9-(3-bromophenyl)-3,3,6,6-tetramethyl-3,4,6,7-tetrahydroacridine-1,8(2H,5H,9H,10H)-dione | 330472-22-5

• 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-bromophenyl)-3,3,6,6-tetramethyl-3,4,6,7-tetrahydroacridine-1,8(2H,5H,9H,10H)-dione
• 英文别名: 9-(3-bromophenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydro-(2H,5H)-acridine-1,8-dione；9-(3-bromophenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydroacridine-1,8 (2H,5H)-dione；9-(3-bromophenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H, 5H)-dione；3,3,6,6-tetramethyl-9-(3-bromophenyl)-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione；9-(3-bromophenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione；9-(3-bromophenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydroacridine-1,8-dione；9-(3-bromophenyl)-3,3,6,6-tetramethyl-2,4,5,7,9,10-hexahydroacridine-1,8-dione
• CAS: 330472-22-5
• 化学式: C₂₃H₂₆BrNO₂
• 分子量: 428.369
• InChiKey: JCAWEFSPUMOZHL-UHFFFAOYSA-N

物化性质

• 熔点：
  305-307 °C(Solv: ethanol (64-17-5))
• 沸点：
  543.4±50.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.42
• 重原子数：
  27.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  46.17
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  9-(3-bromophenyl)-3,3,6,6-tetramethyl-3,4,6,7-tetrahydroacridine-1,8(2H,5H,9H,10H)-dione 在 dipotassium peroxodisulfate 、 silver nitrate 作用下， 以 二甲基亚砜 为溶剂， 以89 %的产率得到9-(3-Bromophenyl)-3,3,6,6-tetramethyl-2,4,5,7-tetrahydroacridine-1,8-dione
  参考文献：
  名称：

  通过室温 C(sp3)-N 裂解/芳构化反应一锅法高效合成稠合喹啉类似物

  摘要：

  N , N-二甲基苯胺一锅法转化为稠合喹啉衍生物是通过连续氧化环化和伴随的 C(sp 3 )–N 裂解/芳构化反应实现的。该转化在室温下的空气气氛下成功进行。机理研究表明该反应遵循自由基途径。计算机研究表明，合成的分子表现出良好的 caspase-3 抑制活性。

  DOI：

  10.1039/d3nj05462d
• 作为产物：
  描述：

  5,5-二甲基-1,3-环己二酮 在 ammonium acetate 作用下， 以 水 为溶剂， 反应 7.5h， 生成 9-(3-bromophenyl)-3,3,6,6-tetramethyl-3,4,6,7-tetrahydroacridine-1,8(2H,5H,9H,10H)-dione
  参考文献：
  名称：

  在水性介质中有效合成吖啶二酮

  摘要：

  摘要 使用水作为反应介质，无需色谱纯化，就可以分两步高效合成吖啶二酮。第一步涉及二甲酮与乙酸铵反应以在水中产生烯胺酮，其在与各种醛进一步反应时产生在水性介质中的吖啶二酮。该反应的优点是用水作溶剂，不添加催化剂，产品收率高，纯度好。图形概要

  DOI：

  10.1080/00397911.2017.1304556

文献信息

• USY-zeolite catalyzed synthesis of 1,4-dihydropyridines under microwave irradiation: structure and recycling of the catalyst
  作者：Leonardo H.R. Alponti、Monize Picinini、Ernesto A. Urquieta-Gonzalez、Arlene G. Corrêa

  DOI：10.1016/j.molstruc.2020.129430

  日期：2021.3

  therapeutically and also as visible‐light photoredox catalysts. In this work we report the application of an ultra-stable (US) Y zeolite as a promising green catalyst in the synthesis of a series of 1,4-dihydropyridines under microwave irradiation. Using the optimized reaction conditions, 21 compounds were prepared in 64-96% isolated yields. The recovery and recycle of the USY zeolite are also reported as well

  摘要 Hantzsch 三组分反应是最著名的多组分反应，可提供已用于治疗的二氢吡啶类化合物，也可用作可见光光氧化还原催化剂。在这项工作中，我们报告了超稳定 (US) Y 沸石作为一种有前途的绿色催化剂在微波辐射下合成一系列 1,4-二氢吡啶中的应用。使用优化的反应条件，以 64-96% 的分离产率制备了 21 个化合物。还报告了 USY 沸石的回收和再循环及其完全表征。
• Green and efficient synthesis of acridine-1,8-diones and hexahydroquinolines via a KH2PO4 catalyzed Hantzsch-type reaction in aqueous ethanol
  作者：Shi-Jun Yü、Si Wu、Xin-Min Zhao、Cheng-Wei Lü

  DOI：10.1007/s11164-016-2814-2

  日期：2017.5

  A simple, clean, and economical methodology for the synthesis of acridine-1,8-dione and hexahydroquinoline derivatives via Hantzsch-type condensation has been described. This study highlights the development of a new green pathway for the preparation of substituted 1,4-dihydropyridines derivatives. The mild, cheap, and nontoxic potassium dihydrogen phosphate (KH2PO4) is proved to be an efficient catalyst for the above multi-component reaction to get excellent yields. Widely available and mostly benign catalyst, eco-friendly solvent, and easy purification are among the several attractive features.

