9-(3'-cyanophenyl)-3,3,6,6-tetramethyl-2,4,5,7,9,10-hexahydro-acridine-1,8-dione | 1387578-31-5

• 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-(3'-cyanophenyl)-3,3,6,6-tetramethyl-2,4,5,7,9,10-hexahydro-acridine-1,8-dione
• 英文别名: 9-(3'-cyanophenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione；3-(3,3,6,6-tetramethyl-1,8-dioxo-1,2,3,4,5,6,7,8,9,10-decahydroacridin-9-yl)benzonitrile；3-(3,3,6,6-Tetramethyl-1,8-dioxo-2,4,5,7,9,10-hexahydroacridin-9-yl)benzonitrile；3-(3,3,6,6-tetramethyl-1,8-dioxo-2,4,5,7,9,10-hexahydroacridin-9-yl)benzonitrile
• CAS: 1387578-31-5
• 化学式: C₂₄H₂₆N₂O₂
• 分子量: 374.483
• InChiKey: FTNMFMMHXHGBFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  70
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-羟甲基苯甲腈 、 5,5-二甲基-1,3-环己二酮 在 potassium tert-butylate 、 C₃₇H₃₇Cl₂NPRuS₂ 、 尿素 作用下， 反应 36.0h， 以52%的产率得到9-(3'-cyanophenyl)-3,3,6,6-tetramethyl-2,4,5,7,9,10-hexahydro-acridine-1,8-dione
  参考文献：
  名称：

  的1,8-二氧代decahydroacridine衍生物的合成经由钌催化的脱氢Acceptorless多组分反应

  摘要：

  已经开发了 Ru 催化的无受体脱氢多组分反应。该反应为合成具有生物活性的 1,8-二氧十氢吖啶衍生物提供了一种经济高效且简单的操作策略。该协议提供了广泛的底物范围，并且在反应条件下也可以很好地耐受各种官能团。为了阐明机械和动力学研究，进行了一些对照实验和氘标记实验。还介绍了一个与时间相关的产品分布实验，并进行了反应放大以突出该策略的实际效用。

  DOI：

  10.1021/acs.joc.1c01075

文献信息

• Acridinedione as selective flouride ion chemosensor: a detailed spectroscopic and quantum mechanical investigation
  作者：Nafees Iqbal、Syed Abid Ali、Iqra Munir、Saima Khan、Khurshid Ayub、Mariya al-Rashida、Muhammad Islam、Zahid Shafiq、Ralf Ludwig、Abdul Hameed

  DOI：10.1039/c7ra11974g

  日期：——

  to be highly selective chemosensors for fluoride ions only. To investigate in detail the mechanism of selective fluoride ion sensing, detailed spectroscopic studies were carried out using UV-visible, fluorescence and 1H NMR spectroscopy. Fluoride mediated (NH) proton abstraction of acridinedione was found to be responsible for the observed selective fluoride ion sensing. Quantum mechanical computational

  使用小分子作为离子检测化学传感器凭借其相对于传统离子传感方法的优势而迅速普及。在此，我们合成了一系列吖啶(1,8)二酮( 7a–7l )，并探索了它们作为化学传感器检测各种阴离子的潜力，例如氟离子 (F - )、乙酸根 (OAc - )、溴离子(Br - )、碘化物(I - )、硫酸氢盐(HSO 4 - )、氯酸盐(ClO 3 - )、高氯酸盐(ClO 4 - )、氰化物(CN - )和硫氰酸盐(SCN - )。吖啶二酮被发现是仅对氟离子具有高度选择性的化学传感器。为了详细研究选择性氟离子传感的机制，使用紫外-可见光、荧光和1 H NMR 光谱进行了详细的光谱研究。发现氟化物介导的 (NH) 吖啶二酮质子提取是观察到的选择性氟离子传感的原因。还使用时间相关密度泛函理论（TDDFT）进行了量子力学计算研究，比较吖啶二酮与氟离子和乙酸根离子的相互作用，解释了吖啶二酮检测氟阴离子的选择性。我们的
• 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.
• Synthesis of 1,8-Dioxo-decahydroacridine Derivatives <i>via</i> Ru-Catalyzed Acceptorless Dehydrogenative Multicomponent Reaction
  作者：Nandita Biswas、Dipankar Srimani

  DOI：10.1021/acs.joc.1c01075

  日期：2021.7.16

  A Ru-catalyzed acceptorless dehydrogenative multicomponent reaction has been developed. This reaction offers a cost-effective and simple operational strategy to synthesize biologically active 1,8-dioxodecahydroacridine derivatives. The protocol provides a wide range of substrate scope and various functional groups are also well tolerated under the reaction condition. To shed light on the mechanistic

  已经开发了 Ru 催化的无受体脱氢多组分反应。该反应为合成具有生物活性的 1,8-二氧十氢吖啶衍生物提供了一种经济高效且简单的操作策略。该协议提供了广泛的底物范围，并且在反应条件下也可以很好地耐受各种官能团。为了阐明机械和动力学研究，进行了一些对照实验和氘标记实验。还介绍了一个与时间相关的产品分布实验，并进行了反应放大以突出该策略的实际效用。