3,9-diphenyl-3,4-dihydroacridin-1(2H)-one | 31611-97-9

• 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: 3,9-diphenyl-3,4-dihydroacridin-1(2H)-one
• 英文别名: 3,9-diphenyl-3,4-dihydro-2H-acridin-1-one；3,9-diphenyl-3,4-dihydro-2H-acridin-1-one
• CAS: 31611-97-9
• 化学式: C₂₅H₁₉NO
• 分子量: 349.432
• InChiKey: MVMMLSZOHDXGPS-UHFFFAOYSA-N

物化性质

• 沸点：
  554.9±50.0 °C(Predicted)
• 密度：
  1.206±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-phenyl-cyclohexane-1,3-dione 、 2-氨基二苯甲酮 在 indium(III) triflate 作用下， 以 neat (no solvent) 为溶剂， 反应 0.5h， 以78%的产率得到3,9-diphenyl-3,4-dihydroacridin-1(2H)-one
  参考文献：
  名称：

  弗里德兰德（Friedländer）环空反应：金属盐路易斯酸催化剂在选择性控制功能化喹啉合成中的范围和局限性

  摘要：

  检查了金属盐路易斯酸催化剂的范围和局限性，以控制在涉及2-氨基二苯甲酮和乙酰乙酸乙酯的反应过程中弗里德兰德和非​​弗里德兰德产品形成的选择性。在用作催化剂的一系列金属卤化物，四氟硼酸盐，高氯酸盐和三氟甲磺酸盐中，In（OTf）3成为选择性/排他地形成弗里德兰德产品的最有效催化剂。In（OTf）3催化的Friedländer反应的普遍性通过不同取代的2-氨基芳基酮与各种含有活性亚甲基的羰基化合物（例如，，无溶剂条件下的β-酮酸酯，环状/无环β-二酮，环状/酰基酮和芳基/杂芳基甲基酮），以75-92％的收率提供所需的喹啉。

  DOI：

  10.1039/c5nj02010g

文献信息

• Friedländer annulation: scope and limitations of metal salt Lewis acid catalysts in selectivity control for the synthesis of functionalised quinolines
  作者：Babita Tanwar、Dinesh Kumar、Asim Kumar、Md. Imam Ansari、Mohammad Mohsin Qadri、Maulikkumar D. Vaja、Madhulika Singh、Asit K. Chakraborti

  DOI：10.1039/c5nj02010g

  日期：——

  products during the reaction involving 2-aminobenzophenone and ethyl acetoacetate. Among a pool of metal halides, tetrafluoroborates, perchlorates, and triflates used as catalysts, In(OTf)3 emerged as the most effective catalyst for the selective/exclusive formation of the Friedländer product. The generality of the In(OTf)3-catalysed Friedländer reaction was demonstrated by the reaction of differently substituted

  检查了金属盐路易斯酸催化剂的范围和局限性，以控制在涉及2-氨基二苯甲酮和乙酰乙酸乙酯的反应过程中弗里德兰德和非​​弗里德兰德产品形成的选择性。在用作催化剂的一系列金属卤化物，四氟硼酸盐，高氯酸盐和三氟甲磺酸盐中，In（OTf）3成为选择性/排他地形成弗里德兰德产品的最有效催化剂。In（OTf）3催化的Friedländer反应的普遍性通过不同取代的2-氨基芳基酮与各种含有活性亚甲基的羰基化合物（例如，，无溶剂条件下的β-酮酸酯，环状/无环β-二酮，环状/酰基酮和芳基/杂芳基甲基酮），以75-92％的收率提供所需的喹啉。
• Design, development of new synthetic methodology, and biological evaluation of substituted quinolines as new anti-tubercular leads
  作者：Babita Tanwar、Asim Kumar、Perumal Yogeeswari、Dharmarajan Sriram、Asit K. Chakraborti

  DOI：10.1016/j.bmcl.2016.10.082

  日期：2016.12

  Two series of quinoline-based compounds were designed, synthesised and evaluated for anti-tubercular activity against Mycobacterium tuberculosis H(37)Rv (ATCC 27294 strain). A new method for Friedlander quinoline synthesis has been developed in water under the catalytic influence of the Bronsted acid surfactant DBSA. Among the forty-two compounds tested for anti-TB activity, twenty-three compounds exhibited significant activity against the growth of M. tuberculosis (MIC 0.02-6.25 mu g/mL). In particular, the compounds 3b and 3c displayed excellent anti-TB activity with MIC values of 0.2 and 0.39 mu g/mL, respectively, and are more potent than the standard drugs E, Cfx and Z that are clinically used to treat TB. The cytotoxicity of the compounds with MIC <= 6.25 mu g/mL was evaluated against Human Embryonic Kidney 293T cell lines and all of the active compounds were found to be nontoxic (<50% inhibition). The results suggest that the synthesised substituted quinolines are promising leads for development of new drug to treat TB. (C) 2016 Elsevier Ltd. All rights reserved.