3,3,6,6-tetramethyl-9-(thiophen-2-yl)-3,4,6,7-tetrahydroacridine-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: 3,3,6,6-tetramethyl-9-(thiophen-2-yl)-3,4,6,7-tetrahydroacridine-1,8(2H,5H,9H,10H)-dione
• 英文别名: 3,4,6,7-tetrahydro-3,3,6,6-tetramethyl-9-(thiophen-2-yl)acridine-1,8(2H,5H,9H,10H)-dione；3,3,6,6-tetramethyl-9-(thiophen-2-yl)-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione；3,3,6,6-tetramethyl-9-(thiophen-2-yl)-3,4,6,7,9,10-hexahydroacridine-1,8-(2H,5H)-dione；3,3,6,6-tetramethyl-9-(thiophen-2-yl)-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione；3,3,6,6-tetramethyl-1,8-dioxo-9-(2-thienyl)-1,2,3,4,5,6,7,8,9,10-decahydroacridine；3,3,6,6-tetramethyl-9-(2-thienyl)-3,4,6,7,9,10-hexahydroacridine-1(2H),8(5H)-dione；3,3,6,6-tetramethyl-9-(2-thienyl)-3,4,6,7,9,10-hexahydro-1,8(2H,5H)-acridinedione；3,3,6,6-tetramethyl-9-thiophen-2-yl-2,4,5,7,9,10-hexahydroacridine-1,8-dione
• 化学式: C₂₁H₂₅NO₂S
• mdl: MFCD00175701
• 分子量: 355.501
• InChiKey: GBBPKDNIGRBITI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  74.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-噻吩甲醛 、 3-氨基-5,5-二甲基-2-环己烯-1-酮 在 phosphorus pentoxide 作用下， 以 异丙醇 为溶剂， 以86%的产率得到3,3,6,6-tetramethyl-9-(thiophen-2-yl)-3,4,6,7-tetrahydroacridine-1,8(2H,5H,9H,10H)-dione
  参考文献：
  名称：

  摘要：

  DOI：

  10.1023/a:1010484013306

文献信息

• Synthesis of 1,8-Dioxo-decahydroacridine Derivatives <i>via</i> Ru-Catalyzed Acceptorless Dehydrogenative Multicomponent Reaction
  作者：Nandita Biswas、Dipankar Srimani

  DOI：10.1021/acs.joc.1c01075

  日期：2021.7.16

  A Ru-catalyzed acceptorless dehydrogenative multicomponent reaction has been developed. This reaction offers a cost-effective and simple operational strategy to synthesize biologically active 1,8-dioxodecahydroacridine derivatives. The protocol provides a wide range of substrate scope and various functional groups are also well tolerated under the reaction condition. To shed light on the mechanistic

  已经开发了 Ru 催化的无受体脱氢多组分反应。该反应为合成具有生物活性的 1,8-二氧十氢吖啶衍生物提供了一种经济高效且简单的操作策略。该协议提供了广泛的底物范围，并且在反应条件下也可以很好地耐受各种官能团。为了阐明机械和动力学研究，进行了一些对照实验和氘标记实验。还介绍了一个与时间相关的产品分布实验，并进行了反应放大以突出该策略的实际效用。
• 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。
• 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。
• Acetic acid as an efficient catalyst for synthesis of 1,8-dioxo-octahydroxanthenes and 1,8-dioxo-decahydroacridines
  作者：Nourallah Hazeri、Amin Masoumnia、Malek Taher Mghsoodlou、Sajjad Salahi、Mehrnoosh Kangani、Samira Kianpour、Shiva Kiaee、Jasem Abonajmi

  DOI：10.1007/s11164-013-1516-2

  日期：2015.7

  1,8-Dioxo-octahydroxanthenes have been synthesized in good yields by reaction of arylaldehydes and dimedone in the presence of a catalytic amount of acetic acid, without use of any additional co-catalyst, under solvent-free, thermal conditions. We also report preparation of 1,8-dioxo-decahydroacridines by reaction of arylaldehydes, dimedone, and amines or ammonium acetate under solvent-free, thermal

  在无溶剂的热条件下，在催化量的乙酸存在下，不使用任何其他助催化剂的情况下，通过芳基醛与二甲酮的反应，可以高收率合成1,8-二氧-八氧杂蒽。我们还报告了在相同的催化剂存在下，在无溶剂的热条件下，通过芳基醛，二甲酮和胺或乙酸铵的反应制备1,8-二氧-十氢hydro啶。
• 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。