10,10-dimethyl-7-(4-hydroxylphenyl)-7,9,10,11-tetrahydro-9H-benzo[c]acridine-8-one

• 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: 10,10-dimethyl-7-(4-hydroxylphenyl)-7,9,10,11-tetrahydro-9H-benzo[c]acridine-8-one
• 英文别名: 10,10-dimethyl-7-(4-hydroxyphenyl)-7,10,11,12-tetrahydrobenzo[c]acridin-8(9H)-one；10,10-dimethyl-7-(p-hydroxyphenyl)-7,10,11,12-tetrahydrobenzo[c]acridin-8(9H)-one；7-(4-hydroxyphenyl)-10,10-dimethyl-7,10,11,12-tetrahydrobenzo[c]acridin-8(9H)-one；3,3-dimethyl-9-(4-hydroxyphenyl)-1,2,3,4,9,10-hexahydrobenzo[c]acridine-1-one；7-(4-Hydroxyphenyl)-10,10-dimethyl-7,9,11,12-tetrahydronaphtho[1,2-b]quinolin-8-one
• 化学式: C₂₅H₂₃NO₂
• 分子量: 369.463
• InChiKey: KXFSYINGMYFMQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5,5-二甲基-1,3-环己二酮 、 4-(naphthalen-1-yliminomethyl)phenol 在 苄基三乙基氯化铵 作用下， 以 水 为溶剂， 反应 18.0h， 以92%的产率得到10,10-dimethyl-7-(4-hydroxylphenyl)-7,9,10,11-tetrahydro-9H-benzo[c]acridine-8-one
  参考文献：
  名称：

  一种简单清洁的合成聚氢ac啶和喹啉衍生物的程序：席夫碱与1,3-二羰基化合物在水性介质中的反应

  摘要：

  通过席夫碱与1的反应，可以很好地收率很好地完成苯并[ c ] ac啶，苯并[ a ] ac啶，吡啶并[2,3- c ] ac啶和苯并[ f ]喹啉衍生物的清洁，简单合成。TEBA催化的水性介质中的3-二羰基化合物。通过1 H NMR，IR和元素分析对结构进行表征，并通过X射线衍射研究证实。

  DOI：

  10.1016/j.tetlet.2005.08.091

文献信息

• NH₂SO₃H and H₆P₂W₁₈O₆₂ · 18H₂O-Catalyzed, Three-Component, One-Pot Synthesis of Benzo[<i>c</i>]acridine Derivatives
  作者：Majid M. Heravi、Hamideh Alinejhad、Fatemeh Derikvand、Hossein A. Oskooie、Bita Baghernejad、Fatemeh F. Bamoharram

  DOI：10.1080/00397911.2010.550704

  日期：2012.7.15

  Abstract We report here two simple methods for the synthesis of benzo[c]acridine derivatives from three-component, one-pot condensation of 1-naphthylamine, dimedone, and a variety of substituted aldehydes in the presence of a catalytic amount of NH2SO3H or H6P2W18O62 · 18H2O under solvent-free conditions at 120 °C or in refluxing ethanol. GRAPHICAL ABSTRACT

  摘要 我们在此报告了在催化量的 NH2SO3H 或 H6P2W18O62 存在下，由 1-萘胺、二甲酮和各种取代醛的三组分一锅缩合合成苯并 [c] 吖啶衍生物的两种简单方法。 · 18H2O 在 120 °C 或回流乙醇中的无溶剂条件下。图形概要
• TiO₂ Nanoparticles as an Efficient Catalyst for the One-pot Preparation of Tetrahydrobenzo[c]acridines in Aqueous Media
  作者：Shahrzad Abdolmohammadi、Mahdieh Mohammadnejad、Faezeh Shafaei

  DOI：10.5560/znb.2013-2323

  日期：2013.4.1

  A series of tetrahydrobenzo[c]acridinone derivatives have been prepared by a one-pot fourcomponent reaction of 1-naphthol, aromatic aldehydes, dimedone, and ammonium acetate in aqueous media using a catalytic amount of titanium dioxide nanoparticles (TiO₂ NPs). The advantages of this novel protocol include the excellent yields, operational simplicity, short reaction time, easy work-up, reusability of the catalyst and an environmentally friendly procedure.

  通过在水介质中使用一定量的二氧化钛纳米颗粒（TiO2 NPs）催化 1-萘酚、芳香醛、二甲基酮和乙酸铵进行四组分一锅反应，制备了一系列四氢苯并[c]吖啶酮衍生物。这种新方案的优点包括：产率高、操作简单、反应时间短、易于操作、催化剂可重复使用以及程序对环境友好。
• Microwave-induced synthesis and anti-microbial activities of 7,10,11,12-tetrahydrobenzo[c]acridin-8(9H)-one derivatives
  作者：Vetrivel Nadaraj、Senniappan Thamarai Selvi、Sellappan Mohan

  DOI：10.1016/j.ejmech.2008.07.004

  日期：2009.3

  Some new substituted tetrahydroacridin-8-ones and diverse derivatives were synthesized by uncatalysed multi-component reaction of dimedone or cyclohexan-1,3-dione, alpha-naphthylamine and various (o,p,m)-substituted benzaldehydes. The in vitro anti-microbial activities of the prepared compounds were evaluated against some bacteria and fungi strains. The results suggested that the products 2a-g and 4a-g exhibited good inhibitory effect against most of the tested organisms. Especially, 2f, 2g, 4f and 4g were shown to be most effective against Rhodotorula rubra and Aspergillus parasiticus and compounds 2a, 2c, 2g, 4f and 4g proved to be effective with MIC values in the range of 3.9-7.8 mu g/ml. (C) 2008 Elsevier Masson SAS. All rights reserved.
• Ultrasound-Promoted One-Pot Synthesis of 7-Aryl-7,10,11,12-tetrahydrobenzo[c]acridin-8(9H)-one Derivatives
  作者：Hongjun Zang、Yong Zhang、Yingming Mo、Bowen Cheng

  DOI：10.1080/00397911.2010.517610

  日期：2011.11.1

  A series of 7-aryl-7,10,11,12-tetrahydrobenzo[c]acridin-8(9H)-one derivatives were synthesized via the three-component coupling from aromatic aldehydes, 1-naphthylamine, and 5,5-dimethylcyclohexane-1,3-dione catalyzed by stannous chloride dihydrate (SnCl2 center dot 2H(2)O) under ultrasonic irradiation at room temperature. The products were isolated in good yields within short reaction times.
• An efficient ultrasound-promoted method for the one-pot synthesis of 7,10,11,12-tetrahydrobenzo[c]acridin-8(9H)-one derivatives
  作者：Hongjun Zang、Yong Zhang、Yaping Zang、Bo-Wen Cheng

  DOI：10.1016/j.ultsonch.2009.11.003

  日期：2010.3

  A new, efficient and general method for preparation of 7,10,11,12-tetrahydrobenzo[c]acridin-8(9H)-one derivatives using ultrasound irradiation is reported. Under ultrasound, the reaction time is short, the yields are high and the reaction conditions are mild. (c) 2009 Elsevier B.V. All rights reserved.