9-(2-hydroxyphenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydro-1,8(2H,5H)-acridinedione | 136231-39-5

• 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-(2-hydroxyphenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydro-1,8(2H,5H)-acridinedione
• 英文别名: 3,3,6,6-tetramethyl-9-(2-hydroxyphenyl)-3,4,6,7,9,10-hexahydroacridine-1,8-dione；9-(2'-hydroxyphenyl)-3,3,6,6-tetramethyl-2,4,5,7,9,10-hexahydro-acridine-1,8-dione；9-(2-hydroxyphenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydro-2H,5H-acridine-1,8-dione；9-(2-hydroxyphenyl)-3,3,6,6-tetramethyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione；9-(2-hydroxyphenyl)-3,3,6,6-tetramethyl-2,4,5,7,9,10-hexahydroacridine-1,8-dione
• CAS: 136231-39-5
• 化学式: C₂₃H₂₇NO₃
• mdl: MFCD01090126
• 分子量: 365.472
• InChiKey: WQVFCAVYWQJFRA-UHFFFAOYSA-N

物化性质

• 熔点：
  307-309 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  505.7±50.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  水杨醛 、 5,5-二甲基-1,3-环己二酮 在 ammonium acetate 作用下， 以 neat (no solvent) 为溶剂， 反应 0.42h， 以92%的产率得到9-(2-hydroxyphenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydro-1,8(2H,5H)-acridinedione
  参考文献：
  名称：

  纳米晶TiO2，通过绿色燃烧合成，作为一种高效且可重复使用的催化剂，用于制备1,8-二氧杂八氢氧杂蒽和1,8-二氧杂十二碳hydro啶

  摘要：

  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.

  DOI：

  10.1002/aoc.3370

文献信息

• 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.
• Melamine-formaldehyde resin supported H⁺-catalyzed three-component synthesis of 1,8-dioxo-decahydroacridine derivatives in water and under solvent-free conditions
  作者：Ramin Rezaei、Reza Khalifeh、Maryam Rajabzadeh、Liela Dorosty、Mohammad Mahdi Doroodmand

  DOI：10.1515/hc-2012-0053

  日期：2013.3.1

  Abstract A convenient and practical synthesis of 1,8-dioxo-decahydroacridine derivatives using various aldehydes, 5,5-dimethyl-1,3-cyclohexanedione and thiourea in water, was successfully carried out in the presence of melamine-formaldehyde resin supported H+ (MFRH) as a catalyst. Under solvent-free conditions, rapid and efficient synthesis of 1,8-dioxo-decahydroacridine and N-substituted 1,8-dioxo-decahydroacridine

  摘要 在三聚氰胺-甲醛树脂负载的 H+ 存在下，使用各种醛、5,5-二甲基-1,3-环己二酮和硫脲在水中方便实用地合成了 1,8-二氧十氢吖啶衍生物（ MFRH) 作为催化剂。在无溶剂条件下，以醋酸铵和芳香胺为氮源，也可以快速高效地合成1,8-二氧十氢吖啶和N-取代的1,8-二氧十氢吖啶衍生物。
• 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。
• Magnetically Separable Recyclable Nano-ferrite Catalyst for the Synthesis of Acridinediones and Their Derivatives under Solvent-free Conditions
  作者：Palla Mahesh、Kolakaluri Guruswamy、Bhagavathula Subrahmanya Diwakar、Bhoomireddy Rama Devi、Yellajyosula Lakshmi Narasimha Murthy、Pratap Kollu、Sri Venkata Narayan Pammi

  DOI：10.1246/cl.150503

  日期：2015.10.5

  Catalytic activity of nano-ferrite is explored in the synthesis of acridinedione and their derivatives under benign conditions; a greener protocol is reported in terms of excellent yield and recyclability under solvent-free reactions without using any additive/cocatalyst. Nano-ferrite catalyst is synthesized using sol–gel process at low temperatures. X-ray diffraction (XRD) and transmission electron microscopy (TEM) results exhibit cubic phase of maghemite (γ-Fe2O3) with average particle size of 18 nm. Furthermore, the catalyst can be easily separated using an external magnet and reused up to nine cycles without any significant loss of activity.

  纳米铁氧体在温和条件下合成吖啶二酮及其衍生物的催化活性得到了探讨；在无溶剂反应中，报告了一种更环保的方案，具有优异的产率和可回收性，无需使用任何添加剂或助催化剂。纳米铁氧体催化剂采用溶胶-凝胶法在低温下合成。X射线衍射（XRD）和透射电子显微镜（TEM）结果显示，具有立方相的磁铁矿（γ-Fe2O3）平均粒径为18纳米。此外，该催化剂可以通过外部磁铁轻松分离，并在九个循环内重复使用，活性几乎没有显著损失。
• Polyethylene glycol-mediated synthesis of decahydroacridine-1,8-diones catalyzed by ceric ammonium nitrate
  作者：Mazaahir Kidwai、Divya Bhatnagar

  DOI：10.2478/s11696-010-0070-2

  日期：2010.1.1

  Polyethylene glycol was found to be an inexpensive non-toxic and effective medium for one pot synthesis of high yields of decahydroacridine-1,8-diones in the presence of ceric ammonium nitrate as the catalyst. Moreover, the solvent can be recovered and reused.

  发现聚乙二醇是一种廉价的无毒且有效的介质，用于在硝酸铈铵作为催化剂的情况下一锅合成高产率的十氢ac啶-1,8-二酮。而且，溶剂可以被回收和再利用。