacridines in Aqueous Ethanol Medium
  作者：K. Venkatesan、Suresh S. Pujari、Kumar V. Srinivasan

  DOI：10.1080/00397910802044306

  日期：2008.12.31

  Abstract Proline-catalyzed synthesis of 1,8-dioxo-decahydroacridines is achieved via one-pot, three-component condensation of aromatic aldehydes, cyclic diketone, and aryl amines in aqueous ethanol medium. This method offers the advantages of proceeding in neutral and mild conditions, giving high to excellent yields of acridines with easy workup procedure.

  摘要 通过芳香醛、环二酮和芳胺在乙醇水溶液中的一锅三组分缩合反应，脯氨酸催化合成 1,8-二氧代-十氢吖啶。该方法具有在中性和温和条件下进行的优点，可通过简单的后处理程序获得高至极好的吖啶收率。
• New reaction of schiff base with dimedone: New method for the acridine derivatives under microwave irradiation
  作者：Shujiang Tu、Tuanjie Li、Yan Zhang、Feng Shi、Jianing Xu、Qian Wang、Jinpeng Zhang、Xiaotong Zhu、Bo Jiang、Runhong Jia、Junyong Zhang

  DOI：10.1002/jhet.5570440114

  日期：2007.1

  A novel cascade reaction of Schiff's base was described. The products afforded in the reaction depended on the ratio of the two starting materials. A possible mechanism of the reactions is proposed, which underwent the breaking and new formation of the bond between carbon atom and nitrogen atom.

  描述了席夫碱的新型级联反应。反应中提供的产物取决于两种原料的比例。提出了反应的可能机理，该机理经历了碳原子和氮原子之间的键的断裂和新形成。