9-(2-hydroxyphenyl)-3,3,6,6-tetramethyl-10-phenyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione | 370873-62-4

• 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-(2-hydroxyphenyl)-3,3,6,6-tetramethyl-10-phenyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione
• 英文别名: 9-(2-hydroxyphenyl)-3,3,6,6-tetramethyl-10-phenyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione；9-(2-hydroxyphenyl)-3,3,6,6-tetramethyl-10-phenyl-4,5,7,9-tetrahydro-2H-acridine-1,8-dione
• CAS: 370873-62-4
• 化学式: C₂₉H₃₁NO₃
• 分子量: 441.57
• InChiKey: WWSWQJOGUQENNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  33
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  水杨醛 、 5,5-二甲基-1,3-环己二酮 、 苯胺 在 N-propyl benzoguanamine sulfonic acid-modified silica supported on magnetic Fe₃O₄ nanoparticles 作用下， 以 乙醇 、 水 为溶剂， 反应 0.33h， 以93%的产率得到9-(2-hydroxyphenyl)-3,3,6,6-tetramethyl-10-phenyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione
  参考文献：
  名称：

  磁性Fe 3 O 4纳米粒子上负载的N-丙基苯并胍胺磺酸：一种新颖高效的磁性非均相催化剂，用于合成1,8-二氧-十氢hydro啶衍生物†

  摘要：

  在这项研究中，根据绿色化学原理，制备了N-丙基-苯并胍胺-SO 3 H稳定的磁性纳米颗粒，作为一种新的非均相酸催化剂。新的催化剂用于在单级1,8-二氧代decahydroacridine的衍生物的合成通过芳香醛，和双甲酮乙酸铵或苯胺以高产率和短的反应时间之间的四部分冷凝反应。通过获得的纳米颗粒的结构傅里叶变换红外光谱（IR），场发射扫描电子显微镜（FE-SEM），透射电子显微镜（TEM），能量色散X射线分析（EDXA），X射线衍射（XRD），热重分析（TGA） ，振动样品磁力法（VSM），原子吸收光谱法（AAS）和电感耦合等离子体质谱法（ICP-MS）进行了评估。结果表明，合成的磁性纳米粒子的尺寸为约25nm。非均相催化剂可以容易地通过外部磁体回收，并且可以重复使用几次而不会显着降低催化活性。

  DOI：

  10.1039/c7nj03508j

文献信息

• <i>N</i>-Propyl benzoguanamine sulfonic acid supported on magnetic Fe₃O₄ nanoparticles: a novel and efficient magnetically heterogeneous catalyst for the synthesis of 1,8-dioxo-decahydroacridine derivatives
  作者：Masoumeh Gholami Dehbalaei、Naser Foroughifar、Hoda Pasdar、Alireza Khajeh-Amiri

  DOI：10.1039/c7nj03508j

  日期：——

  N-propyl-benzoguanamine-SO3H-stabilized magnetic nanoparticles were prepared as a new heterogeneous acid catalyst in accordance with the principles of green chemistry. The new catalyst is used for the synthesis of derivatives of 1,8-dioxo-decahydroacridine in one-stage via four-partial condensation reactions between aromatic aldehydes, dimedone and ammonium acetate or aniline with high yield and short reaction

  在这项研究中，根据绿色化学原理，制备了N-丙基-苯并胍胺-SO 3 H稳定的磁性纳米颗粒，作为一种新的非均相酸催化剂。新的催化剂用于在单级1,8-二氧代decahydroacridine的衍生物的合成通过芳香醛，和双甲酮乙酸铵或苯胺以高产率和短的反应时间之间的四部分冷凝反应。通过获得的纳米颗粒的结构傅里叶变换红外光谱（IR），场发射扫描电子显微镜（FE-SEM），透射电子显微镜（TEM），能量色散X射线分析（EDXA），X射线衍射（XRD），热重分析（TGA） ，振动样品磁力法（VSM），原子吸收光谱法（AAS）和电感耦合等离子体质谱法（ICP-MS）进行了评估。结果表明，合成的磁性纳米粒子的尺寸为约25nm。非均相催化剂可以容易地通过外部磁体回收，并且可以重复使用几次而不会显着降低催化活性。
• Amberlite IR-120H catalyzed MCR: Design, synthesis and crystal structure analysis of 1,8-dioxodecahydroacridines as potential inhibitors of sirtuins
  作者：Ali Nakhi、P.T.V.A. Srinivas、Md. Shafiqur Rahman、Ravada Kishore、G.P.K. Seerapu、K. Lalith Kumar、Devyani Haldar、M.V. Basaveswara Rao、Manojit Pal

