3,3,6,6-tetramethyl-9-(3,4-methylenedioxyphenyl)-1,2,3,4,5,6,7,8,9,10-decahydroacridin-1,8-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: 3,3,6,6-tetramethyl-9-(3,4-methylenedioxyphenyl)-1,2,3,4,5,6,7,8,9,10-decahydroacridin-1,8-dione
• 英文别名: 3,3,6,6-tetramethyl-9-piperonyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione；9-(benzo[d][1,3]dioxol-5-yl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione；9-(benzo[d][1,3]dioxol-5-yl)-3,4,6,7(2H,5H,9H,10H)-tetrahydro-3,3,6,6-tetramethylacridine-1,8-dione；9-(1,3-benzodioxol-5-yl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydro-1,8(2H,5H)-acridinedione；9-(1,3-benzodioxol-5-yl)-3,3,6,6-tetramethyl-2,4,5,7,9,10-hexahydroacridine-1,8-dione
• 化学式: C₂₄H₂₇NO₄
• 分子量: 393.483
• InChiKey: YUDCYZDTZSCVSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  29
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,3,6,6-tetramethyl-9-(3,4-methylenedioxyphenyl)-1,2,3,4,5,6,7,8,9,10-decahydroacridin-1,8-dione 在 air 、 pyrene and triazine-based porous organic polymer 作用下， 以 乙腈 为溶剂， 以80 %的产率得到
  参考文献：
  名称：

  Development of Porous Organic Polymers as Metal‐Free Photocatalysts for the Aromatization of N‐Heterocycles

  摘要：

  摘要 多孔有机聚合物（POPs），尤其是共价三嗪框架（CTFs），正被开发为下一代无金属异相光催化剂。然而，目前获得这些光活性持久性有机聚合物的许多合成路线都需要昂贵的单体并依赖贵金属催化剂，因此阻碍了它们的广泛应用。在这项研究中，我们通过路易斯酸催化聚合反应，从简单的非官能化芳香族结构单元合成了一系列持久性有机污染物。所获得的材料首次被用作 N-杂环芳香化的异相光催化剂。使用活性最高的材料 CTF-Pyr（由具有光活性的芘和三嗪分子组成），可以获得多种吡啶、二氢喹啉-5-酮、四氢吖啶-1,8-二酮和吡唑，收率极高（70-99%）。此外，这些反应都是在非常温和的条件下，利用空气在室温下进行的，突出了这些材料作为绿色转化催化剂的潜力。

  DOI：

  10.1002/cctc.202301205
• 作为产物：
  描述：

  胡椒醛 、 5,5-二甲基-1,3-环己二酮 在 ammonium acetate 、 1-丁基-3-甲基咪唑溴盐 作用下， 反应 0.5h， 以86%的产率得到3,3,6,6-tetramethyl-9-(3,4-methylenedioxyphenyl)-1,2,3,4,5,6,7,8,9,10-decahydroacridin-1,8-dione
  参考文献：
  名称：

  醛，胺和二甲酮在离子液体中的三组分反应有效合成多氢ac啶衍生物

  摘要：

  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。

  DOI：

  10.1002/jhet.5570450303

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。
• Assessment and use of two silicon carbide multi-well plates for library synthesis and proteolytic digests using microwave heating
  作者：Lauren M. Stencel、Chad M. Kormos、Keri B. Avery、Nicholas E. Leadbeater

  DOI：10.1039/b902112d

  日期：——

  The use of two silicon carbide plates is reported for the preparation of three libraries of organic molecules using microwave heating. In addition, a preliminary study has been carried out, showing that one of the plates can also be used in a proteomics setting. Both the 24-position and 48-position plates heated evenly when irradiated with microwave energy. The 48-position plate was used to prepare a library of N-aryl functionalized β-amino esters via an aza-Michael reaction between anilines and Michael acceptors. The 24-position plate was used to prepare a library of biaryls via a Suzuki coupling methodology and a library of 1,4-dihydropyridines via a Hantzsch synthesis. The 48-position plate was also used to perform the proteolytic digestion of insulin chain B by trypsin.

  报道了使用两个碳化硅板通过微波加热制备三种有机分子库的方法。此外，还进行了初步研究，表明其中一个板材也可用于蛋白质组学环境。两个板材在微波辐射下均能均匀加热，即24位板和48位板。48位板被用于通过苯胺与迈克尔受体之间的氮迈克尔反应制备N-芳基功能化的β-氨基酯库。24位板被用于通过铃木偶联方法制备联苯库，以及通过汉奇合成制备1,4-二氢吡啶库。48位板还用于通过胰蛋白酶对胰岛素B链进行蛋白水解消化。
• 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。
• Microwave induced new route to acridine and quinazoline derivatives using TLC plates
  作者：M. Kidwai、S. Saxena、R. Mohan

  DOI：10.1002/jhet.5570420435

  日期：2005.5

  Microwave (MW) assisted synthesis of acridine and quinazoline derivatives was performed on thin layer chromatography (TLC) plates. This versatile, simple and economical green methodology is readily amenable to parallel synthesis of acridine and quinazoline compound libraries.

  微波（MW）辅助合成的cr啶和喹唑啉衍生物在薄层色谱（TLC）板上进行。这种通用，简单且经济的绿色方法很容易适用于cr啶和喹唑啉化合物库的并行合成。