10,10-dimethyl-7-(2-hydroxyphenyl)-7,10,11,12-tetrahydrobenzo[c]acridin-8(9H)-one | 1146978-69-9

• 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: 10,10-dimethyl-7-(2-hydroxyphenyl)-7,10,11,12-tetrahydrobenzo[c]acridin-8(9H)-one
• 英文别名: 10,10-dimethyl-7-(o-hydroxyphenyl)-7,10,11,12-tetrahydrobenzo[c]acridin-8(9H)-one；7,10,11,12-Tetrahydro-7-(2-hydroxyphenyl)-10,10-dimethylbenz[c]acridin-8(9H)-one；7-(2-hydroxyphenyl)-10,10-dimethyl-7,9,11,12-tetrahydronaphtho[1,2-b]quinolin-8-one
• CAS: 1146978-69-9
• 化学式: C₂₅H₂₃NO₂
• 分子量: 369.463
• InChiKey: YTIBYEHSAXMVNX-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：

  1-萘胺 、 水杨醛 、 5,5-二甲基-1,3-环己二酮 在 L-脯氨酸 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以92%的产率得到10,10-dimethyl-7-(2-hydroxyphenyl)-7,10,11,12-tetrahydrobenzo[c]acridin-8(9H)-one
  参考文献：
  名称：

  l-Proline-catalysed one-pot synthesis of tetrahydrobenzo[c]acridin-8(7H)-ones at room temperature

  摘要：

  事实证明，乙醇中只有 10 摩尔的 l-脯氨酸是一种非常有效的催化剂，可在室温下一次合成多种高取代的四氢苯并[c]吖啶-8(7H)-酮。该工艺的主要优点是产率高、催化剂成本低、易于操作，而且产品可直接从热乙醇中重结晶。

  DOI：

  10.1016/j.crci.2011.12.001

文献信息

• γ-Fe₂O₃@Si-(CH₂)₃@mel@(CH₂)₄SO₃H as a magnetically bifunctional and retrievable nanocatalyst for green synthesis of benzo[c]acridine-8(9<i>H</i>)-ones and 2-amino-4<i>H</i>-chromenes
  作者：Fatemeh Karimirad、Farahnaz Kargar Behbahani

  DOI：10.1080/24701556.2020.1802751

  日期：2021.5.4

  analyses. In addition, the catalytic activity of this new catalyst was investigated for the synthesis of 7,10,11,12-tetrahydrobenzo[c]acridine-8(9H)-ones from aliphatic and aromatic aldehydes, dimedone and 1-naphthylamine in excellent yields and 2-amino-4H-chromenes were provided using manufactured nanocatalyst in good-to-high yield under mild reaction condition. The γ-Fe2O3@Si-(CH2)3@melamine@butyl sulfonic

  摘要 目前的工作描述了合成，并与支撑在磁性纳米粒子，γ -铁磺酸官能化的三聚氰胺的表征2 ö 3 @ SI-（CH 2）3 @三聚氰胺@丁基磺酸纳米颗粒作为绿色和检索双功能催化剂。通过FT-IR，XRD，EDX，TEM，VSM，CHN和TGA分析指定该催化剂。此外，还研究了这种新型催化剂的催化活性，该催化剂可在极好的条件下由脂肪族和芳香族醛，二甲酮和1-萘胺合成7,10,11,12-四氢苯并[c] -8啶-8（9 H）-酮。产量和2-氨基-4 H在温和的反应条件下，使用制得的纳米催化剂以高到高的产率提供二甲基苯酚。所述γ-的Fe 2 ö 3 @ SI-（CH 2）3 @三聚氰胺@丁基磺酸的非均相催化剂显示出的优点，如非常简单和生态友好的由于来自磁性纳米颗粒使用作为催化剂的高的可重用性，磁性可分离催化剂，收率高，反应条件温和。还报道了在这种纳米催化剂的存在下合成一些新的二苯并[ c ] r啶和2-氨基-4H-色烯衍生物。
• 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.
• l-Proline-catalysed one-pot synthesis of tetrahydrobenzo[c]acridin-8(7H)-ones at room temperature
  作者：Mohammad Reza Poor Heravi、Parinaz Aghamohammadi

  DOI：10.1016/j.crci.2011.12.001

  日期：2012.5

  Résumé Only 10 mol% of l-Proline in ethanol proved to be a very efficient catalyst for the one-pot synthesis of a wide variety of highly substituted tetrahydrobenzo[c]acridin-8(7H)-ones at room temperature. The key advantages of this process are high yields, cost effectiveness of the catalyst, easy work-up and the products can be directly recrystallized from hot ethanol.

  事实证明，乙醇中只有 10 摩尔的 l-脯氨酸是一种非常有效的催化剂，可在室温下一次合成多种高取代的四氢苯并[c]吖啶-8(7H)-酮。该工艺的主要优点是产率高、催化剂成本低、易于操作，而且产品可直接从热乙醇中重结晶。