  DOI：10.1016/j.bmcl.2013.01.026

  日期：2013.3

  A rapid, inexpensive and high yielding method has been developed for the synthesis of 1,8-dioxodecahydroacridines using Amberlite IR-120H as a reusable catalyst under open air. These compounds were designed as potential inhibitors of sirtuins and prepared via the MCR of 5,5-dimethyl-1,3-cyclohexanedione, (hetero)aryl aldehydes and (hetero)aromatic amines under mild conditions. Further structure elaboration of a representative compound was performed via Pd catalyzed C-C bond forming reactions. The crystal structure analysis and H-bonding patterns along with in vitro inhibitory activity against yeast Sir2 of the same compound is presented. Docking studies indicated that the compound interacts well with the yeast Sir2. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis and transformations of new 1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione derivatives
  作者：A. N. Pyrko

  DOI：10.1134/s1070428008080198

  日期：2008.8

  Reactions of cyclohexane-1,3-diones with amines and aldehydes led to the formation of 1,21,3,4,5,16,7,8,9, 10-decahydroacridine-1,8-diones containing alkylaryl, aryl, and hydroxy substituents in position 10. Transformations of 10-hydroxy-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-diones under oxidation with nitrous acid, reduction with zinc powder, as well as on heating in aprotic solvents and acetic, phosphoric, and polyphosphoric acids, were studied. NMR spectra of 1,2,3,4,5,6,7,8,9,10-decaliydroacridine-1,8-diones having different substituents in positions 9 and 10 were analyzed.
• Fe₃O₄@Sap/Cu(<scp>ii</scp>): an efficient magnetically recoverable green nanocatalyst for the preparation of acridine and quinazoline derivatives in aqueous media at room temperature
  作者：Milad Kazemnejadi、Mohammad Ali Nasseri、Safoora Sheikh、Zinat Rezazadeh、Seyyedeh Ameneh Alavi Gol

  DOI：10.1039/d1ra01373d

  日期：——

  Saponin, as a green and available phytochemical, was immobilized on the surface of magnetite nanoparticles then doped with Cu ions (Fe3O4@Sap/Cu(II)) and used as an efficient nanocatalyst for the synthesis of quinazoline and acridine derivatives, due to their high application and importance in various fields of science. Different spectroscopic and microscopic techniques were used for the catalyst characterization

  皂苷作为一种绿色、可用的植物化学物质，固定在磁铁矿纳米粒子表面，然后掺杂铜离子（Fe 3 O 4 @Sap/Cu( II )），作为有效的纳米催化剂用于合成喹唑啉和吖啶衍生物，由于它们在各个科学领域的高度应用和重要性。使用不同的光谱和显微技术来表征催化剂，例如 FT-IR、XRD、FE-SEM、EDX、TEM、TGA、VSM、BET、DLS、CV 和 XPS 分析。所有表征数据都相互关联，以便准确表征催化剂的结构。该反应在少量 Fe 3 O 4 @Sap/Cu( II ) (0.42 mol%) 作为绿色催化剂的存在下在水中在短时间内进行。结果很好地表明了皂苷在解决水介质中传质问题方面的有效作用，这是水介质中和非均相介质存在下许多有机反应所面临的挑战。该催化剂具有高催化活性，并且在温和的反应条件下，在短反应时间（小于 1 小时）内，所有喹唑啉（产率 68-94%）和吖啶（产率 66-97%