  本文描述了一种通过Hantzsch型缩合反应合成吖啶-1,8-二酮和六氢喹啉衍生物的简单、清洁且经济的方法。该研究突出了为制备取代的1,4-二氢吡啶衍生物开发的新型绿色合成途径。温和、廉价且无毒的磷酸二氢钾（KH2PO4）被证明是上述多组分反应的有效催化剂，能够获得优异的产率。广泛可用且基本上无害的催化剂、环保溶剂以及容易的纯化过程是该方法的几个吸引人的特点。
• Nanocrystalline TiO₂ , via green combustion synthesis, as an efficient and reusable catalyst for the preparation of 1,8-dioxooctahydroxanthenes and 1,8-dioxodecahydroacridines
  作者：Esmaiel Eidi、Mohammad Zaman Kassaee、Zahra Nasresfahani

  DOI：10.1002/aoc.3370

  日期：2015.12

  Nanocrystalline TiO2 is synthesized using a green combustion method and used as a recyclable catalyst for the one‐pot multicomponent synthesis of 1,8‐dioxodecahydroacridines and 1,8‐dioxooctahydroxanthenes, under solvent‐free conditions. This method is mild, environmentally friendly, inexpensive and highly effective for obtaining good to excellent yields of the products. Copyright © 2015 John Wiley

  纳米晶TiO 2是通过绿色燃烧方法合成的，可在无溶剂条件下用作1，8-二氧杂脱氧氢化ac啶和1,8-二氧杂八氧杂蒽的单锅多组分合成的可回收催化剂。该方法温和，环保，便宜且对获得良好或优异的产品收率非常有效。版权所有©2015 John Wiley＆Sons，Ltd.
• Novel Brønsted Acidic Ionic Liquid ([CMIM][CF3COO]) Prompted Multicomponent Hantzsch Reaction for the Eco-Friendly Synthesis of Acridinediones: An Efficient and Recyclable Catalyst
  作者：Dayanand Patil、Dattatray Chandam、Abhijeet Mulik、Prasad Patil、Surybala Jagadale、Rajni Kant、Vivek Gupta、Madhukar Deshmukh

  DOI：10.1007/s10562-014-1202-z

  日期：2014.5

  AbstractsA novel, highly efficient and recyclable Brønsted acidic ionic liquid ([CMIM][CF3COO]) has been successfully implemented for the synthesis of acridinediones in aqueous media. Recyclability of novel catalyst, high yields, use of environmentally benign aqueous media as solvent, simple product isolation, high atom economy and sidestep to column chromatography are the noteworthy features of this

  摘要：一种新型、高效且可回收的布朗斯台德酸性离子液体 ([CMIM][CF3COO]) 已成功用于在水性介质中合成吖啶二酮。新型催化剂的可回收性、高产率、使用对环境无害的水性介质作为溶剂、产品分离简单、原子经济性高和对柱色谱的回避是该协议的显着特点。该协议能够以良好到出色的产量生产广泛的吖啶二酮库。此外，通过单晶 X 射线衍射证实了 4c 和 4s 衍生物的分子结构和相对立体化学。
• Nano-TiO₂as an Efficient Catalyst for Tandem Knoevenagel-Michael-Cyclocondensation Reaction of Dimedone with Aromatic Aldehydes and Ammonium Acetate or Aromatic Amines under Solvent-free Conditions
  作者：Ardeshir Khazaei、Ahmad Reza Moosavi-Zare、Zahra Mohammadi、Vahid Khakyzadeh、Javad Afsar

  DOI：10.1002/jccs.201500384

  日期：2016.2

  and successfully applied as an efficient and heterogeneous catalyst in the synthesis of 1,8‐dioxo‐decahydroacridines via the one‐pot multi‐component condensation reaction of dimedone with aromatic aldehydes and ammonium acetate or aromatic amines under mild and solvent‐free conditions.

  通过X射线衍射（XRD），扫描电子显微镜（SEM），透射电子显微镜（TEM）等多种技术对锐钛矿型和金红石型TiO 2纳米颗粒进行了表征和研究，并成功地将其用作高效，多相催化剂。在温和且无溶剂的条件下，通过二甲酮与芳族醛和乙酸铵或芳族胺的单锅多组分缩合反应得到1,8-二氧代十氢hydro啶。