3,4,6,7-tetrahydro-9-(3,4-dimethoxyphenyl)-3,3,6,6-tetramethylacridine-1,8(2H,5H,9H,10H)-dione

• 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: 3,4,6,7-tetrahydro-9-(3,4-dimethoxyphenyl)-3,3,6,6-tetramethylacridine-1,8(2H,5H,9H,10H)-dione
• 英文别名: 9-(3,4-Dimethoxyphenyl)-3,3,6,6-tetramethyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione；9-(3,4-dimethoxyphenyl)-3,3,6,6-tetramethyl-2,4,5,7,9,10-hexahydroacridine-1,8-dione
• 化学式: C₂₅H₃₁NO₄
• mdl: MFCD00520521
• 分子量: 409.525
• InChiKey: XOMLEJRQARUTCK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,3,6,6-tetramethyl-9-(3,4-dimethoxyphenyl)-1,8-dioxooctahydroxanthene 在 zinc ferrite 、 氨 作用下， 以 水 为溶剂， 反应 3.0h， 以93%的产率得到3,4,6,7-tetrahydro-9-(3,4-dimethoxyphenyl)-3,3,6,6-tetramethylacridine-1,8(2H,5H,9H,10H)-dione
  参考文献：
  名称：

  Heterogeneous ditopic ZnFe₂O₄catalyzed synthesis of 4H-pyrans: further conversion to 1,4-DHPs and report of functional group interconversion from amide to ester

  摘要：

  成功制备、表征并应用了一种稳定且对环境友好的ZnFe2O4纳米粉，在水相中实现了4H-吡喃的一锅法三组分合成。ZnFe2O4催化剂同时提供了反应所需的酸性（Fe3+）和碱性（O2−）功能。该方法的优势在于其简单性、成本效益、环境友好性以及更易于放大进行大规模合成。水既被用作反应介质，也被用作催化剂的合成介质。此外，水是唯一的副产品。本报告提出了一种应用4H-吡喃合成1,4-二氢吡啶（1,4-DHPs）的方法。这是首次尝试从4H-吡喃-3-甲酰胺合成4H-吡喃-3-羧酸酯。在有机合成中，从酰胺到酯的功能团转换是罕见的。

  DOI：

  10.1039/c3gc42095g

文献信息

• A Novel Reaction of Aldeoxime with Dimedone Under Microwave Irradiation
  作者：Shujang Tu、Yuan Gao、Chunbao Miao、Tuanjie Li、Xiaojing Zhang、Songlei Zhu、Fang Fang、Daqing Shi

  DOI：10.1081/scc-120030317

  日期：2004.12.31

  Abstract The reaction of aldeoxime with dimedone and ammonium acetate in glycol under microwave irradiation has been carried out, elimination and cyclization happened and acridine derivatives were obtained. The structure of the product has been thoroughly studied by x‐ray crystallographic analysis.

  摘要 在微波辐射下，醛肟与二甲酮和乙酸铵在乙二醇中反应，发生消除环化反应，得到吖啶衍生物。产品的结构已经通过 X 射线晶体学分析进行了彻底的研究。
• Catalytic application of sulfonic acid‐functionalized titana‐coated magnetic nanoparticles for the preparation of 1,8‐dioxodecahydroacridines and 2,4,6‐triarylpyridines via anomeric‐based oxidation
  作者：Mohammad Ali Zolfigol、Fatemeh Karimi、Meysam Yarie、Morteza Torabi

  DOI：10.1002/aoc.4063

  日期：2018.2

  We have developed green, efficient and powerful protocols for the preparation of 2,4,6‐triarylpyridines and 1,8‐dioxodecahydroacridines in the presence of Fe3O4@TiO2@O2PO2(CH2)2NHSO3H as a sulfonic acid‐functionalized titana‐coated magnetic nanoparticle catalyst under mild and solvent‐free reaction conditions. These protocols furnished the desired products in short reaction times with good to high

  我们已开发出在Fe 3 O 4 @TiO 2 @O 2 PO 2（CH 2）2 NHSO 3存在下制备2,4,6-三芳基吡啶和1,8-二氧杂脱氢hydro啶的绿色，高效且有力的方法H在温和无溶剂的反应条件下作为磺酸官能化的钛包覆磁性纳米粒子催化剂。这些方案可在较短的反应时间内提供所需的产物，并具有良好的高收率（对于2,4,6-三芳基吡啶，为20–40分钟和80–86％；对于2,4,6-三芳基吡啶为15–90分钟和80–93％ 1,8-二氧杂十二烷基hydro啶）。机械合成2,4,6-三芳基吡啶的最后一步是通过基于异头的氧化进行的。同样，在经过仔细研究的单罐多组分反应中，具有高周转数和周转频率的纳米磁性核-壳催化剂可以循环再利用。
• 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。
• An efficient synthesis of polyhydroacridine derivatives by the three-component reaction of aldehydes, amines and dimedone in ionic liquid
  作者：Da-Qing Shi、Sai-Nan Ni、Fang-Yang、Jing-Wen Shi、Guo-Lan Dou、Xiao-Yue Li、Xiang-Shan Wang

  DOI：10.1002/jhet.5570450303

  日期：2008.5

  In this paper the preparation of 3,3,6,6-tetramethyl-9,10-diaryl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione derivatives from aldehydes, aromatic amines and 5,5-dimethyl-1,3-cyclohexanedione in 1-n-butyl-3-methylimidazolium bromide ([bmim]Br) is described. The structures of these compounds were characterized by elemental analysis, IR and 1H NMR spectra and further confirmed by single crystal X-ray

  本文制备了3,3,6,6-四甲基-9,10-二芳基-1,2,3,4,5,6,7,8,9,10-十氢ac啶-1,8-二酮衍生物描述了由醛，芳族胺和5，5-二甲基-1，3-环己二酮在1-正丁基-3-甲基咪唑鎓溴化物（[bmim] Br）中的组成。这些化合物的结构通过元素分析，IR和1 H NMR光谱进行表征，并通过单晶X射线衍射分析进一步证实。
• Unexpected and Green Synthesis of Azapodophyllotoxin Derivatives via Microwave-Assisted Multicomponent Reactions in Ammonia Water
  作者：Feng Shi、Ning Ma、Yan Zhang、Ge Zhang、Bo Jiang、Shujiang Tu

  DOI：10.1080/00397910902964825

  日期：2009.12.30

  An unexpected and green synthesis of azapodophyllotoxin derivatives was realized via microwave-assisted multicomponent reactions of dimedone, tetronic acid, and aromatic aldehydes in ammonia water. This protocol has the advantages of environmental friendliness, short reaction time, good yields, low cost, and easy operation.

  通过二甲酮、丁酮酸和芳香醛在氨水中的微波辅助多组分反应，实现了氮杂鬼臼毒素衍生物的出人意料的绿色合成。该方案具有环境友好、反应时间短、收率好、成本低、操作简便等优点。