2-(tert-butyl)-7-chloro-9-phenyl-1,2,3,4-tetrahydroacridine | 1093163-99-5

• 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: 2-(tert-butyl)-7-chloro-9-phenyl-1,2,3,4-tetrahydroacridine
• 英文别名: 2-Tert-butyl-7-chloro-9-phenyl-1,2,3,4-tetrahydroacridine
• CAS: 1093163-99-5
• 化学式: C₂₃H₂₄ClN
• 分子量: 349.903
• InChiKey: XPKLNSUXUAKDJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-氨基-5-氯二苯甲酮 、 4-叔丁基环己酮 在 (Bu₄N)₂S₂O₈ 作用下， 以 neat (no solvent) 为溶剂， 反应 1.0h， 以87%的产率得到2-(tert-butyl)-7-chloro-9-phenyl-1,2,3,4-tetrahydroacridine
  参考文献：
  名称：

  无溶剂条件下邻氨基芳酮与α-亚甲基酮的一锅杂环化反应合成取代喹啉的简便有效方法

  摘要：

  摘要 通过使用四丁基过二硫酸铵作为通用试剂（25 mol%），通过邻氨基芳基酮与多种 α-亚甲基酮的串联杂环化反应，开发了一种简便实用的合成多种功能化喹啉的方法。无溶剂条件下的环境温度。该方案应用于类药分子的合成，类药分子是生物碱喜树碱的关键中间体。图形概要

  DOI：

  10.1080/00397911.2016.1242746

文献信息

• Sulfuric acid-modified PEG-6000 (PEG-OSO3H): an efficient, bio-degradable and reusable polymeric catalyst for the solvent-free synthesis of poly-substituted quinolines under microwave irradiation
  作者：Alireza Hasaninejad、Abdolkarim Zare、Mohsen Shekouhy、Javad Ameri-Rad

  DOI：10.1039/c0gc00953a

  日期：——

  acid-modified polyethylene glycol 6000 (PEG-OSO3H) is applied as an efficient and eco-friendly polymeric catalyst for Friedländer synthesis of poly-substituted quinolines from 2-aminoaryl ketones (or anthranilonitrile) and carbonyl compounds possessing a reactive methylene group under microwave irradiation and solvent-free conditions. The reactions are completed in short times, and the products are obtained

  硫酸改性聚乙二醇6000（PEG-OSO 3 H）被用作一种高效且环保的聚合物催化剂 Friedländer合成多取代基 喹啉 由2-氨基芳基 酮类 （或者 蒽腈） 和 羰基化合物 在微波辐射下具有反应性亚甲基 溶剂无条件。反应在短时间内完成，并且以良好至优异的产率获得产物。
• Environmentally Friendly Nafion-Mediated Friedländer Quinoline Synthesis under Microwave Irradiation: Application to One-Pot Synthesis of Substituted Quinolinyl Chalcones
  作者：Cheng-Chung Wang、Chieh-Kai Chan、Chien-Yu Lai

  DOI：10.1055/s-0039-1690088

  日期：2020.6

  An efficient and eco-friendly synthetic route for Friedländer quinoline synthesis of polysubstituted quinolines is described. This green chemical method starts from various 2-aminobenzophenones and mono- or dicarbonyl synthons and uses reusable Nafion NR50 material as a solid catalyst in ethanol under microwave irradiation. The protocol has a high generality of functional groups and provides the desired

  描述了一种用于弗里德兰德喹啉合成多取代喹啉的有效而环保的合成途径。这种绿色化学方法从各种2-氨基二苯甲酮和单或二羰基合成子开始，并在微波辐射下使用可重复使用的Nafion NR50材料作为乙醇中的固体催化剂。该方案具有很高的官能团通用性，并以良好或优异的产率提供了所需的喹啉。通过单晶X射线衍射分析确认了一些结构。
• Synthesis and Application of Double Perovskite Bi1.97Eu0.03MoO6 as Heterogeneous and Recyclable Nanocatalyst for Quinoline Synthesis
  作者：Tejeswararao Dharmana、B. Nagamani Naidu

  DOI：10.14233/ajchem.2022.23428

  日期：——

  An efficient and economical protocol for the synthesis of substituted quinolines from various 2-amino aryl ketones and aliphatic ketones in presence of a catalytic quantity of double perovskite Bi1.97Eu0.03MoO6 catalyst, water at ambient temperature to generate the respective quinolines in good yields. The accompanied catalyst had high activity and stability and it might be utilized at least a few times without losing its effectiveness.

  一种高效经济的合成取代喹啉的方法，通过在存在双钙钛矿Bi1.97Eu0.03MoO6催化剂的情况下，使用少量水和各种2-氨基芳基酮和脂肪酮合成相应的喹啉，反应在常温下进行，产率较高。所用的催化剂具有高活性和稳定性，可以至少使用几次而不会失去效果。
• Diversity-Oriented Synthesis of Quinolines via Friedländer Annulation Reaction under Mild Catalytic Conditions
  作者：D. Subhas Bose、Mohd. Idrees、N. M. Jakka、J. Venkateswara Rao

  DOI：10.1021/cc900129t

  日期：2010.1.11

  An efficient and practical method has been manifested for the diversity-oriented synthesis of quinolines via Friedlander annulation reaction for the generation of a wide range of structurally interesting and pharmacologically significant compounds by using ceric ammonium nitrate as a catalyst (10 mol %) at ambient temperature in 45 min. A variety of functional groups are introduced at various positions of the quinoline moiety, and further the diversity of the core skeleton was expanded at R-1 and R-2 positions by the synthesis of various hybrids. Initial screening of the compounds for cytotoxicity against a series of cancer cell lines showed promising results,
• 1-Butyl-3-methylimidazolium Hydrogen Sulfate ([bmim]-HSO₄)–Mediated Synthesis of Polysubstituted Quinolines
  作者：Hassan Tajik、Khodabakhsh Niknam、Marjan Sarrafan

  DOI：10.1080/00397911.2010.497596

  日期：2011.7.15

  [image omitted] In this research, polysubstituted quinolines are prepared from the reaction of 2-aminobenzophenones and ethylacetoacetate or ketones in the presence of 1-butyl-3-methylimidazolium hydrogen sulfate [bmim]HSO4 as an acidic ionic liquid in good to high yields at 70 degrees C under solvent-free conditions.