3,4,6,7-tetrahydro-3,3,6,6-tetramethyl-9-(pyridin-2-yl)acridine-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-3,3,6,6-tetramethyl-9-(pyridin-2-yl)acridine-1,8(2H,5H,9H,10H)-dione
• 英文别名: 3,4,6,7-tetrahydro-3,3,6,6-tetramethyl-9-(pyridin-2-yl)acridine-1,8(2H,5H,9H,10H)dione；3,3,6,6-tetramethyl-9-(pyridin-2-yl)-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione；3,3,6,6-Tetramethyl-9-pyridin-2-yl-2,4,5,7,9,10-hexahydroacridine-1,8-dione
• 化学式: C₂₂H₂₆N₂O₂
• 分子量: 350.461
• InChiKey: QQWDKTDFXHSQBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  59.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,3,6,6- tetramethyl-9-(pyridin-2-yl)-3,4,6,7-tetrahydro-2H-xanthene-1,8(5H,9H)-dione 在 zinc ferrite 、 氨 作用下， 以 水 为溶剂， 反应 3.0h， 以88%的产率得到3,4,6,7-tetrahydro-3,3,6,6-tetramethyl-9-(pyridin-2-yl)acridine-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

• 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。
• 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。
• Evaluation of sodium acetate trihydrate–urea DES as a benign reaction media for the Biginelli reaction. Unexpected synthesis of methylenebis(3-hydroxy-5,5-dimethylcyclohex-2-enones), hexahydroxanthene-1,8-diones and hexahydroacridine-1,8-diones
  作者：Camilo A. Navarro、Cesar A. Sierra、Cristian Ochoa-Puentes

  DOI：10.1039/c6ra13848a

  日期：——

  In this work, the low melting mixture sodium acetate trihydrate–urea was synthesized and the eutectic composition was determined and characterized. The performance of this deep eutectic solvent on the Biginelli reaction was evaluated.

  在这项工作中，合成了低熔点混合物醋酸钠三水合物-尿素，并确定并表征了共熔组成。评估了这种深共熔溶剂在Biginelli反应中的性能。
• A new MCM-41 supported HPF6 catalyst for the library synthesis of highly substituted 1,4-dihydropyridines and oxidation to pyridines: report of one-dimensional packing towards LMSOMs and studies on their photophysical properties
  作者：Suman Ray、Mike Brown、Asim Bhaumik、Arghya Dutta、Chhanda Mukhopadhyay

  DOI：10.1039/c3gc40441b

  日期：——

  a library synthesis of highly substituted 1,4-dihydropyridines (1,4-DHPs). The 1,4-DHPs are further oxidized to pyridines with aqueous H2O2 as stoichiometric oxidant which is considered as an abundant and green oxidant. The pyridines spontaneously generate low molecular mass self-aggregated organic materials (LMSOMs). Their one-dimensional packing and interesting photophysical properties are reported

  使用一系列复杂的分析技术，例如BET，XRD，HRTEM，EDX，29 Si MAS NMR，TGA，FTIR和pH测量，合成并表征了一种新型的均相MCM-41二氧化硅负载型HPF 6催化剂。通过高度取代的1,4-二氢吡啶（1,4-DHP）的文库合成，探索了二氧化硅-HPF 6的广泛适用性。1,4-DHPs被H 2 O 2水溶液进一步氧化为吡啶作为化学计量的氧化剂，被认为是一种丰富的绿色氧化剂。吡啶自发产生低分子量的自聚集有机物质（LMSOM）。据报道它们的一维堆积和有趣的光物理性质。使用水作为溶剂进行合成对于其可持续的绿色影响至关重要。此外，二氧化碳和水是唯一的副产物，这增加了它的吸引力。该二氧化硅-HPF 6催化剂即使暴露于环境气氛10天后仍保持其活性。
• An Efficient and Fast Procedure for the Hantzsch Dihydropyridine Synthesis under Microwave Conditions
  作者：Liselotte Öhberg、Jacob Westman

  DOI：10.1055/s-2001-16043

  日期：——

  A single-mode microwave cavity synthesizer with temperature and pressure control was used to accelerate the Hantzsch synthesis of 4-aryl and 4-alkyl-2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarboxylates. In comparison with both conventional methods and microwave-assisted reactions performed in a domestic microwave oven, shorter reaction times and higher yields were obtained. The improved yields under microwave conditions made it possible to synthesize a small library, with acceptable purity.

  利用具有温度和压力控制功能的单模微波腔合成器加速了 4-芳基和 4-烷基-2,6-二甲基-1,4-二氢-3,5-吡啶二羧酸盐的汉兹合成。与传统方法和在家用微波炉中进行的微波辅助反应相比，反应时间更短，产率更高。在微波条件下，产率的提高使得合成具有可接受纯度的小型化合物库成为可能。