3,3,6,6-tetramethyl-9-(2,4-dimethoxyphenyl)-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione | 333433-32-2

• 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-(2,4-dimethoxyphenyl)-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione
• 英文别名: 9-(2',4'-dimethoxyphenyl)-3,3,6,6-tetramethyl-2,4,5,7,9,10-hexahydroacridine-1,8-dione；9-(2,4-dimethoxyphenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione；9-(2,4-dimethoxyphenyl)-3,3,6,6-tetramethyl-2,4,5,7,9,10-hexahydroacridine-1,8-dione
• CAS: 333433-32-2
• 化学式: C₂₅H₃₁NO₄
• 分子量: 409.525
• InChiKey: XTTZVVZPRCUVQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5,5-二甲基-1,3-环己二酮 、 2,4-二甲氧基苯甲醛 在 γ-maghemite 、 ammonium acetate 作用下， 以 neat (no solvent) 为溶剂， 反应 0.1h， 以91%的产率得到3,3,6,6-tetramethyl-9-(2,4-dimethoxyphenyl)-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione
  参考文献：
  名称：

  Magnetically Separable Recyclable Nano-ferrite Catalyst for the Synthesis of Acridinediones and Their Derivatives under Solvent-free Conditions

  摘要：

  纳米铁氧体在温和条件下合成吖啶二酮及其衍生物的催化活性得到了探讨；在无溶剂反应中，报告了一种更环保的方案，具有优异的产率和可回收性，无需使用任何添加剂或助催化剂。纳米铁氧体催化剂采用溶胶-凝胶法在低温下合成。X射线衍射（XRD）和透射电子显微镜（TEM）结果显示，具有立方相的磁铁矿（γ-Fe2O3）平均粒径为18纳米。此外，该催化剂可以通过外部磁铁轻松分离，并在九个循环内重复使用，活性几乎没有显著损失。

  DOI：

  10.1246/cl.150503

文献信息

• An efficient synthesis of polyhydroacridine derivatives by the three-component reaction of aldehydes, amines and dimedone in ionic liquid
  作者：Da-Qing Shi、Sai-Nan Ni、Fang-Yang、Jing-Wen Shi、Guo-Lan Dou、Xiao-Yue Li、Xiang-Shan Wang

  DOI：10.1002/jhet.5570450303

  日期：2008.5

  In this paper the preparation of 3,3,6,6-tetramethyl-9,10-diaryl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione derivatives from aldehydes, aromatic amines and 5,5-dimethyl-1,3-cyclohexanedione in 1-n-butyl-3-methylimidazolium bromide ([bmim]Br) is described. The structures of these compounds were characterized by elemental analysis, IR and 1H NMR spectra and further confirmed by single crystal X-ray

  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。
• Magnetically Separable Recyclable Nano-ferrite Catalyst for the Synthesis of Acridinediones and Their Derivatives under Solvent-free Conditions
  作者：Palla Mahesh、Kolakaluri Guruswamy、Bhagavathula Subrahmanya Diwakar、Bhoomireddy Rama Devi、Yellajyosula Lakshmi Narasimha Murthy、Pratap Kollu、Sri Venkata Narayan Pammi

  DOI：10.1246/cl.150503

  日期：2015.10.5

  Catalytic activity of nano-ferrite is explored in the synthesis of acridinedione and their derivatives under benign conditions; a greener protocol is reported in terms of excellent yield and recyclability under solvent-free reactions without using any additive/cocatalyst. Nano-ferrite catalyst is synthesized using sol–gel process at low temperatures. X-ray diffraction (XRD) and transmission electron microscopy (TEM) results exhibit cubic phase of maghemite (γ-Fe2O3) with average particle size of 18 nm. Furthermore, the catalyst can be easily separated using an external magnet and reused up to nine cycles without any significant loss of activity.

  纳米铁氧体在温和条件下合成吖啶二酮及其衍生物的催化活性得到了探讨；在无溶剂反应中，报告了一种更环保的方案，具有优异的产率和可回收性，无需使用任何添加剂或助催化剂。纳米铁氧体催化剂采用溶胶-凝胶法在低温下合成。X射线衍射（XRD）和透射电子显微镜（TEM）结果显示，具有立方相的磁铁矿（γ-Fe2O3）平均粒径为18纳米。此外，该催化剂可以通过外部磁铁轻松分离，并在九个循环内重复使用，活性几乎没有显著损失。
• Study on one-pot four-component synthesis of 9-aryl-hexahydro-acridine-1,8-diones using SiO2–I as a new heterogeneous catalyst and their anticancer activity
  作者：K.B. Ramesh、M.A. Pasha

  DOI：10.1016/j.bmcl.2014.06.047

  日期：2014.8

  A simple, efficient and cost-effective method for the synthesis of 9-aryl-hexahydro-acridine-1,8-diones by a one-pot four-component cyclocondensation of dimedone, aromatic aldehydes and ammonium acetate as a nitrogen source in the presence of a new heterogeneous catalyst silica iodide (SiO2-I) in EtOH at 80 °C is described. SiO2-I was subjected to SEM-EDX and found to have iodo group bound to the catalyst. Some of the prepared acridine-diones were found to exhibit promising anti-cancer activity against HepG2 and MCF-7 cell lines.
• Nano-TiO₂as an Efficient Catalyst for Tandem Knoevenagel-Michael-Cyclocondensation Reaction of Dimedone with Aromatic Aldehydes and Ammonium Acetate or Aromatic Amines under Solvent-free Conditions
  作者：Ardeshir Khazaei、Ahmad Reza Moosavi-Zare、Zahra Mohammadi、Vahid Khakyzadeh、Javad Afsar

  DOI：10.1002/jccs.201500384

  日期：2016.2

  and successfully applied as an efficient and heterogeneous catalyst in the synthesis of 1,8‐dioxo‐decahydroacridines via the one‐pot multi‐component condensation reaction of dimedone with aromatic aldehydes and ammonium acetate or aromatic amines under mild and solvent‐free conditions.

  通过X射线衍射（XRD），扫描电子显微镜（SEM），透射电子显微镜（TEM）等多种技术对锐钛矿型和金红石型TiO 2纳米颗粒进行了表征和研究，并成功地将其用作高效，多相催化剂。在温和且无溶剂的条件下，通过二甲酮与芳族醛和乙酸铵或芳族胺的单锅多组分缩合反应得到1,8-二氧代十氢hydro啶。