10-(4-methylphenyl)-9-(4-nitrophenyl)-3,3,6,6-tetramethyl-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-nitrophenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione
• 英文别名: 3,3,6,6-tetramethyl-10-(4-methylphenyl)-9-(4-nitrophenyl)-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione；3,3,6,6-tetramethyl-9-(4-nitrophenyl)-10-(p-tolyl)-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione；9-(4-nitrophenyl)-10-(4-tolyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydroacridine-1,8-[2H,5H]-dione；3,3,6,6-tetramethyl-10-(4-methylphenyl)-9-(4-nitrophenyl)-4,5,7,9-tetrahydro-2H-acridine-1,8-dione
• 化学式: C₃₀H₃₂N₂O₄
• 分子量: 484.595
• InChiKey: DRDXFGPMBDGVAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  36
• 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：
  83.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-(4-nitrobenzylidene)-4-methylaniline 、 5,5-二甲基-1,3-环己二酮 以 乙二醇 为溶剂， 反应 0.07h， 以92%的产率得到10-(4-methylphenyl)-9-(4-nitrophenyl)-3,3,6,6-tetramethyl-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

• 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）。
• Fe3O4 nanoparticles: As an efficient, green and magnetically reusable catalyst for the one-pot synthesis of 1,8-dioxo-decahydroacridine derivatives under solvent-free conditions
  作者：Mohammad Ali Ghasemzadeh、Javad Safaei-Ghomi、Halimeh Molaei

  DOI：10.1016/j.crci.2012.08.010

  日期：2012.11

  Résumé An efficient and environmentally friendly method for the one-pot synthesis of 1,8-dioxo-decahydroacridines has been developed in the presence of Fe3O4 nanoparticles. The multicomponent reactions of aldehydes, dimedone and amines were carried out under solvent-free conditions to obtain some 1,8-dioxo-9-aryl-10-aryl-decahydroacridine derivatives. The present approach provides several advantages including high yields, short reaction times, little catalyst loading and facile catalyst separation.

  摘要：在Fe3O4纳米颗粒的存在下，开发了一种高效且环保的一锅法合成1,8-二氧代-十氢吖啶的方法。醛、二美克酮和胺的多组分反应在无溶剂条件下进行，以获得一些1,8-二氧代-9-芳基-10-芳基-十氢吖啶衍生物。该方法具有多种优点，包括高产率、短反应时间、催化剂用量少以及催化剂分离简便。
• Immobilization of organofunctionalized silica (SiMPTMS) with biphenyl-2,2′-dioic acid and investigation of its catalytic property for one-pot tandem synthesis of acridine-1,8-dione derivatives
  作者：Rupali Vaid、Monika Gupta、Vivek K. Gupta

  DOI：10.1007/s13738-017-1156-3

  日期：2017.10

  3-cyclohexanedione with various aldehydes. This method results in the synthesis of high-yielding acridine-1,8-dione derivatives and also provides simple and facile recyclability of the catalyst. The synthesized derivatives were characterized by IR, 1H-NMR, 13C-NMR and mass spectroscopy. Molecular structures of three acridine-1,8-dione derivatives were determined by single-crystal X-ray diffraction which determines

  摘要通过FTIR，TGA，TEM和SEM等多种光谱技术，合成并固定了MPTMS-官能化的固定有联苯-2,2'-二酸的二氧化硅。已经证明了合成催化剂对芳族胺和5，5-二甲基-1，3-环己二酮与各种醛的一锅法Knoevenagel / Michael缩合反应。该方法导致高产率的a啶-1，8-二酮衍生物的合成，并且还提供了催化剂的简单和容易的再循环性。合成的衍生物经IR，1 H-NMR，13表征。13 C-NMR和质谱。通过单晶X射线衍射确定三种three啶-1,8-二酮衍生物的分子结构，该晶体确定3,3,6,6-四甲基-9,10-二苯基-1,8-二氧代十二烷基氢化ca啶在单斜晶中结晶。具有空间组P2 1 / c的3,3,6,6-四甲基-9-（4-氯苯基）-10-（4-甲基苯基）-1,8-二氧十二烷基氢化hydro啶在具有空间组P2 1 / n的单斜晶体中结晶3,3,6,6-四甲基-9-（4-氯苯基）-10-（4-甲氧基苯基）-1
• One-Pot Synthesis of 1,8-Dioxodecahydroacridines using Ag-TiO₂ Nanocomposite as a Mild and Heterogeneous Catalytic System
  作者：Seyed Mohammad Vahdat、Ali Akbar Masoudi、Samad Khaksar

  DOI：10.2174/1570178619666220127122008

  日期：2022.11

  Ag-TiO2 nanocomposite is reported to be an efficient, active, and benign recyclable catalyst for highly efficient synthesis of 1,8-dioxodecahydroacridine derivatives from dimedone, aromatic aldehydes, and several anilines or ammonium acetate in ethanol as a solvent at room temperature in a short reaction time and suitable yield. This catalyst is effortlessly recycled by simple filtration and can be reused up to five times with only a negligible loss in its catalytic effectiveness. Low catalyst loading, cost-effectively mild conditions, non-chromatographic purification of target compounds, excellent atom economy, informal procedure, use of a cheaply accessible nanocomposite catalyst, and recyclability of the catalyst are all significant benefits of this method. AFM analysis is performed to confirm the structure, topography, and morphology of Ag-TiO2 nanocomposite. 1,8-dioxodecahydroacridine derivatives having natural significance possess a wide range of pharmacological activities; for instance, antibacterial, antimalarial, anticancer, and mutagenic properties. In terms of the distinctions between aldehydes and anilines, this approach offers a wide range of applications.

  摘要：报道了Ag-TiO2纳米复合材料作为高效、活性、无害可回收催化剂，用于在乙醇溶剂下室温下从二甲酮、芳香醛和若干苯胺或醋酸铵合成1,8-二氧杂十环癸烷衍生物的高效合成。该催化剂可通过简单的过滤轻松回收，并可重复使用多达五次，其催化效率仅有微不足道的损失。该方法具有低催化剂负载量、成本效益温和的条件、非色谱纯化目标化合物、优秀的原子经济性、简便的操作、使用成本低廉的纳米复合催化剂以及催化剂可回收性等显著优点。使用AFM分析证实了Ag-TiO2纳米复合材料的结构、拓扑和形态。具有天然重要性的1,8-二氧杂十环癸烷衍生物具有广泛的药理活性，例如抗菌、抗疟疾、抗癌和致突变性等。在醛和苯胺之间的区别方面，该方法提供了广泛的应用。
• 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。